A melting pot of eccentric culture, world-class sport, an enviable food scene (did someone say deep-dish pizza?), and a rich and vibrant history, Chicago is a quintessential Midwest destination for anyone in search of an action-packed vacation.
Straddling the shimmering shoreline of Lake Michigan and packed with top-notch attractions, Chicago is a city that has a little splash of something for everyone. With world-renowned museums, diverse art galleries, thrilling amusement rides, awe-inspiring architecture (and the home of Frank Lloyd Wright), and legendary sports teams (shout out to the Cubs finally breaking their drought), it’s easy to see why millions of people flock to this urban metropolis year after year.
And with so many options to choose from when it comes to places to visit in Chicago, you’ll never be short of ways to fill your itinerary. So, what are you waiting for? Start planning your trip to Chicago – the Windy City is waiting for you!
1 – 360 Chicago Observation Deck
Towering more than 1,000 feet above The Windy city, on the 94th floor of what was once the tallest building outside of New York City, 360 Chicago atop the former John Hancock Center dishes up spellbinding views in every direction.
Take in the busy streets of the Magnificent Mile below, the shimmering waters of Lake Michigan to the north and east, and the postcard-worthy array of skyscrapers (including the 1,451-foot Willis Tower to the south, then cap off your visit with a drink at the bar or snack at the cafe.
For a different perspective and mad adrenaline rush, test out TILT — a mechanized room full of floor-to-ceiling glass windows that angle 30 degrees over the building’s edge.
Hot tip: to experience three different, truly spectacular views – daytime, twilight, and twinkling nighttime — arrive about an hour before sunset.
2 – Shedd Aquarium
Straddling Lake Michigan’s shoreline of the southern end of the sprawling, elongated Grant Park, the Shedd Aquarium is a Chicago family favorite, and one of the most popular aquariums in the world.
Home to no less than 32,000 animals of all shapes, sizes, and colors (and fear factors) – from sea otters and seahorses, to beluga whales, reef sharks, and aptly-named Giant Pacific octopus — The Shedd’s galleries showcase diverse aquatic creatures from all corners of the planet, with a focus on education, conservation, and curiosity!
A surefire hit for kids and adults alike, this enormous facility (it was once the largest indoor attraction in the world) boasts highlights including a 360-degree walk-around Caribbean reef, a stingray touch pool where you can meet the ominous critters up close, a beluga whale habitat complete with underwater viewing tunnels, and a range of VIP meet-and-greet opportunities!
Don’t miss the 4D theater, and consider opting for the Beluga Encounter or Shark Feeding Experience!
3 – Navy Pier
A beacon of fun and frivolity on Chicago’s glittering Lake Michigan waterfront, the 3,300-foot-long Navy Pier is a sprawling hub of family-friendly attractions that can’t help but delight.
Kick-off your visit with a ride on the Centennial Wheel then wander down the 50 acres worth of parks, restaurants, docks, shops, and the tropical Crystal Gardens.
Traveling with kids in tow? Both the Chicago Children’s Museum (always free for kids) and the IMAX theater and sure to keep them entertained for at least a couple of hours. Fancy a feed? Follow the locals with a food tasting and cultural walking tour or dig into a hefty slice of Chicago deep-dish pizza at Giordano’s!
While the area thrives year-round, during the summer months the atmosphere is electric with live music concerts, food trucks, and street performers; around the holidays it transforms into a winter wonderland of ice skating, mulled wine, and special events
4 – Michigan Avenue’s Magnificent Mile
The city’s focal point for food, fashion, and fun is the world-famous Magnificent Mile – AKA Michigan Avenue.
The 13-block stretch of street runs for about a mile (hence the name) along Chicago’s northern waterfront district from the banks of Lake Michigan to Oak Street, passing dozens of department stores, chic hotels, famous museums, and picturesque landmarks en route.
Stroll down this iconic thoroughfare and you’ll uncover some of Chicago’s most renowned buildings such as The Wrigley Building, the John Hancock Center, and Tribune Tower (with its unusual facade made up of more than 150 rocks from sites around the globe) — all interspersed with high-end boutiques like Louis Vuitton and Cartier, speakeasy pubs, and revered underground eateries.
Be sure to wander over the DuSable Bridge, and, if you’re keen to learn a thing or two about the area’s history, culture, and hidden gems, consider signing up for a locally-led walking tour.
5 – Zoos
Welcoming locals and visitors alike, Chicago’s two most renowned zoos — Lincoln Park Zoo in the North Side neighborhood and Brookfield Zoo over in Brooklyn — collective house hundreds of species and thousands of animals, with live educational shows, behind-the-scenes tours, reptile houses, and up-close encounters aplenty.
Easily accessed from Downtown by transport or car, the Lincoln Park Zoo is one of the last free zoos in the USA, with has a diverse array of wildlife across its 35 acres – its roughly-1,100 animals includes lions, gorillas, hyenas, and giraffes! Beloved by kids, the Lincoln Park Zoo also offers a children’s farm as well as some lush gardens ideal for a picnic.
Meanwhile, further inland (but worth the drive) Brookfield Zoo has more friendly creatures to check out (close to 2,300 comprised of 450 species) and is sandwiched in between the Brookfield and McCormick Woods, meaning that there’s no shortage of beautiful open space to relax in after a day of wonderful animal experiences.
