Chicago Seasonal Stroll Walking Tour of Holiday Attractions
Overview
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 spark your holiday spirit with fun facts, cultural insights, & the very best seasonal décor—like the surprising fact that Rudolph the Red-Nosed Reindeer was created in Chicago! Along the way, you’ll marvel at the iconic Christmas window displays of the original Marshall Field’s store, admire Chicago’s official Christmas tree, Mag Mile lights, and take in the festive Millennium Park ice skating rink. You’ll even enjoy VIP access—no waiting in line—to the legendary Christkindlmarket, the city’s beloved German holiday market. If you’re searching for Things to do in Chicago during the holidays, this experience is a perfect fit. Note: This is a walking tour only.
What's Included
- 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.
- Marvel at Macy’s iconic holiday windows—sparkling scenes that capture pure Christmas joy.
- Join a lively local guide who brings Chicago’s holiday spirit to life with every story.
- Hotel pickup and drop-off
- This is purely a walking tour, no food or drink offered on this tour
- Optional gratuity: $6 per person (or more) suggested guide gratuity (via Cash, Venmo and PayPal)
Meeting Location
150 North Dearborn Street
Chicago, IL 60601, USA
Detailed check-in instructions, including the exact address, are provided with your booking confirmation.
400-410 Michigan Avenue
Chicago, IL 60611, USA
This is the End point of your Chicago Seasonal Walking Tour.
What To Expect
Book Online
Safe & secure Easy breezy Hassle‑free
Christkindlemarket
20 minutes Admission Ticket Free
Chicago Christmas Tree
10 minutes Admission Ticket Free
Millennium Park Ice Rink
5 minutes Admission Ticket Free
Cloud Gate
5 minutes Admission Ticket Free
Macy's on State Street
10 minutes Admission Ticket Free
The Magnificent Mile
5 minutes Admission Ticket Free
Millennium Park
30 minutes Admission Ticket Free
Michigan Avenue Bridge
5 minutes Admission Ticket Free
Daley Bicentennial Plaza
10 minutes Admission Ticket Free
Jay Pritzker Pavilion
5 minutes Admission Ticket Free
The Chicago Theatre
5 minutes Admission Ticket Free
Palmer House Hilton Historic Lobby
5 minutes Admission Ticket Free
State Street
5 minutes Admission Ticket Free
Additional Info
- Confirmation is instant and will be received at time of booking
- Wheelchair accessible
- Transportation options are wheelchair accessible
- All areas and surfaces are wheelchair accessible
- Service animals allowed
- Public transportation options are available nearby
- Suitable for all physical fitness levels
- Infants and small children can ride in a pram or stroller
- 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
- [BRAND] 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.
- This tour/activity will have a maximum of 15 travelers
Frequently Asked Questions (8)
Q: What is the cancellation policy for the Chicago Seasonal Stroll Walking Tour of Holiday Attractions?
Cancellation Policy
Still have questions?
We're here to help.
Activity code: C-3332P22
Traveler Photos
Reviews
Average 5.00 out of 5 stars based on 5 traveler reviews collected by Cool Shore Excursions and partner sites such as Cool Destinations and TripAdvisor
Additional Info
Similar Tours & Activities
Discover the elegance and beauty of Hanfu, the traditional clothing of ancient China, in this one-of-a-kind cultural experience here at our Chinatown Visitor Center! Step...
$20
This isn’t just a ghost tour, it’s a story-driven walk through one of Chicago’s most haunted landscapes, where real history and local legend collide. Unlike...
$30
The year is 1375, and a devastating drought grips China. The Emperor sends you, his Imperial Advisor, to find the four Dragon Kings, rulers of...
$8
Chicago Scavenger Hunt Adventure
Turn Chicago into a giant game board with this fun scavenger hunt adventure! This challenge combines the excitement of the Amazing Race with a 3-hour...
$49
Discover the elegance and beauty of Hanfu, the traditional clothing of ancient China, in this one-of-a-kind cultural experience here at our Chinatown Visitor Center! Step...
$20
This isn’t just a ghost tour, it’s a story-driven walk through one of Chicago’s most haunted landscapes, where real history and local legend collide. Unlike...
$30
The year is 1375, and a devastating drought grips China. The Emperor sends you, his Imperial Advisor, to find the four Dragon Kings, rulers of...
$8
Turn Chicago into a giant game board with this fun scavenger hunt adventure! This challenge combines the excitement of the Amazing Race with a 3-hour...
