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    1. Local experiences
    2. /Things to do in Chicago…
    3. /Specialty Tours
    4. /Seasonal and Holiday
    5. /Chicago Holiday Walking Tour
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    Chicago Holiday Walking Tour

    See holiday lights, market traditions, and Chicago's tree on a downtown stroll

    4.9 stars• 2.3K reviews

    Duration

    2 hrs

    Includes

    Guided holiday walking tour

    Highlights

    Explore downtown Chicago on a guide-led walking tour built around winter holiday displays and seasonal traditions. This walking-only experience runs from late November through Christmas Eve.

    • See the lights of the Magnificent Mile
    • Experience German-inspired festivities at Christkindlmarket
    • Walk up to Chicago's holiday tree

    Important details

    • All ages welcome
    • Complete the pre-arrival waiver before you arrive
    • Arrive 15 minutes early for check-in; late arrivals may be rebooked
    • Tours run in rain, snow, or shine
    • Stay with your guide throughout the tour

    Cancellation Policy

    Cancel at least 72 hours before start for a refund minus a 10% processing fee. No refunds or rescheduling within 72 hours. Changes outside 72 hours may have a rescheduling fee. Tours run in rain or snow. If the operator cancels due to weather or unforeseen circumstances, you’ll receive a full refund. A minimum of 4 participants is required; if it is not met 2 hours before start, the tour may be rescheduled or canceled with a full refund.

    Product ID: HGT7UB

    FAQs

    No. This is a walking-only tour, and food is not included.

    Bring a bottle of water and wear comfortable walking shoes and clothing. Dress for current conditions, with rain gear if rain is expected and warm layers in cold or snowy weather.

    Yes. The holiday walking tour may end up to 15 minutes before or after its scheduled end time.

    Experience provided by Bobby's Bike Hike

    Related locations

    How can we help?

    We are here to assist with special requests, large groups, last minute needs, and any questions you may have.

    Call or text 1-877-GREET-WELL

    Report an issue

    Adult

    $34.86

    Ages 12+

    0

    Youth - (Fri-Sun)

    $30.21

    Ages 4-11

    0

    Infant - (Fri-Sun)

    $11.61

    Ages 0-3 (when sharing w/ Adult)

    0

    Why book through Greetwell?

    • No Added Fees

      No booking or service fees, ever

    • Concierge Support Included

      Real humans ready to help with timing, questions, or special requests

    • Free Cancellation Available

      Most experiences can be cancelled for a full refund

    Discover what we've curated for you

    Review summary

    4.9
    Excellent
    2.3K reviews•Google Maps
    1,911
    36
    14
    4
    11

    The guides here are consistently stellar, and travelers are quick to name them. Joe, Jeff, Jessika, and several others get enthusiastic shout-outs for being knowledgeable, funny, and genuinely caring hosts who make everyone feel comfortable. These aren't just rehearsed tours – guides share insider tips on where to eat later, adjust for weather needs, and greet past guests like old friends when they bump into them around the city. The food and bike tours seem to be the crowd favorites, taking groups through Chicago's iconic dishes at signature spots while weaving in local history and hidden gems. The routes avoid busy streets when possible, bikes are well-maintained and comfortable, and groups stay small enough that everyone feels looked after. Whether you're exploring downtown, Chinatown, or neighborhood breweries, expect a good mix of sightseeing, storytelling, and excellent eating. Several people mention doing the tour early in their visit so they can revisit favorite spots discovered along the way.

    What people are saying

    Review 1 of 5
    5/5

    Went on a tour of Chinatown with York and I had a great time. He was so kind and very knowledgeable, and the food we ate was amazing 🌟🌟🌟🌟

    Photo of Lilllian Belford

    Lilllian Belford

    September 1, 2026

    Review 1 of 1
    5/5

    Went on a tour of Chinatown with York and I had a great time. He was so kind and very knowledgeable, and the food we ate was amazing 🌟🌟🌟🌟

    Photo of Lilllian Belford

    Lilllian Belford

    September 1, 2026

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