6 – The Field Museum of Natural History
One for the history buffs and culture vultures, Chicago’s Field Museum of Natural History is a must-see for those interested in Earth science.
Home to more than 40 million fascinating specimens and artifacts — from fingernail-sized fossils to towering dinosaur skeletons — the museum’s exciting yet educational exhibits span everything from ancient Egyptology to geology, botany, and prehistoric evolution – so you can expect plenty of mummies, dinosaurs fossils and detailed dioramas that cover nearly 4.5 billion years worth of history!
A great spot for traveling families too, the museum is particularly interactive, with plenty of hands-on activities to keep kiddos (and kids at heart) entertained.
You’ll find the Museum tucked away at the southern end of Grant Park, around the corner from the Adler Planetarium and Shedd Aquarium — so why not check out a couple of them on the same day?
7 – Millennium Park
Where the action happens and never a moment is dull, Millennium Park is one of Chicago’s best-known urban green spaces.
Located in the heart of Downtown and bordered by Grant Park, this 24.53-acre wonderland was designed as a modern public space for locals and visitors alike, with its many attractions including an outdoor concert venue (Pritzker Pavilion), Insta-worthy fountain (Crown Fountain), sculptures (Cloud Gate – nicknamed “The Bean” for obvious reasons — among others) gardens, an ice rink and plenty more to discover!
This vibrant spot is also home to some fun seasonal activities like open-air movies during summer months and winter ice rinks to boot; so whatever time of year you visit, bet your bottom dollar that long-lasting memories will be made!
8 – Willis Tower SkyDeck
Ready for a killer view? Then head on up to Chicago’s SkyDeck!
Located on the 103rd floor of Willis Tower (formerly Sears Tower), this popular tourist attraction offers visitors sweeping panoramic views of Chicago and its surrounds in all their glory, making it one of the most elevated spots in not just the city but all of America too.
On a clear day, you can see for around 40 miles in every direction – from neighboring states like Wisconsin and Indiana to the vast expanse of Lake Michigan and far beyond!
Tickets are relatively affordable (especially when bought online) and timed entry means that there’s never too long a wait; so whether you want to snap some selfies against the iconic skyline, grab a drink at the bar, or take in an incredible sunset over the Midwest plains, make sure to add this spot to the top of your list of places to visit in Chicago.
9 – Six Flags Great America
A quintessential stop for anyone who even remotely deems themselves a thrill-seeker, Six Flags Great America up in Gurnee, about 50 minutes drive north of Chicago, is a theme park that has it all.
Expect riveting roller coasters, heart-in-your-mouth thrill rides, and refreshing water slides galore in this amusement park that spans over 300 acres of land — plus plenty of kid-friendly activities too!
A great spot for adrenaline junkies, the park is known for its many world-class rides and rollercoasters, including the iconic American Eagle (the world’s tallest and fastest racing wooden coaster), Goliath (which boasts a gut-wrenching 180-foot feet drop), and Raging Bull, the tallest, longest, and fastest coaster at the park.
If you’re looking for something a little tamer, there’s also a charming riverboat ride, Buccaneer Battle, Columbian Carousel, live theater and dance shows, and plenty of restaurants and food trucks; so no matter what your age or thrill-seeking level, you’re sure to have a blast at Six Flags Great America!
10 – Art Institute of Chicago
One for the culture vultures, the world-famous Art Institute of Chicago, located in Downtown’s Grant Park, is one of America’s oldest and largest art museums (operating since the late 1800s and covering a whopping one million square feet).
Here you can explore a mammoth collection of over 300,000 works spanning more than 5000 years – from ancient Egyptian artifacts to over 25,000 pieces of European Decorative Arts, to one of the world’s most significant Impressionist and Post-Impressionist collections outside of France. paintings. Throw in sections dedicated to modern masterpieces by the likes of Picasso, Warhol, and Pollock, and you’ve got to accommodate every artistic fancy!
A true highlight for anyone who has even a passing interest in art (and let’s face it: that’s pretty much everyone), this famous museum also boasts an incredible school where budding artists are given the opportunity to hone their skills in areas like architecture design; so if it tickles your fancy why not check out some classes too?
11 – Chicago Riverwalk
Dedicated to pedestrians and teeming with shopping, dining, entertainment and recreational activities, the Chicago Riverwalk stretches 1.25 miles from Lake Michigan to Lake Street through the heart of Downtown, dishing up cozy cafes, hidden wineries, rowdy bars, and quirky boutiques to boot.
Besides the chance to pop into the shops en route, this charming spot along the city’s scenic waterfront also offers visitors a unique vantage point from which to admire the city’s skyline and, with a walking tour, explore Chicago’s rich history and cultural landscape.
So whether you’re looking for a romantic stroll, an hour or two of people-watching, a spot of afternoon tea, or a day of impromptu walkabout, this waterfront promenade is not to be missed!
12 – North Avenue Beach
Perfect for those toasty summer days, North Avenue Beach is one of the city’s most popular and iconic spots to soak up some sun.
Here you can expect clear views of Chicago’s skyline, a plethora of beach activities (think kayaking, paddleboarding and volleyball), as well as plenty of waterside restaurants where you can kick back with an ice-cold drink and some hearty seafood.