$49
Travelers Who Bought This Tour Also Bought
Chicago River 90 Minute Architecture Tour
Be inspired by the captivating, visual art that is Chicago’s legendary architecture, and the exceptional architects who created this ever-changing, dynamic legacy for all to...
$45
Chicago Lake and River Architecture Tour
An authentic Chicago tradition since 1935, this is the tour that started it all. This unique excursion tells the story of more than 200 years...
$45
Chicago Crime and Mob Bus Tour
Escape into Chicago's underworld on a crime and mob tour with stops on-and-off the luxury, climate-controlled bus. Explore historic crime scenes with great photo opportunities....
$49
Experience Chicago's legendary architecture and the exceptional architects who created this ever-changing legacy for all to admire. This family-friendly introduction to the Windy City's rich...
$28
Be inspired by the captivating, visual art that is Chicago’s legendary architecture, and the exceptional architects who created this ever-changing, dynamic legacy for all to...
$45
An authentic Chicago tradition since 1935, this is the tour that started it all. This unique excursion tells the story of more than 200 years...
$45
Escape into Chicago's underworld on a crime and mob tour with stops on-and-off the luxury, climate-controlled bus. Explore historic crime scenes with great photo opportunities....
$49
Experience Chicago's legendary architecture and the exceptional architects who created this ever-changing legacy for all to admire. This family-friendly introduction to the Windy City's rich...
$28
Frequently Asked Questions (8)
The answers provided below were previously given in response to questions from Cool Shore Excursions customers.
Filter by:
- For a full refund, you must cancel at least 24 hours before the tour start time.
- If you cancel less than 24 hours before the tour start time, the amount you paid will not be refunded.
- Any changes made less than 24 hours before the tour start time will not be accepted.
- Cut-off times are based on the tour local time (CST).
- This tour requires a minimum number of travelers. If it’s canceled because the minimum isn’t met, you’ll be offered a different date/experience or a full refund.
- 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.
- Marvel at Macy’s iconic holiday windows—sparkling scenes that capture pure Christmas joy.
- Join a lively local guide who brings Chicago’s holiday spirit to life with every story.
- Hotel pickup and drop-off.
- This is purely a walking tour, no food or drink offered on this tour.
- Optional gratuity: $6 per person (or more) suggested guide gratuity (via Cash, Venmo and PayPal).
This tour requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.
Apr 2025There is no minimum age for this tour, so bring your wee one along for an adventure. This tour requires at least one adult to accompany children..
Apr 2025If a date or time is not listed on the calendar, it’s sold out or unavailable for another reason. Support cannot assist further if a date or time is not on the calendar.
If you find a date and time that works for you, book it NOW because things always sell out at this time of year.
Apr 2025Accessibility information for the Chicago Seasonal Stroll Walking Tour of Holiday Attractions is as follows:
- Wheelchair accessible
- Transportation options are wheelchair accessible
- All areas and surfaces are wheelchair accessible
- Service animals allowed
- Public transportation options are available nearby
- Suitable for all physical fitness levels
Detailed check-in instructions – including meeting point address, Google map, and parking information – for Chicago Seasonal Stroll Walking Tour of Holiday Attractions will be included in your confirmation email from Cool Shore Excursions. Please be sure to double and triple check your email address is correct at checkout so this important email makes its way to you!
Mar 2024Once your refund is processed, it usually shows on your card statement within 5–10 business days. The exact timing depends on your bank or card issuer.
Want it sooner? When you cancel, choose Receive a refund to my wallet instead. The credit is in your Wallet straight away and is applied automatically at checkout on your next booking when you’re signed in with the same email. You can see your balance any time in My Wallet.
If you paid part of your booking with Wallet credit, that part always goes back to your Wallet. Trip protection isn’t refundable.
Oct 2026What's Included
- 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.
- Marvel at Macy’s iconic holiday windows—sparkling scenes that capture pure Christmas joy.
- Join a lively local guide who brings Chicago’s holiday spirit to life with every story.
- Hotel pickup and drop-off
- This is purely a walking tour, no food or drink offered on this tour
- Optional gratuity: $6 per person (or more) suggested guide gratuity (via Cash, Venmo and PayPal)
Additional Info
- Confirmation is instant and will be received at time of booking
- Wheelchair accessible
- Transportation options are wheelchair accessible
- All areas and surfaces are wheelchair accessible
- Service animals allowed
- Public transportation options are available nearby
- Suitable for all physical fitness levels
- Infants and small children can ride in a pram or stroller
- 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.
- This tour/activity will have a maximum of 15 travelers
