Unforgettable Small Group Biking Tours from Chicago to Milwaukee

Chicago , United States

Unforgettable Small Group Biking Tours from Chicago to Milwaukee

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About this experience

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

Available options

Unforgettable Small Group Biking Tours from Chicago to Milwaukee

What's included

Bunch at Blue's Egg

Featured Milwaukee City Tour

Hotel Breakfast Sunday morning

Dinner in Milwaukee

1 Night Stay in the Hilton Milwaukee

Air-conditioned vehicle

Bike Pump at the pickup location

Route Planning and safety vehicle

Lunch at Anna's on the Lake on Saturday. Lunch in Milwaukee on Sunday

What you'll see

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.

What's not included

Bikes and biking gear. Riders need to bring all the gear to bike safely.

Available languages

Guide guide

Important information

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

Meeting point

Bikers will be asked to arrive at the meet-up location at 7am on Saturday morning with everything they need for the ride. Before rolling out, your guide will conduct a morning brief to review the route, safety protocols and address any concerns or preferences among the riders.

About Chicago

Chicago is a vibrant city known for its stunning architecture, rich cultural heritage, and world-class cuisine. Situated along the shores of Lake Michigan, it offers a unique blend of urban excitement and natural beauty, making it a must-visit destination for travelers from around the globe.

Top Attractions

Millennium Park

Millennium Park is a famous public park in downtown Chicago, known for its modern art and architecture. It's home to the iconic Cloud Gate sculpture, also known as 'The Bean'.

Park 1-2 hours Free

Art Institute of Chicago

One of the oldest and largest art museums in the United States, the Art Institute of Chicago houses an impressive collection of artworks from around the world.

Museum 2-3 hours $25 (adults), Free for children under 14

Skydeck Chicago

Located on the 103rd floor of the Willis Tower, Skydeck Chicago offers breathtaking views of the city and Lake Michigan. Visitors can step out onto The Ledge, a glass balcony extending out from the building.

Observation Deck 1-2 hours $28 (adults), $20 (children 3-11)

Navy Pier

Navy Pier is a 3,300-foot-long pier on the Chicago shoreline of Lake Michigan. It offers a variety of attractions, including shops, restaurants, and rides.

Entertainment 2-4 hours Free to enter, individual attractions have varying costs

Wrigley Field

Wrigley Field is a historic baseball park located on the North Side of Chicago. It's home to the Chicago Cubs and offers a unique atmosphere for sports fans.

Sports 2-4 hours (game duration varies) Ticket prices vary depending on the game and seating

Must-Try Local Dishes

Deep-Dish Pizza

A thick, buttery crust filled with layers of cheese, toppings, and tomato sauce. It's a Chicago classic and a must-try for pizza lovers.

Dinner Contains gluten and dairy. Vegetarian and vegan options are available at some restaurants.

Chicago-Style Hot Dog

A steamed or grilled all-beef hot dog topped with yellow mustard, chopped white onions, bright green sweet pickle relish, a dill pickle spear, tomato wedges, pickled sport peppers, and a dash of celery salt, all served on a poppy seed bun.

Snack Contains gluten and dairy. Vegetarian and vegan options are available at some hot dog stands.

Italian Beef Sandwich

Thinly sliced beef cooked in its own juices and served on an Italian roll. It's typically dipped in the juices and topped with sweet or hot peppers.

Lunch/Dinner Contains gluten and beef. Vegetarian and vegan options are available at some Italian beef restaurants.

Chicago-Style Popcorn

A sweet and savory snack made with caramel and cheese-flavored popcorn, often sold in colorful boxes at street corners and ballgames.

Snack Contains dairy. Vegetarian and vegan options are available at some popcorn stands.

Popular Activities

Kayaking on the Chicago River Biking along Lake Michigan Rock climbing at First Ascent Picnicking in Millennium Park Yoga in the park Spa treatments at The Peninsula Chicago Visiting the Art Institute of Chicago Attending a performance at the Chicago Symphony Orchestra

Best Time to Visit

May to September

This is the best time to visit Chicago for outdoor activities, festivals, and sightseeing. The weather is warm and pleasant, making it ideal for exploring the city's parks and attractions.

15°C to 30°C 59°F to 86°F

Practical Information

Language

Official: English
Widely spoken: Spanish, Polish, Chinese
English: Widely spoken

Currency

United States Dollar (USD)

Time Zone

Central Time Zone (CT) (GMT-6)

Electricity

120VV, 60HzHz

Safety Information

Overall Safety Rating: Generally safe

Chicago is generally safe for tourists, but visitors should be aware of their surroundings and take precautions to protect themselves and their belongings. Some areas of the city have higher crime rates, and visitors should research their destinations before traveling.

Important Precautions:

• Be aware of your surroundings and keep valuables secure
• Use licensed taxis or ride-sharing services
• Avoid walking alone in isolated or poorly lit areas, especially at night

Getting there

By air

O'Hare International Airport • 27 km (17 miles) from city center
Midway International Airport • 13 km (8 miles) from city center

By train

Union Station, Ogilvie Transportation Center

By bus

Greyhound Station, Megabus Terminal

Getting around

Public transport

The 'L' is a convenient and affordable way to get around Chicago. It consists of eight color-coded lines.

Taxis

Available • Apps: Uber, Lyft

Rentals

Car, Bike, Scooter

Neighborhoods

The Loop Lincoln Park Wicker Park Magnificent Mile Pilsen

Day trips

Navy Pier

2 km (1.2 miles) • Half day to full day

Navy Pier is a 3,300-foot-long pier on the Chicago shoreline of Lake Michigan. It offers a variety of attractions, including shops, restaurants, and rides.

Wrigley Field

10 km (6.2 miles) • Half day to full day

Wrigley Field is a historic baseball park located on the North Side of Chicago. It's home to the Chicago Cubs and offers a unique atmosphere for sports fans.

Museum Campus

3 km (1.9 miles) • Half day to full day

The Museum Campus is a 57-acre park located on the southern tip of Grant Park in Chicago. It's home to several world-class museums, including the Field Museum, the Shedd Aquarium, and the Adler Planetarium.

Festivals

Lollapalooza • Early August (4-day festival) Chicago Jazz Festival • Late August to early September (weekend festival) Chicago Food Festival • Early September (weekend festival)

Pro tips

Visit popular attractions early in the morning or late in the afternoon to avoid crowds and long wait times
Use the Ventra card for easy and convenient payments on public transportation
Explore the city's diverse neighborhoods and culinary scene to get a true sense of Chicago's character and culture
Take an architecture river cruise to see the city's stunning skyline and learn about its architectural history
Visit the city's many parks and outdoor spaces to enjoy nature and outdoor activities, even in the heart of the city