Though it can get a little crowded during the summer months, there’s plenty more sand than people in this shoreline stretch so it seldom feels overwhelming; so grab your sunscreen, your favorite book and prepare for a day of fun in the sun!
Located in Lincoln Park directly on Lake Michigan, it’s also a stone’s throw from myriad hiking and biking trails, as well as the free-to-enter Lincoln Park zoo.
13 – Buckingham Fountain
Standing proud for nearly a century (think of all the postcards it’s frequented in that time) as one of the largest fountains on the planet, Chicago’s Buckingham Fountain is also one of the city’s most recognizable and prominent landmarks.
Set in Chicago’s Grant Park, this iconic landmark was constructed in 1927 to commemorate Clarence Buckingham (a philanthropist who gave his name to the fountain) and has been wowing locals and visitors alike with its impressive 20-minute long water shows ever since, which take place every hour on the hour. So whatever you do, don’t forget your camera!
The basin itself measures an incredible 280 feet in diameter while its central jet shoots a whopping 15,000 gallons of water per minute 150 feet into the air – making it an eye-popping spectacle that couldn’t be missed if you tried.
Hot tip: stroll past the landmark at night for a different perspective – the post-dusk shows are choreographed with brilliant light and music performance!
14 – Lake Michigan
Serving up some of the best views in town, a cruise on Lake Michigan is an absolute must-do for any visitor to Chicago.
Offering everything from quick one-hour trips focused purely on checking off the main landmarks to longer excursions with buffet-style food and strong drinks included, and even VIP romantic cruises, there’s a boat tour for everyone – no matter your budget or timeframe.
What’s more, many of the cruises offer unbeatable perspectives of iconic landmarks you won’t find from land, like Navy Pier, Willis Tower (formerly known as Sears Tower), and the Hancock Building; so whether you’re looking to snap some postcard-perfect shots or just take in the amazing architecture and natural beauty of Chicago from a different perspective, this is definitely the way to do it.
Seel also: best architecture boat tours in Chicago
Choose from luxury yachts, family-friendly ferries, or heart-racing speedboat rides; book your ticket in advance to save a few bucks, and enjoy the sail!
15 – Garfield Park Conservatory
An enchanting slice of nature in an otherwise chaotic metropolis, the Garfield Park Conservatory is a haven of tranquility in the heart of Chicago.
Boasting thousands of species of plants from all around the world, this award-winning conservatory is one of the largest indoor gardens in North America and makes for a peaceful and educational day out for visitors of all ages.
What’s more, entry is free 365 days per year so you can come as often as you like; just be sure to check the opening hours as they do vary depending on the season.
Hot tip: don’t miss the marvelous permanent glasswork by artist Dale Chihuly.
16 – Maggie Daley Park
Sandwiched in between Millennium Park (home of The Bean) and the Lake Michigan shoreline, Maggie Daley Park is a relatively recent addition to the Chicago tourist scene — but it hasn’t taken long for it to become a magnet for locals and visitors alike.
Opened in 2014, gentrifying the old three-level East Monroe Street Parking Garage, the park is all about fun for the whole family, with a whimsical play garden full of climbing towers, slides, swings, and splash zones, as well as the ice skating ribbon, sports fields, and plenty of picnic areas – not to mention some amazing views!
Whether you’re bringing your kids along or just want an excuse to act like one yourself, this sprawling 25-acre green space offers plenty of entertainment options no matter what time of year it is. And, best of all, admission is always free.
17 – Adler Planetarium
For an out-of-this-world experience, it’s time to head over to the Adler Planetarium.
The first planetarium in the Western Hemisphere (opening back in 1930) and one of Chicago’s most famous sights, this incredible museum is home to three full-size theaters where visitors can get a glimpse of what life would be like on Mars or learn about Jupiter, the moon and more through amazing high-tech displays and interactive exhibits.
There are also fascinating rotating exhibitions focusing on everything from telescopes to space travel (including the actual Gemini 12 space capsule); plus an observatory deck with beautiful views over Lake Michigan – all set within a striking Art Deco building designed by Ernest Grunsfeld Jr., which was declared an official National Historic Landmark back in 1987.
With so much going for it, as well as regular neighborhood skywatching events (check the events calendar), this interstellar attraction is one of the best places to visit in Chicago.
18 – Soldier Field
The locally beloved stomping ground of the Chicago Bears NFL team, Soldier Field delivers a roar and energy matched by few stadiums in the Midwest, regularly packing every seat in the house for home games.
But even when the Bears are on the road, this massive structure (the third-largest in the NFL) is worth a visit for its impressive architecture and unique history – after all, it’s been around for the better part of a century. Tours are available on non-game days, while a range of concerts dots the calendar too — or you can simply enjoy a walk around the perimeter and (thanks to its location at the southern end of Grant Park) take in some amazing views of downtown Chicago.
19 – Chicago Children’s Museum
A Navy Pier crowd favorite, the Chicago Children’s Museum is the perfect place to take your little ones for a day of fun peppered with a whole lot of learning.
With three floors of interactive exhibits designed specifically for children, this colorful museum provides hours of entertainment with a wide variety of hands-on exhibits that dive into the wonderful worlds of science, culture, construction, art, and more.
