Explore our promoted experiences
- Food and walking holiday tour of downtown Chicago
- Visit the German-style Christkindlmarket, a festive outdoor market with warming cider and holiday shops
- Stop at a local bar to taste seasonal craft brews
- Head to the historic Palmer House Hotel, where brownies were invented, to try the popular chocolate treat
- Admire the outdoor ice skating rink and magnificent architecture at Millennium Park
- Sample Chicago's famous deep dish pizza at a festive restaurant
- See Chicago's most majestic Christmas tree display at Millennium Park
- Taste the famous Chicago-style hot dog
Departure & Return
Departure Point: Lou Malnati's Pizzeria - Wrigley Building Directions: Please note that the entrance is located on the Northside of the Wrigley Building - ground level. Your guide will be wearing a Bobby's Bike Hike shirt and paddle.
What To Expect
Head to Millennium Park, the location of a large outdoor ice rink sitting smack among the famous landmark buildings of downtown Chicago. See the city's official Christmas tree, lit up for the season, and watch hundreds of skaters enjoy the free recreational activity.
As you walk, stop for a brownie sample at the Palmer House Hotel, where the classic dessert was invented. See the magnificent interior architecture of this famous hotel, where many notable people have slept since its founding in 1875. Stop by a local bar to warm up and sip a unique Chicago craft beer. Stop by a local institution to try some of Chicago's famous deep-dish pizza.
Visit the traditional German-American Christkindlmarket, a large open-air Christmas festival. Taste authentic hot apple cider and browse the handicrafts and traditional European products for the perfect gift or souvenir. You may come across model trains, a Santa house or a Christmas choir during your exploration.
Follow your guide to State Street where the lights, decorations, and window displays dazzle. You'll also stop at a local shop to try the famous Chicago-style hot dog.
After your tour concludes, and you are free to explore Chicago's festive streets on your own.
- Confirmation will be received at time of booking
- Operates in all weather conditions, please dress appropriately
- Wheelchair accessible
- Near public transportation
- All of our walking tours at the present moment do allow for ADA compliant and wheelchair accessible. But please note that sometimes our restaurants change and we cannot guarantee every restaurant will not include stairs of some sort which might make things difficult. But a majority of our stops should be ADA compliant.
- Travelers should have a moderate physical fitness level
- This tour/activity will have a maximum of 15 travelers
- OPERATED BY Bobby's Bike Hike - Chicago
- For a full refund, you must cancel at least 24 hours before the experience’s start time.
- If you cancel less than 24 hours before the experience’s start time, the amount you paid will not be refunded.
- Any changes made less than 24 hours before the experience’s start time will not be accepted.
- Cut-off times are based on the experience’s local time.
- This experience 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.
Learn more about cancellations.
- Face masks required for travelers in public areas
- Face masks required for guides in public areas
- Hand sanitizer available to travelers and staff
- Social distancing enforced throughout experience