Chicago Seasonal Stroll Walking Tour of Holiday Attractions

5.0

based on 5 reviews

| Chicago, United States

Features

Free Cancellation

For a full refund, cancel at least 24 hours before the scheduled departure time.

Instant ticket delivery

Mobile Ticket

Pickup available

Duration

2 hours

Wheelchair accessible

Audio guide

Live guide

Walk beneath millions of glittering lights as the Magnificent Mile glows for the season.
Skip the Lines—enjoy festive, VIP front-of-line access to Christkindlmarket’s holiday magic.
Stroll through Millennium Park as it sparkles with lights and joyful holiday energy.
Watch skaters glide under the skyline as Millennium Park transforms into a holiday wonder.
Experience State Street’s festive shops bursting with lights, décor, and holiday cheer.
See Chicago’s soaring Christmas tree glowing with festive lights—pure holiday magic.
See the Wrigley Building glow with festive lights—an elegant icon shining bright for Christmas.
Join a lively local guide who brings Chicago’s holiday spirit to life with every story.
Marvel at Macy’s iconic holiday windows—sparkling scenes that capture pure Christmas joy.

Optional gratuity: $6 per person (or more) suggested guide gratuity (via Cash, Venmo and PayPal)
Hotel pickup and drop-off
This is purely a walking tour, no food or drink offered on this tour

Mobile or paper ticket accepted
Service animals allowed
Public transportation options are available nearby
Infants and small children can ride in a pram or stroller
All areas and surfaces are wheelchair accessible
Transportation options are wheelchair accessible
Wheelchair accessible
Suitable for all physical fitness levels
All of our walking tours at the present moment do allow for ADA compliant and wheelchair accessible.
Operates in all weather conditions, please dress appropriately
TripAdvisor rated Bobby’s Bike Hike its highest-level Traveler’s Choice Award each year since 2002.
Minimum numbers apply. There is a possibility of cancellation after confirmation if there are not enough guests to meet requirements. In the event of this occurring, you will be offered an alternative or full refund.
Our groups have exclusive VIP access to locations we visit, including VIP access to Christkindlmarket.

There’s nothing more magical than Christmas in Chicago, & this 2hr guided Chicago Walking Tour takes you straight into the heart of it. Journey through the Chicago Loop, Millennium Park, & the Magnificent Mile with an internationally recognized tour company proudly headquartered right here in Chicago. Our entertaining guides will...

Duration 2 Hours
Group Tour
Max 15 people in the group

1
Christkindlemarket
Skip the long lines and get VIP entry into Christkindlemarket. Experience the magic of Christmas in Chicago Christmas as our Chicago Walking Tour guides you through the heart of the Christkindlmarket Chicago — one of the most beloved Things to do at Christmas in Chicago. Wander past glowing wooden stalls,...
- Duration 20 Minutes•
- No Admission Ticket Required•
- Local Guide Included
2
Chicago Loop
Marvel at one of the most iconic Things to do at Christmas in Chicago as our Chicago Walking Tour leads you to the dazzling Chicago Christmas Tree, glowing proudly in Millennium Park. This towering symbol of Christmas in Chicago Christmas shines with thousands of twinkling lights, handcrafted ornaments, and a...
- Duration 10 Minutes•
- No Admission Ticket Required

Michigan Avenue

Discover one of the most joyful Things to do at Christmas in Chicago as our Chicago Walking Tour brings you to the Millennium Park Ice Rink, sparkling with festive lights during Christmas in Chicago. Skaters glide beneath the skyline, music floats through the crisp air, and the entire scene captures...

Duration 5 Minutes•
No Admission Ticket Required

Cloud Gate

Experience one of the most iconic Things to do at Christmas in Chicago as our Chicago Walking Tour leads you to Cloud Gate—“The Bean”—shimmering beneath the winter lights. During Christmas in Chicago, this mirrored monument becomes a festive masterpiece, reflecting the skyline, twinkling decorations, and joyful crowds celebrating the Holidays....

Duration 5 Minutes•
No Admission Ticket Required

Macy's on State Street

Step into one of the most beloved Things to do at Christmas in Chicago as our Chicago Walking Tour brings you to the enchanting Macy’s on State Street Holiday Display. During Christmas in Chicago, the windows come alive with handcrafted scenes, nostalgic animations, and storybook artistry that has captivated Chicagoans...

Duration 10 Minutes•
No Admission Ticket Required

The Magnificent Mile

Witness one of the most dazzling Things to do at Christmas in Chicago as our Chicago Walking Tour guides you beneath the shimmering Magnificent Mile Lights. During Christmas in Chicago, this famous stretch glows with millions of twinkling bulbs draped across trees and towering storefronts, turning Michigan Avenue into a...

Duration 5 Minutes•
No Admission Ticket Required

Millennium Park

Experience one of the most iconic Things to do at Christmas in Chicago as our Chicago Walking Tour guides you through the festive heart of Millennium Park. During Christmas in Chicago, the park transforms into a glowing winter wonderland filled with shimmering lights, holiday art installations, and joyful crowds celebrating...

Duration 30 Minutes•
No Admission Ticket Required

Michigan Avenue Bridge

Take in one of the most enchanting Things to do at Christmas in Chicago as our Chicago Walking Tour brings you onto the historic Michigan Avenue Bridge, glowing with festive lights during Christmas in Chicago. From this iconic spot, the riverfront sparkles with reflections of holiday décor, towering trees, and...

Duration 5 Minutes•
No Admission Ticket Required

Daley Bicentennial Plaza

Discover a quieter gem among the Things to do at Christmas in Chicago as our Chicago Walking Tour leads you through Daley Bicentennial Plaza, where peaceful pathways and skyline views take on a warm glow during Christmas in Chicago. This serene corner of Grant Park becomes a winter hideaway filled...

Duration 10 Minutes•
No Admission Ticket Required

Jay Pritzker Pavilion

Experience a cultural highlight of the season as our Chicago Walking Tour brings you to the Jay Pritzker Pavilion, one of the most breathtaking Things to do at Christmas in Chicago. During Christmas in Chicago, Gehry’s sweeping steel ribbons shimmer with festive reflections, creating a dramatic winter backdrop unlike anything...

Duration 5 Minutes•
No Admission Ticket Required

The Chicago Theatre

Experience one of the most photogenic Things to do at Christmas in Chicago as our Chicago Walking Tour brings you to the legendary Chicago Theatre marquee, glowing brilliantly during Christmas in Chicago. Its neon lights shine even brighter against the crisp winter air, creating a cinematic holiday moment you can’t...

Duration 5 Minutes•
Admission Ticket Not Included

Palmer House Hilton Historic Lobby

Step inside one of the grandest Things to do at Christmas in Chicago as our Chicago Walking Tour brings you into the richly decorated lobby of the historic Palmer House. During Christmas in Chicago, this legendary hotel transforms into a glowing holiday escape filled with sparkling garlands, towering wreaths, and...

Duration 5 Minutes•
No Admission Ticket Required

State Street

Experience one of the most festive Things to do at Christmas in Chicago as our Chicago Walking Tour guides you through State Street Holiday Shopping, where the storefronts glow with dazzling décor during Christmas in Chicago. This legendary shopping district comes alive with sparkling lights, nostalgic displays, and the joyful...