Best of all, admission is free for children under 17 (and affordable for everyone else), and free to Illinois residents every Tuesday from 2 pm onwards, so it’s a great place to take the whole family for a day of immersive creativity and learning without breaking the bank.
20 – Glessner House
Standing since 1887, the Glessner House is one of Chicago’s oldest and most beautiful homes, attracting visitors from all over the world with its exquisite architecture and fascinating history.
Designed by architect Henry Hobson Richardson (one of America’s first masters of the Romanesque Revival style) this iconic structure was once at the forefront of innovative home design, incorporating features like central heating and indoor plumbing (which were still pretty new ideas back in the day).
These days it serves as a museum open to the public, housing rotating exhibitions on everything from furniture design to decorative arts. DIfferent tours (focused on topics like architecture, history, or arts and crafts) are available daily, or you can simply admire it from the outside while enjoying a stroll around the Prairie Avenue Historic District.
21 – Loop district
In the heart of downtown Chicago, you will find The Loop – an area that was once a tangled maze of train tracks and elevated trains. Nowadays it’s a vibrant commercial district where many locals work, shop, dine out and hang out.
Its name comes from its circular shape – created by the “loop” made when trolleys traveled around the street block that encircled this central business district (the tracks have since been removed).
Attracting tourists like fish to water, The Loop is home to some of Chicago’s most famous buildings (including Willis Tower and the Chicago Board of Trade Building) as well as numerous theaters and museums (including the Chicago Cultural Center).
Take a stroll — or a guided walking or biking tour — around and you’ll uncover dozens of iconic sculptures on display along its streets, as well as some of the best donuts, pizza, architecture interiors, and shopping and dining in the city.
22 – Oz Park
Made famous for its whimsical statues of Scarecrow, Lion, Tinman, and Dorothy and Toto, Oz Park is a small (but charming) public park over in the Lincoln Park neighborhood on Chicago’s north side that blends the peace and quiet of nature with the childish wonder of one of the world’s most beloved stories.
Named for L. Frank Baum’s classic book The Wonderful Wizard of Oz, the underrated park features a range of fun attractions like a playground (called Dorothy’s Playlot), a lush Emerald Garden, tennis courts, basketball courts, and more. Best of all, it’s free to enter and explore!
And, during the balmy summer nights, grab a lawn chair for Movies in the Park!
23 – Baháʼí House of Worship
An architectural masterpiece, the Baháʼí House of Worship (also known as a “Lotus Temple”) is one of only seven Baha’i temples in the world and the only one located in North America.
The beautiful, lotus-shaped, nine-sided building dates back to the mid-1900s and has become iconic in its beauty, combining neoclassical symmetry, with Gothic, Renaissance dome, Romanesque and Islamic elements — all combining to make a structure that is both spiritual and stunning.
The temple is open to all, regardless of religious affiliation (or none), and visitors are welcome to come to explore the interior prayer hall, which features marble floors, fine woodwork, and beautiful stained-glass windows, as well as the large garden that offers plenty of space for visitors to stroll around, relax or meditate on life’s big questions.
24 – Congress Plaza Hotel
One of Chicago’s most iconic hotels and a piece of living history, The Congress Plaza Hotel on Michigan Avenue is a grand Beaux-Arts building dating back to 1893.
Over its near-130-year timeline, it’s hosted visitors, heads of state, and celebrities from near and far, dishing up wondrous views over both Downtown and Lake Michigan, with a prime spot opposite the Art Institute of Chicago, just minutes from Millennium Park.
Its history goes way beyond that though — the hotel has been labeled one of America’s most haunted hotels with ghost stories galore, including that of gangster Al Capone and his men who stayed here in the 1920s!
Learn all about the topsy-turvy tales of this longstanding landmark on a spine-tingling ghost and gangsters tour that dives into the dark side of Chicago’s history.
25 – Music Box Theatre
One of Chicago’s oldest and most beloved movie theaters, The Music Box Theatre on Southport Avenue in Chicago’s Lakeview district has been screening all kinds of indie and art-house films since 1929.
What began as a single-screen theater showing silent movies (and later “talkies”) quickly became known as one of the city’s most unique venues, thanks to its charming art deco facade and intimate seating that always guarantees a great view from any seat in the house.
These days, it’s still going strong with a busy schedule of new releases and cult classics, plus occasional live stage shows and events.
Check out what’s playing during your next visit to see if you can snag tickets to an old-school flick at this classic Chicago cinema!
26 – LEGOLAND Discovery Center
Adored by kids and parents alike, the Legoland Discovery Center is a highly-interactive indoor attraction in Chicago’s Woodfield Mall that brings all of Lego’s favorite toy brick creations to life!
Inside visitors will find everything from an awesome Miniland featuring replicas of some of America’s most famous landmarks made entirely out of Lego bricks (including a replica of the entire Windy City!), a 4D cinema, no less than 10 different hands-on play zones, a couple of rides, and a store chock-full of over 900 unique builds and souvenirs.
The center also hosts regular events like Master Builder Workshops and holiday celebrations, so be sure to check what’s happening during your visit before you go! And, since it’s located over in Schaumburg, it’s a good excuse to check out the nearly Ned Brown Preserve (Busse Woods) on the same day.
