Unforgettable Small Group Biking Tours from Chicago to Milwaukee
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Experience an unforgettable small group biking tour from Chicago to Milwaukee, designed to suit various skill levels. We prioritize your safety with every route, taking you to must-see attractions and scenic spots along the way. One highlight is passing by the Bahá’í temple, a unique site listed on the National Register of Historic Places and the only Bahá’í place of worship in North America.
This weekend adventure combines urban excitement with natural beauty. You'll visit landmarks like the Milwaukee Art Museum, the National Bobblehead Hall of Fame Museum, and the Black Holocaust Museum. Milwaukee is also famous for its breweries, including historic names like Schlitz and Pabst, making it a lively destination for beer lovers.
The ride covers mostly flat terrain, shifting between suburban neighborhoods and peaceful bike paths. Expect some headwinds from the lake’s southward winds, so pack accordingly. Our routes are 79% paved and 21% trail, covering approximately 74.6 miles with an elevation change of +963 ft/-1,058 ft. This tour is perfect for adults aged 16-80 with moderate physical fitness.
Join us for a weekend filled with scenic rides, cultural sights, and delicious food. Everything is arranged for your comfort—from hotel stays to meals—so you can focus on enjoying the journey.
Frequently asked questions
What is included in the biking tour?
The tour includes route planning, a safety vehicle, a group gathering at Blue's Egg, Milwaukee city tour, hotel breakfast on Sunday, dinner in Milwaukee, a night at the Hilton Milwaukee, an air-conditioned vehicle, a bike pump at pickup, and lunches at Anna's on the Lake and in Milwaukee.
Do I need to bring my own bike and gear?
Yes, bikes and biking gear are not included. Riders should bring all necessary equipment to ride safely.
How long is the biking route?
The total distance is approximately 74.6 miles, mostly flat terrain, with some headwinds expected along the lake.
What is the group size?
Groups are limited to up to 8 participants, ensuring a personalized experience.
What ages can participate?
This tour is suitable for adults aged 16 to 80 who have at least a moderate level of physical fitness.
Can I cancel my booking?
Yes, you can cancel for a full refund if done at least 24 hours before the scheduled departure. Cancellations within 24 hours are non-refundable and the tour may be canceled due to bad weather or insufficient travelers.
Free cancellation
Full refunds are available if you cancel at least 24 hours before the scheduled departure. Cancellations within 24 hours are non-refundable. The tour may be canceled due to bad weather or low enrollment.
Reserve now
Check a date here, then finish booking with our partner. Payment options are confirmed at checkout.
Duration 34 hours
Check availability to see start times.
Live tour guide
English
Key facts
What's included
Included
- Route planning and safety vehicle
- Group gathering at Blue's Egg
- Featured Milwaukee city tour
- Hotel breakfast Sunday morning
- Dinner in Milwaukee
- 1-night stay at Hilton Milwaukee
- Air-conditioned vehicle
- Bike pump at pickup
- Lunch at Anna's on the Lake on Saturday
- Lunch in Milwaukee on Sunday
Not included
- Bikes and biking gear. Riders need to bring all necessary equipment for safe riding.
Itinerary
Embark on a scenic weekend bike trip from Chicago to Milwaukee, cycling along lakefront trails and exploring iconic landmarks. Highlights include the Bahá’í temple, Milwaukee Art Museum, and a visit to Kenosha for a meal at Anna's on the Lake. The tour offers flexibility for rest stops and plenty of time to enjoy local attractions before returning to Chicago on Sunday afternoon.
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Start and route briefing
Meet at the designated start point at 7am Saturday. Your guide will review the route, safety protocols, and answer any questions before departure.
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Lakefront ride and sightseeing
Cycle along scenic lakefront trails, passing parks, beaches, and notable landmarks like the Home Alone house and Bahá’í temple.
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Lunch in Kenosha
Stop at Anna's on the Lake for a relaxing meal before continuing your ride into Milwaukee.
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Milwaukee city tour and free time
Explore Milwaukee’s top attractions, including City Hall, the Historic Third Ward, and enjoy local cuisine at Blue's Egg. You can also visit breweries and museums at your own pace.
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Overnight at Hilton Milwaukee
Relax, shower, and prepare for the next day's adventures.
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Morning city tour and departure
After breakfast, your guide will take you on a tour of Milwaukee’s highlights before heading back to Chicago around 4-5pm.
Meeting point & pickup
Meet at the starting point
Participants should arrive by 7am on Saturday with all biking gear. A guide will conduct a brief to review the route, safety measures, and address any questions or preferences before starting the ride.
Open in Google MapsCancellation & confirmation
Free cancellation
Full refunds are available if you cancel at least 24 hours before the scheduled departure. Cancellations within 24 hours are non-refundable. The tour may be canceled due to bad weather or low enrollment.
- 100% refund if canceled at least 1 day before
- No refund if canceled within 0–1 days
- May be canceled for bad weather
- May be canceled if not enough travelers
Instant confirmation
Your booking is confirmed immediately after checkout.
From $349.00 per person
- Free cancellation
- Secure checkout with our booking partner
