TourTruth score 9.2 out of 10
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Chicago Biking Tour to Milwaukee 34 hr
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Rated on 1 provider · Why
- Chicago
- Updated October 31, 2026
Ride 74.6 miles from Chicago to Milwaukee on a supported weekend trip with meals, a hotel stay, and a guided city tour.
About this tour
Trade Chicago’s city streets for a long-distance ride to Milwaukee, with lake views, quiet paths, and a weekend of urban discoveries along the way. This Chicago biking tour to Milwaukee covers 74.6 miles over mostly flat terrain, with a mix of suburban roads and secluded bike paths. The route includes 963 feet of climbing and 1,058 feet of descent, and southward winds along the lake can bring headwinds.
Meet at 7:00 a.m. Saturday for a guide-led briefing on the route and safety before setting off. The weekend includes lunch at Anna’s on the Lake, dinner in Milwaukee, a night at the Hilton Milwaukee, Sunday breakfast, and a featured city tour. Along the way, pass the Bahá’í temple, the only Bahá’í place of worship in North America and a National Register of Historic Places landmark. Milwaukee offers museums, lakefront sights, and a brewing history tied to names such as Schlitz and Pabst.
Bring your own bike and safety gear; a pump is available at the pickup location. Choose this Chicago biking tour to Milwaukee for a supported ride that pairs open-road effort with a full weekend of city highlights.
Highlights
- Ride south from Chicago to Milwaukee across mostly flat terrain
- Follow a route that blends suburban roads with secluded bike paths
- Pass the Bahá’í temple, a National Register of Historic Places landmark
- Explore Milwaukee’s museums, lakefront sights, and brewery heritage
What's included
Included
- Route planning and safety vehicle
- Breakfast at Bunch at Blue's Egg
- Featured Milwaukee city tour
- Sunday hotel breakfast
- Dinner in Milwaukee
- One-night stay at the Hilton Milwaukee
- Air-conditioned vehicle
- Bike pump at the pickup location
- Saturday lunch at Anna's on the Lake
- Sunday lunch in Milwaukee
Not included
- Bikes and biking gear; riders must bring all equipment needed to bike safely
Ratings on each provider
The ratings and review counts each booking site shows for this tour.
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Important information
- Meet at 7:00 a.m. Saturday with everything needed for the ride
- The guide gives a morning briefing on the route and safety protocols before departure
- A moderate level of physical fitness is recommended
- Not recommended for travelers with spinal injuries, pregnant travelers, or travelers with poor cardiovascular health
- The route is 74.6 miles, with 79% paved roads and 21% trails
- Expect possible headwinds along the lake
How this score is calculated
This tour has no TourTruth score yet: Viator doesn't show a usable rating for it. It gets a score as soon as a provider lists one.
How the score works
- Each provider rating is turned into a percentile: the share of that provider's ratings it beats, weighted by review counts.
- Listings on different providers are combined in proportion to their review counts.
- Tours with few reviews are pulled toward the average until more reviews come in, so a handful of perfect reviews can't top the list.
- The result is shown from 0 to 10. Tours without a usable provider rating are not scored.
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