27 – Indiana Dunes National Park
For when you want to get out of the city and experience a little bit of nature, Indiana Dunes National Park is only an hour away from Chicago via car or train, straddling the southern shores of Lake Michigan in neighboring Indiana.
An adventurer’s heaven on earth, the sprawling park encompasses over 15,000 acres of dunes, beaches, grasslands, wetlands, prairies, and meandering rivers, and a whopping 50 miles worth of hiking trails — the most picturesque of which tackles dune formations that rise as high as 200 feet above sea level!
Hiking aside, visitors can swim at its many beaches (including some dog-friendly beaches), try horseback riding, cycle down the Calumet Trail, camp overnight, or just enjoy soaking up the immense beauty on offer here — it’s all about getting back to nature for a day and letting Mother Nature work her magic.
28 – Promontory Point at Burnham Park
One of the most iconic spots on Chicago’s South Side for a leisurely stroll, Promontory Point at Burnham Park is a narrow peninsula that juts out into Lake Michigan between 53rd and 57th Streets and offers sensational views of Downtown and the city’s famed skyline.
The 40-acre point has been popular with locals and visitors alike since it first opened in the 1930s and these days is home to lovely gardens, a couple of sculptures, plenty of local birds and wildlife, and a handful of benches where you can sit back and take in all the beauty on show.
29 – Museum of Science and Industry
One of the largest science museums in the world, Chicago’s Museum of Science and Industry is a sprawling complex that takes up the equivalent of an entire city block in the middle of Jackson Park, diving into fascinating exhibits on everything from aviation and outer space to WWII, natural disasters, dinosaurs, chemistry, and energy.
In addition to its over 35 permanent exhibits, the museum also hosts regular temporary exhibitions (just check the website to find out the flavor of the month), features an Omnimax theater, a carousel, and plenty of hands-on activities for kids (and adults
With myriad interactive elements, curious visitors can climb aboard a WWII German submarine, take a spin in a human-sized hamster wheel, navigate through a mirror maze
30 – United Center
Sports fans, listen up! Exuding a roar and an energy that can send shivers down your spine, Chicago is home to one of the most iconic and renowned sports arenas in the world: the United Center.
Home to not just the Chicago Bulls (of Michael Jordan fame) and Chicago Blackhawks (of the NHL), but also a whole range of other top-level events like concerts (think Iron Maiden; Elton John; Tyler, The Creator, and everyone in between) family shows, and more, United Center welcomes millions of guests through its doors every year.
With a capacity of close to 20,000 spectators, this arena — which, mind you, is officially the largest indoor arena in the country — really knows how to pack in the crowds for some unforgettable live action.
31 – Alfred Caldwell Lily Pool at Lincoln Park
A tranquil oasis in the heart of bustling Lincoln Park, Alfred Caldwell Lily Pool is a historic slice of nature and one of the most picturesque — and underrated — attractions in the city.
Designed by celebrated Prairie School architect Alfred Caldwell with roots going all the way back to 1889, the lily pool pays homage to the Midwest’s natural prairie landscape with its flowing curves and earthy hues, while offering visitors a chance to take a break from the go-go-go mentality of city life.
Open from early May until mid-November each year, this little slice of paradise welcomes locals and tourists alike for a relaxing stroll, a guided tour, or an enchanting and educational wildflower walk.
32 – Great Wolf Lodge Water Park Illinois
Perfect for energetic kids (and kids at heart); if you’re in the mood for some serious water park action, look no further than the Great Wolf Lodge.
Located over in Gurnee, Illinois (just a short drive from downtown Chicago), this massive water park resort is home to an impressive dozen towering slides (thrillseekers, make a beeline for the Double Whirlwind), a wave pool, lazy river, kiddie splash zones, and a whole lot more.
Not only will you find something for everyone here, but with its on-site restaurants, arcade games, live shows, mini-golf course, climbing walls, ropes course, pint-sized bowling alley, ever-popular Build-A-Bear workshop, and themed suites (we’re talking everything from log cabin-themed to cave-themed), there’s bounds of entertainment around every corner!
33 – Museum Of Contemporary Art
If you’re in the mood for some cutting-edge contemporary art, the Museum of Contemporary Art sells itself as one of the more intriguing places to visit in Chicago. Located in the trendy and vibrant neighborhood of River North, this museum has been showcasing boundary-pushing artwork since it opened its doors back in 1967.
Boasting an ever-changing roster of exhibitions (some permanent, others rotating), that cover paintings, sculptures, film, and photography, as well as a busy schedule of talks, performances, and educational programming geared towards all ages, MCA is always worth a visit if you want to see what’s new and exciting in the world of contemporary art (it is, after all, one of the biggest contemporary art venues on the planet).
Traveling in July or August? You’re in luck! Admission is free for everyone during the summer.
34 – Wrigley Field
A beloved American pastime, baseball is taken to a whole new level at Wrigley Field. Home of the Chicago Cubs (who recently overcame a 70+ year World Series drought), this stadium is one of the most iconic and hallowed venues in all of sport, not just baseball.
From its ivy-covered walls to the hand-turned scoreboard, there’s plenty of charm and character to be found at Wrigley. And, of course, there’s the history. Opened all the way back in 1914, this is one of America’s oldest ballparks still in use today.
