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Chicago Seasonal Stroll Walking Tour of Holiday Attractions

5.0(5)Rated 5.0 out of 5 from 5 reviews2 hFree cancellationBy Bobby's Bike, Hike & Food Tours - Chicago
Glide through Millennium Park’s ice rink on your Chicago Seasonal Tour, where bright lights and winter fun capture the Chicago Holidays and Christmas spirit.

About this activity

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.
  • ✓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.

Not included

  • ✕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

Meeting and pickup

  • Departure Point: Petterino's (This is the start of your Chicago Seasonal Walking Tour) Directions: You will meet your guide inside of Petterino's restaurant. Please feel free to arrive early to grab a bite or coffee at the restaurant before your tour. Then you'll start your walking tour in Chicago.

Good to know

  • 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.

Cancellation policy

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

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