Unforgettable Small Group Biking Tours from Chicago to Milwaukee
Overview
Our tours have varying difficulty levels to accommodate different skill levels. We take every safety precaution available to prioritize your well-being. Our routes that take you to must-see attractions and beautiful destinations. The Bahāʾī temple that we will pass is listed on the National Register of Historic Places and the only Bahāʾī place of worship in North America.
This weekend vacation to Milwaukee is a vibrant mix of urban excitement and nature. Notable spots that riders can visit are the Milwaukee Art Museum, the National Bobblehead Hall of Fame Museum, and the Black Holocaust Museum. The city is also home to over 40 breweries, with iconic names like Schlitz and Pabst leading the way.
On the ride you'll traverse mostly flat terrain that shifts between suburban areas and secluded bike paths. Expect southward winds along the lake, be prepared to experience some headwinds during your ride.
Roads: 79% paved, 21% trails
Distance: 74.6 miles
Elevation: +963 ft/ - 1,058 ft
What's Included
- Breakfast Hotel Breakfast Sunday morning
- Brunch Bunch at Blue's Egg
- Dinner Dinner in Milwaukee
- Lunch Lunch at Anna's on the Lake on Saturday. Lunch in Milwaukee on Sunday
- Featured Milwaukee City Tour
- 1 Night Stay in the Hilton Milwaukee
- Air-conditioned vehicle
- Bike Pump at the pickup location
- Route Planning and safety vehicle
- Bikes and biking gear. Riders need to bring all the gear to bike safely.
Meeting Location
West Wolfram Street
Chicago, IL 60657, USA
Detailed check-in instructions, including the exact address, are provided with your booking confirmation.
This activity ends back at the meeting point.
What To Expect
Embark on an unforgettable weekend bike getaway to Milwaukee. Cycle along the scenic lakefront trail, where you'll discover stunning parks and some of the best riding paths in the area. Your group will stop to see landmarks such as the iconic Home Alone house and the stunning Bahāʾī temple. Your group will roll into Kenosha where you will go to one of the area's best restaurants, Anna's on the Lake. Of course riders have full say of how often rest stops are made to ensure everyone has a comfortable and safe ride. Arrive to the Hilton Milwaukee where you will have time to shower and change before dinner.
Start the next day with breakfast at the hotel. After, you will meet your tour guide who will take you on a tour of Milwaukee’s best attractions and reveal to you all the city’s biggest secrets. You will visit the City Hall, and Historic Third Ward before enjoying some of the city’s best food at Blue’s Egg. After lunch, you will have free time to explore some of Milwaukee's unique attractions, including its renowned breweries and captivating museums. Return to Chicago by car between 4-5pm on Sunday, where you'll be able to collect your bike and bags from the drop off location.
Additional Info
- Confirmation is instant and will be received at time of booking
- Not recommended for travelers with spinal injuries
- Not recommended for pregnant travelers
- Not recommended for travelers with poor cardiovascular health
- Travelers should have at least a moderate level of physical fitness
- This tour/activity will have a maximum of 8 travelers
Frequently Asked Questions
(10)Q: Are there any weight restrictions for kayaking?
Cancellation Policy
Still have questions?
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Activity code: C-5525582P1
Additional Info
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Frequently Asked Questions (10)
The answers provided below were previously given in response to questions from City Boat Tours customers.
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The maximum weight capacity for kayaking is 340 lbs / 154 kg.
Nov 2021No experience is necessary! Beginners are welcome on all of our kayak tours. Most of our guests have never been in a sea kayak before. Anyone in average physical condition may join a kayak tour. If you can hike or bike, you can paddle our sea kayaks. You do not need any swimming skills either.
The only prerequisite is a healthy spirit of curiosity and adventure.
Regardless of age or skill level you will find that our expeditions offer enough flexibility to make your experience with us safe and rewarding. We will show you proper sea kayaking technique and water safety before leaving the beach. And your expert guides will be with you throughout the adventure to give you pointers and improve your skills.
Sep 2022Your safety is City Boat Tours‘s number one concern. In general, sea kayaking is safer than most other outdoor pursuits, even bicycling.
Jan 2023- For a full refund, you must cancel at least 24 hours before the tour start time.
- If you cancel less than 24 hours before the tour start time, the amount you paid will not be refunded.
- Any changes made less than 24 hours before the tour start time will not be accepted.
- Cut-off times are based on the tour local time (CDT).
- This tour 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.
- Breakfast. Hotel Breakfast Sunday morning.
- Brunch. Bunch at Blue's Egg.
- Dinner. Dinner in Milwaukee.
- Lunch. Lunch at Anna's on the Lake on Saturday. Lunch in Milwaukee on Sunday.
- Featured Milwaukee City Tour.
- 1 Night Stay in the Hilton Milwaukee.
- Air-conditioned vehicle.
- Bike Pump at the pickup location.
- Route Planning and safety vehicle.
- Bikes and biking gear. Riders need to bring all the gear to bike safely.
This tour requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.
Apr 2025The minimum age to participate is 16..
Apr 2025If a date or time is not listed on the calendar, it’s sold out or unavailable for another reason. Support cannot assist further if a date or time is not on the calendar.
If you find a date and time that works for you, book it NOW because things always sell out at this time of year.
Apr 2025Accessibility information for the Unforgettable Small Group Biking Tours from Chicago to Milwaukee is as follows:
- Not recommended for travelers with spinal injuries
- Not recommended for pregnant travelers
- Not recommended for travelers with poor cardiovascular health
- Travelers should have at least a moderate level of physical fitness
Detailed check-in instructions – including meeting point address, Google map, and parking information – for Unforgettable Small Group Biking Tours from Chicago to Milwaukee will be included in your confirmation email from City Boat Tours. Please be sure to double and triple check your email address is correct at checkout so this important email makes its way to you!
Mar 2024What's Included
- BreakfastHotel Breakfast Sunday morning
- BrunchBunch at Blue's Egg
- DinnerDinner in Milwaukee
- LunchLunch at Anna's on the Lake on Saturday. Lunch in Milwaukee on Sunday
- Featured Milwaukee City Tour
- 1 Night Stay in the Hilton Milwaukee
- Air-conditioned vehicle
- Bike Pump at the pickup location
- Route Planning and safety vehicle
- Bikes and biking gear. Riders need to bring all the gear to bike safely.
Additional Info
- Confirmation is instant and will be received at time of booking
- Not recommended for travelers with spinal injuries
- Not recommended for pregnant travelers
- Not recommended for travelers with poor cardiovascular health
- Travelers should have at least a moderate level of physical fitness
- This tour/activity will have a maximum of 8 travelers
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