If you’re a fan of baseball (or just want to experience some truly iconic Americana), be sure to plan a visit to Wrigley Field during your time in Chicago — or, take your experience to the next level with a 90-minute behind-the-scenes stadium tour that takes you into the Cubs’ dugout, the Bleachers, and the Press Box!
35 – Chicago Cultural Center
Home to a staggering variety of free art exhibits, performances, and educational programs (not to mention the occasional blockbuster traveling exhibition), the Chicago Cultural Center is one of the city’s most beloved and well-used attractions.
Located in the heart of downtown Chicago, this Beaux-Arts beauty was originally built back in 1897 as the city’s central library. However, fast forward to 1976 and it reopened as the Chicago Cultural Center we know and love today, with grand staircases, foreboding entrancement ways, coffered ceilings, and bronze-framed doors that make the building a piece of art in its own right — the Preston Bradley Hall and Tiffany glass dome, which contains some 30,000 pieces of glass, are shining examples.
Boasting an impressive five floors of exhibition space, there’s always something new to see at the Chicago Cultural Center — from contemporary art to historical artifacts, and several educational workshops to boot.
36 – Robie House
Tucked away off the beaten track in Hyde Park, on the University of Chicago campus, architecture buffs will drool over one of the most important examples of Prairie School architecture in the world; Frank Lloyd Wright’s Robie House is a must-see for fans of 20th-century design.
Commissioned by wealthy University of Chicago trustee and businessman Frederick C. Robie, this stunning home was designed by Wright in 1908 and completed in 1910.
Its clean lines and geometric shapes are an early example of Wright’s signature “Prairie Style” that would come to define his career — and it continues to be known today as the first uniquely American architectural style.
Now a National Historic Landmark, the Robie House is open to the public for tours (check out their website for more information on guided or self-guided tours). If you’re lucky, you might even catch one of their special events held throughout the year.
37 – DuSable Museum of African American History
Housed in a beautiful building on the eastern side of Washington Park — about 15 minutes drive south of Downtown Chicago — the DuSable Museum is one of the most important museums in the country devoted to African American history and culture.
Named after Jean Baptiste Point du Sable, widely considered to be the first non-indigenous settler to explore the area and as such the ‘Founder of Chicago’, this museum tells the story of Africans and African Americans from pre-colonial times to the present day.
The DuSable Museum is home to a wide variety of exhibits on everything from art and music to politics and civil rights, as well as an impressive research library containing tens of thousands of volumes, and a regular even calendar that features concerts, films, kid-friendly events, and debates.
Take a stroll around the peaceful outdoor sculpture garden which displays works by some of today’s leading African American artists, and make sure to visit the museum’s gift shop for some unique souvenirs and books to further your learning.
38 – Chicago Architecture Center
If you’re at all interested in architecture, or in just taking a stroll around one of the most beautiful cities on Earth, then the Chicago Architecture Center is a must-visit. Located in the heart of Downtown Chicago, this center offers free tours (both guided and self-guided) of some of the city’s most iconic buildings, as well as lectures, exhibitions, and family activities.
The CAC’s main attraction is their 90-minute walking tour that takes visitors through downtown Chicago’s Loop district to see some of the city’s best-known (and sometimes controversial) buildings up close. From grandiose skyscrapers like The Willis Tower and John Hancock Center to classical masterpieces like Louis Sullivan’s Carson Pirie Scott store, there’s something for everyone to marvel at.
All up, the CAC offers some 85 tours of the city’s neighborhoods, including boat tours along the Chicago River (which come highly recommended!), and even a tour of Frank Lloyd Wright’s home and studio in Oak Park. Simply check out their website for more information on what’s on offer.
39 – Tribune Tower
No trip to Chicago is complete without a visit to the Tribune Tower, one of the city’s most iconic and best-loved buildings. Located on Michigan Avenue, smack-bang in the center of the Loop district, this neo-gothic tower was completed in 1925 and has been home to the Chicago Tribune newspaper ever since.
Besides boasting a fascinating century’s worth of history, it’s the building’s facade that gleans the most interest: the exterior of the building is covered in over 150 different types of famous marble, limestone, and granite building fragments from all over the world — we’re talkin’ pieces of the Parthenon, the Notre Dame cathedral, the White House, and even the Berlin Wall.
40 – Illinois Beach State Park
Located in northern Lake County (about an hour’s drive north of Chicago, halfway to Milwaukee), the Illinois Beach State Park is a nature lover’s paradise.
With its sprawling grassy dunes, lakeside forests, and stunning sandy beaches, it’s no wonder over 2.5 million people flock to this park every year — although, at a whopping 4,160 acres, it never feels even remotely crowded.
Full of family-friendly activities to escape the city and soak in the best of Mother Nature, the park offers plenty to keep you occupied during your stay: go hiking along dozens of miles worth of trails and enjoy the 650+ species of plants that cover the area;
Keep your eyes peeled for rare and majestic birds flying above the North Unit (the park is split into two units); fish for salmon or trout in Sand Lake; take a dip in Lake Michigan — swimming and sunbathing are popular pastimes here — or simply grab yourself a picnic table and soak up all that fresh air!
41 – Chicago Theatre
Making for a splendid evening out on the town, a night at the Chicago Theatre is always a good idea for traveling couples looking for a slice of romance or film buffs looking to dive into a slice of American cinematic history.
