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Chicago Tours

Discover 705 tours and activities in Chicago

Chicago Sightseeing Tours

Chicago Food Tours & Experiences

Chicago Private Tours

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The 10 Best Chicago Tours

1
Chicago Architecture River Cruise

Cruise along the Chicago River and admire the architectural highlights of this designer city from the comfort of an open-top boat. These Chicago tours are great for first-time visitors who want to get their bearings and see the sights from a unique angle.

Watch as the skyline drifts by, with over 40 famous landmarks to tick off including the John Hancock Building, the Navy Pier, and the East Bank Club. You’ll explore the three different river branches, with photo opportunities near the Willis Tower and the old Post Office building being highlights of the trip.

2
Gangsters and Ghosts Tour in Chicago

Walking tours are a fun way to discover the real Chicago, especially when they have a theme. These gangster and crime excursions reveal a darker side to the city, where mystery lurks around every corner.

You’ll see the historic neighborhoods from the perspective of mob bosses and ghouls as your guide regales you with entertaining tales on these fun Chicago tours. Be transported to the roaring 20s when bootleggers, speakeasies, and notorious characters like Al Capone were the talk of the town. Watch out for spooky goings-on as you explore haunted sites like Congress Hotel and the ominously named Death Alley.

3
Willis Tower Skydeck Chicago

Steady your nerves as you edge out on the glass-paneled balcony on the 103rd floor of the Willis Tower. This is one of the tallest buildings in the world, so you know the views are going to be epic. You’ll feel like you’re floating in the sky with the city sprawling out toward the horizon down below.

The Skydeck observation platform is one of the best places for panoramic views of the Windy City, with interactive displays taking you on a journey through Chicago’s intriguing history. Come at sunset to see the city blushed with color.

4
Underground Donut Tour in Chicago

Looking for unusual Chicago tours? Then munch your way through some of the city’s most coveted confectionery on a delectable dessert adventure in the heart of town. On this walking tour with a difference, you’ll be popping into a selection of Chicago’s finest donut shops to get your taste buds working in overdrive.

Whether you have a sweet tooth to satisfy or are just plain curious, the flavors on offer will be sure to lure you in. Whiskey salted caramel or toasted cinnamon apple anyone? The tempting treats can be cream-filled or glazed, with rainbow-colored sprinkles for added glamor.

5
Chicago Bike Tours

Exploring the city by bike is a great way to see the major landmarks in a short space of time. You’ll pedal through the lakefront neighborhoods as well as off-the-beaten-track spots in Chicago’s West Side. Highlights include riding by the Gold Coast mansions, Lincoln Park Zoo, and the original Playboy pad.

To ramp the excitement up a notch you can combine bike tours in Chicago with food tasting to keep your energy levels high! You’ll stop for burgers and beer in the historic Fulton Market district, tuck into tacos from street stalls, and try chocolate in the hippie Old Town.

6
Lake Michigan Sightseeing Cruise

Of all the Chicago tours on offer, this is a must for first-time visitors. Taking a boat tour across this vast lake is a relaxing way to see some of the sights, with commentary to give you an insight into the city’s diverse history.

Relax in your seat as you cruise along with the Chicago skyline gliding by outside. You’ll be able to spot some of the major landmarks from afar. Lunch and dinner sailings are available for those who want to explore in style or opt for a private charter or a sunset trip for a more luxurious experience.

7
Chicago 360 Observation Decks Tour

See the city from above with a visit to one of the best viewing platforms in Chicago. Hidden away on the 94thfloor of the John Hancock Center, the 360 Observation Deck gives you unrivaled panoramas over the famous skyline, framed by the glistening lake down below.

On a clear day, you’ll be able to see the neighboring states of Michigan, Illinois, Wisconsin, and Indiana from the lofty 1,030-foot deck. Venture outside onto the hair-raising tilting platform (TILT) for views over Michigan Avenue before watching the sun go down with a drink at the bar.

8
Navy Pier

Navy Pier is the city’s most iconic lakefront location, with world-renowned restaurants, boat tours, and shopping all in one place. This former freight dock has been developed into a glamorous waterside venue, with a funfair and stunning Lake Michigan views.

It’s a popular destination for walking tours in Chicago, as well as the jumping-off point for cruises. If you plan on spending time here, consider buying the Explorer Pass which gives you access to all the attractions, plus entry to several other sites across the city. Don’t leave without taking a ride on the Navy Pier Centennial Wheel.

9
The Loop Food Tour in Chicago

Dive into Chicago’s scrumptious foodie scene on one of these finger-licking excursions. You’ll follow your guide around the “Loop”, taking in hidden gems and listening to tales from the past that bring the city streets to life.

These Chicago tours let you tuck into the best of the city’s cuisine, from the famous deep-dish pizzas to moreish Italian beef sandwiches. Hot dogs with seven toppings and drinks at secret bars that survived the Prohibition are also on the menu. Wine tours and tastings are available for connoisseurs of the grape, while cooking classes are perfect for those who want to get hands-on.

10
Lakefront Segway Tour in Chicago

Segway tours in Chicago are a fun way to roll around town, taking in some of the major sights as well as exploring away from the crowds. If you haven’t done it before, don’t worry. Your expert guide will show you some tricks and you’ll soon be balancing like an old-timer.

Chicago is a huge city, so using wheels rather than feet will mean you’ll get to cover a lot more ground. You’ll glide along the lakefront, before riding through the historic downtown area for a contrasting vibe. There will be plenty of photo stops so don’t forget to take your camera.

Planning your visit to Chicago

About Chicago

Affectionately known as the “Windy City”, Chicago sits in America’s MidWest, right on the shores of the great Lake Michigan. It’s one of the most popular city destinations in the United States, thanks to its incredible range of attractions, art galleries, and 20th-century urban architecture. Everyone from Picasso to Frank Lloyd Wright has left their mark on this sprawling metropolis, and it’s this diversity that makes the city so appealing.

History lovers, art fans, and foodies will love exploring the museums and markets on Chicago tours, while outdoor enthusiasts can enjoy lake cruises or stroll on the beautiful waterfront beaches.

Good to know before arriving

If you’re staying for a few days, it’s worth buying the Chicago City Pass or the Chicago Explorer Pass which will give you access to multiple attractions. A good way to start is with a hop-on hop-off bus tour, to help get your bearings without the hassle of having to figure out transport. We recommend booking a hotel in the center of town so you’re not far from the main sights.

It’s advisable to wear comfortable walking shoes during tours in Chicago as you’ll probably be spending a lot of time strolling the streets. Take some warm layers too as temperatures can fluctuate, even in summer.

Places and experiences that cannot be missed

Lake Michigan and the observation towers are must-sees during your visit, but there are plenty of other attractions beyond the main Chicago tours. Street art excursions are all the rage, while the Museum of Natural History and the Art Institute of Chicago are also worthy contenders.

Spend the evening watching the famous Blue Man Show or take the kids to Legoland Discovery for some serious outdoor fun. If you’re looking for free things to do, take a tour of the beautiful Chicago Cultural Center, ramble along the Lakefront Trail, or visit Clark House Museum - the oldest dwelling in town.

Looking for more inspiration?

Read our blog article about the best things to do in Chicago.
See all Chicago tours