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    1. Local experiences
    2. /Things to do in Chicago…
    3. /Cultural Tours
    4. /City Tours
    5. /Chicago Singles & Solo Travelers Adventure Club
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    Chicago Singles & Solo Travelers Adventure Club

    Explore Chicago through social adventures with fellow solo travelers

    4.9 stars• 2.3K reviews

    Duration

    3-4 hours

    Highlights

    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.

    • Meet new people through shared city adventures
    • Explore Chicago on rotating bike rides, kayaking outings, food tastings, hikes, and social mixers
    • Discover neighborhoods, skyline views, and local culinary experiences
    • Build connections in a low-pressure social setting

    Important details

    • Ages 21+ only
    • Complete the required pre-arrival waiver before you arrive
    • Arrive 15 minutes early for check-in
    • Dress for current weather conditions; outings run rain or shine
    • Stay with your guide for the duration of the event
    • Some dietary restrictions may carry a surcharge and cannot be guaranteed; vegan and gluten-free options are limited

    Cancellation Policy

    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

    FAQs

    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.

    Meeting details

    Bobby's Bike Hike, 540 N. Lake Shore Drive

    Experience provided by Bobby's Bike Hike

    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

    $80.21

    Ages 12+

    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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