This grand old movie palace, located on North State Street in the Loop district and able to seat 3,600 people, has been entertaining theater-goers since 1921 — it was the first lavish movie palace in the nation, setting the standard for all that followed, and today remains one of the most popular venues in the city for live performances.
The theatre’s facade is an impressive sight, towering seven stories tall with a postcard-worthy neon sign juxtaposing Romanesque Revival details, and inside you’ll find a beautifully restored auditorium with gilded ceilings, marble flooring, and luxury touches galore.
Check the calendar, choose from comedy nights, live music shows, film screenings, or Broadway shows (or even a behind-the-scenes theater tour), and get ready to be entertained!
42 – National Museum of Mexican Art
Portraying the rich culture, history, and artistry of Mexican heritage in America (and beyond), the National Museum of Mexican Art is definitely worth a visit while you’re in Chicago if you’re looking to expand your cultural horizons.
The museum’s collection spans over 35 centuries — with archeological finds dating back to ancient Mesoamerica covering everything from traditional crafts and jewelry to fine art painted by some of Mexico’s most renowned artists and modern takes on photography and pop-art — making it one of the largest collections of its kind in the US.
You can also get more out of your visit by checking out their calendar for upcoming events: workshops are regularly available (think writing classes or guest speakers), as well as performances and expert-led tours.
Plus, thanks to its location in Harrison Park in the Pilsen neighborhood, there’s plenty of space to take a stroll and stretch the legs afterward.
43 – Frank Lloyd Wright Home and Studio
When it comes to architectural wonders, Frank Lloyd Wright is a name you can’t ignore. And here in Chicago, you can visit his original home and office — now officially known as The Home & Studio of Frank Lloyd Wright — which was built in 1889 by the famed architect himself, serving as the place where he’d pen over 150 different designs that would eventually manifest into a legacy of world-famous buildings.
The studio has been meticulously restored to its 1890s appearance and today offers guided tours that highlight pieces of furniture and dive into the life and works of the iconic architect.
Craving more Frank Lloyd Wright? See inside the architectural gem that is the Robie House in Hyde Park, or visit the Unity Temple in Oak Park to see another of his works — both spots are listed on many a list of the quintessential places to visit in Chicago.
44 – Waterfall Glen Forest Preserve
Located just southwest of the city limits in Darien, about 25 minutes inland from Chicago, Waterfall Glen Forest Preserve is a vast tract of land covering over 2000 acres (and featuring 11 miles of trails) that’s ideal for hiking, biking, horseback riding, and cross-country skiing, or simply basking in the fresh and quiet air.
Families and adventurers alike can easily spend an entire day out here exploring all it has to offer: there are wooded areas and open meadows, wildflower fields to roam through, rock formations, and over 300 species of wildlife roaming around to admire — along with the main attraction that is the waterfall (read: a dam), of course.
For a wonderful viewpoint, check out the Sawmill Creek bluff overlook, and for something unexpected, make your way to the model-airplane field at Mile 3 on the loop trail.
45 – Orchestra Hall
Home to the highly esteemed Chicago Symphony Orchestra, Orchestra Hall is an architectural gem in itself. Built in 1904 and designed with the help of architect Daniel Burnham (who was also responsible for Manhattan’s Flatiron Building), it’s one of those buildings that feels like you’re stepping into a movie set.
Curious travelers can take a guided tour to learn more about its history — from construction back when Symphony Center first opened up as Orchestra Hall through to modern times where it now hosts over 300 concerts each year — or simply sit down and enjoy some world-class music within the walls of a National Historic Landmark; tickets are available online and at the box office, just be sure to book in advance to avoid missing out).
46 – Cantigny Park
Calm and green and always free to visit, Cantigny Park is a 500-acre oasis located in Wheaton, about 40 minutes island from downtown Chicago, that’s perfect for a relaxing day out of the city.
The park was once the estate of Colonel Robert R. McCormick (the founder and publisher of the Chicago Tribune), and it’s now open to the public with plenty to keep visitors entertained: from gardens and nature trails to picnic areas and playgrounds, there’s something for everyone here.
Culture vultures and history buffs flock here too, for good reason. Cantigny is home to The Robert R. McCormick Museum, which dives into the life and work of the media mogul; and The First Division Museum, which immerses visitors in the sights, sounds, and stories of the military unit.
47 – Peggy Notebaert Nature Museum
Charming locals and tourists alike with its interactive exhibits that explore all aspects of nature — from animals and plants to insects (the Judy Istock Butterfly Haven is by far one of Chicago’s cutest attractions) — since 1999, the Peggy Notebaert Nature Museum is a must-visit for anyone with an appreciation for the natural world.
The museum also offers up educational programs and events, like animal feedings, the regular Critter Connection where you can meet and greet snakes and turtles, yoga in the Butterfly Haven, birdwatching excursions, and a host more, so keep an eye out on their website to see what’s happening during your visit.
Make sure to take a stroll on the outdoor walkways to observe the local wildlife doing its thing, and learn about the importance of climate change at the fascinating Weather to Climate exhibit.
48 – The Green Mill
A hidden gem beloved by locals and jazz aficionados the world over (and frequented by Al Capone and his goonies way back yonder), The Green Mill is a Chicago institution that’s managed to keep its Prohibition-era speakeasy charm intact over a century later.
