See holiday lights, market traditions, and Chicago's tree on a downtown stroll
2 hrs
Guided holiday walking tour
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.
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
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.
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.
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 🌟🌟🌟🌟
Lilllian Belford
September 1, 2026
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 🌟🌟🌟🌟
Lilllian Belford
September 1, 2026
Walk Chicago’s must-see sights, including Millennium Park, in 2 hours
Bike Miami Beach and sample local food with a guide
Taste Chicago classics and discover the stories behind the city’s signature dishes
Paddle Lake Michigan from Ohio Street Beach for two hours
Rent a bike by Chicago’s Lakefront Trail with maps, helmet, lock, and easy access near Navy Pier
Rent a bike for 24 hours near the Lakefront Trail and Navy Pier