Explore Chicago through social adventures with fellow solo travelers
3-4 hours
Join a monthly club designed for singles and solo travelers to explore Chicago together. Connect through guided outings that spotlight the city’s neighborhoods, skyline, and food scene.
Cancel at least 72 hours before the tour for a full refund minus a 10% credit card processing fee. No cancellations within 72 hours. Weekend changes within 72 hours incur a $10 per-person service fee. A minimum of 2 people is required; if not met 2 hours before, the tour may be canceled with a full refund. Full refund if the operator cancels due to severe weather.
Product ID: 59MVC8
Join only if you are 21 or older.
Bring a bottle of water and a camera.
Dress for current weather conditions and wear comfortable walking shoes and clothes. Bring rain gear (umbrella or poncho) if rain is expected, and consider layers because conditions can shift near the lake.
Bobby's Bike Hike, 540 N. Lake Shore Drive
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
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