First opened all the way back in 1907, it was originally a venue for vaudeville and variety shows (Green Mill is actually a nod to the famous Moulin Rouge in Paris, which translates to the ‘Red Mill’) before becoming one of the most popular jazz clubs in America, even hosting performances by legends like Louis Armstrong, Billie Holiday and Charlie Parker along the way.
While nowadays it’s not quite as rowdy as it once was in the Capone era, the club still offers up toe-tapping live music every night of the week and some of the best cocktails around; just be sure to arrive early It gets busy so get there early as there are no reservations.
With plenty to see in do in the neighboring Uptown streets, including restaurants and shopping galore, The Green Mill is a great spot to end an evening after exploring the neighborhood.
49 – Illinois Holocaust Museum & Education Center
A somber and eye-opening look at one of the darkest moments in human history, the Illinois Holocaust Museum & Education Center is a confronting but important experience for anyone making a trip to the Chicago area.
Dedicated to Holocaust remembrance and education, the Museum features exhibits that tell the personal stories of survivors, provides reflecting rooms and powerful tributes, and showcases a range of artifacts from WWII, concentration camps, and ghettos.
The museum also offers educational programs on genocide awareness, and historian-led tours to get the most out of your trip.
What sets this museum apart from other Holocaust museums is its new virtual reality exhibition, The Journey Back. Using VR technology, visitors are taken on walks through concentration camps alongside Holocaust Survivors, hearing their captivating memories and stories first-hand.
50 – Morton Arboretum
An outdoor wonderland full of the most beautiful trees and flowers, the Morton Arboretum is undeniably one of the best places to visit in Chicago not just for nature-lovers, but for every type of visitor, entertaining locals and tourists alike for over 100 years.
With 16 miles of hiking trails that twist and turn their way through more than 1,700 acres, plus stunning sculpture-filled gardens, a maze garden, tourist trolley, library, and a herbarium, there’s plenty of fun to be had at this lush oasis just outside Chicago (about 25 minutes outside, to be exact).
Hot tip: if visiting during the winter, be sure to check out the magical illumination show, where towering trees are lit up with 150 colorful lanterns and colorful projections, providing a beautiful splash of color on the usually snowy-white backdrop, made all the more memorable by roasting marshmallows and crackling fires along the way.
Want a travel hack? Grab a city tourist pass!
We are undoubtedly spoiled for choice in this midwestern metropolis. Thankfully, to take the confusion and hassle out of selecting and choosing where to start, how to get around, and which destinations to prioritize, the folks behind the City Pass and Go Chicago Explorer Pass have already done all the hard work for us.
Tailored specifically to those excited tourists who visit Chicago every year in search of hearty deep-dish pizza and brilliant museums (and all the other goodies we’ve mentioned) these passes offer great value-for-money deals and allow you to see and experience as much, or as little of the city as you please.
With a bounty of options to choose from for every budget, interest, and timeframe, these passes are a great way to see the best of Chicago’s attractions — like the Field Museum, Skydeck Chicago, and Hop-on-Hop-off bus – and save a few bucks along the way. In fact, you can save up to 44% of the regular costs if you were exploring solo!
Looking for a hotel?
Hundreds of hotels of all shapes, sizes, and price tags line the streets of Chicago, so rest assured that there’s something for every style (luxury VS basic) and every location (right in the city center, or a bit further out).
Craving a little luxury? The Waldorf Astoria oozes elegance, the Gwen on the Magnificent Miles comes with complimentary shoe shines and clothes pressing (which should say just enough about the opulence of this place); the Ritz-Carlton and the Langham boast fine reputations that precede them, and the 5-star Peninsula Hotel, which welcomes celebrities on the regular, is often voted the #1 Hotel in Chicago.
For excellent yet slightly more affordable options, any of the Sofitel, Marriott, or Radisson are popular choices, while if you can snag it at a bargain rate, the Drake dishes up splendid lakeside views.
Hot tip: check online to find the best deals on hotels all around Chicago — from budget-friendly motels to luxurious five-star resorts. With so many options to choose from, it’s easy to find something that suits your travel needs and budget. And, compared to walk-in prices, you could save hundreds.
Save yourself hassle: book an airport transfer
Is there anything worse than arriving at an airport and having to wait in lengthy queues for a taxi or public transport? Especially when you’re tired after your flight, not sure where you’re going, and don’t know the local lay of the land.
Thankfully, with so many tourists flocking to Chicago every year, there are lots of companies who offer pre-booked transfers from both of the city’s airports – O’Hare and Midway – to your hotel or accommodation. This way, you can avoid long queues, get straight to your destination without any fuss, and start exploring as soon as possible. Plus, if traveling as a group, it’s often cheaper than the total cost of transport tickets (and far more comfortable)!
And that’s a wrap! We hope this article has given you a little taste of the best places to visit in Chicago! So whether you’re visiting in the summer, winter, or any time at all, you can expect a warm welcome from locals and tourists alike.
Have any questions about the different attractions? Want more recommendations on where to eat, drink, or stay? Or perhaps you’re looking for some tips on how to get around the city (and which neighborhoods are worth exploring)? Let us know in the comments below! As always, happy travels!