Milwaukee 1-Day Tour from Chicago
Milwaukee 1-Day Tour from Chicago
Discover the legacy of Harley-Davidson, explore the bustling Milwaukee Public Market, tour a renowned brewery, and admire the stunning architecture of the Milwaukee Art Museum before returning to Chicago.
Itinerary:
Chicago → Milwaukee → Harley-Davidson Museum (Optional, 90 mins) → Milwaukee Public Market (90 mins) → Miller Brewery Tour and Samples Tasting (Optional, 90 mins) → Lakefront & Milwaukee Art Museum (Outside Visit, 30 mins) → Chicago
Harley-Davidson Museum (Optional, 90 mins): Explore over 100 years of motorcycle history with 450+ rare bikes and artifacts.
Milwaukee Public Market (90 mins): Stroll through a vibrant indoor market with specialty food vendors, fresh produce, and artisan crafts.
Miller Brewery Tour (Optional, 90 mins): Learn about 155 years of brewing tradition, tour the facility, and enjoy beer samples (21+).
Lakefront & Milwaukee Art Museum (Outside Visit, 30 mins): Admire the architectural beauty of this renowned museum and enjoy scenic lake views.
Milwaukee Fall Foliage Tour (10/04/2025-11/02/2025)
For a breathtaking autumn experience, choose our special maple-viewing route. Witness vibrant red, orange, and yellow hues across Wisconsin’s stunning landscapes while visiting serene parks, historic sites, and picturesque lakefronts.
Itinerary:
Chicago → Milwaukee → Back Bay Park (60 mins) → Holy Hill Basilica (60 mins) → Lake Geneva (90 mins, optional cruise) → Chicago
Back Bay Park (60 mins): A charming park with towering oak trees, playgrounds, and scenic lake views—perfect for a relaxing break.
Holy Hill Basilica (60 mins): Perched atop the highest point in Southeastern Wisconsin, this historic church offers panoramic views of colorful maple forests. Climb the bell tower for a stunning overlook of the fall foliage.
Lake Geneva (90 mins): Stroll the scenic Shore Path for breathtaking views of historic estates, sailboats, and golden autumn reflections on the lake. Opt for a cruise to experience the beauty from the water.
Enjoy the magic of Milwaukee and its fall landscapes before heading back to Chicago!
About this activity
Free cancellation
Cancel up to 24 hours in advance for a full refund
Reserve now & pay later
Keep your travel plans flexible — book your spot and pay nothing today.
Duration 1 day
Check availability to see starting times
Live tour guide
English
Highlights
- Immerse yourself in the world of motorcycles at the Harley-Davidson Museum
- Learn about the history of brewing and enjoy samples of beer at Miller Brewery
- Visit the Milwaukee Art Museum,one of the largest art museums in the US
- Explore the Milwaukee Public Market, home to 24 unique specialty food vendors
- Return to Boston with unforgettable memories.
Description
Inclusions
- Professional driver and guide (or driver-guide)
- Professional vehicles transportation (Vehicle used based on the number of guests attending that day)
- Taxes
Traveler Ratings
See how travelers have rated this attraction. Check out the average rating and read what others have shared about their experiences
5.0 / 5
5 out of 5 stars
Based on 3 reviews
Review histogram
5
- 0%
4
- 0%
3
- 0%
2
- 0%
1
- 0%
Traveler Reviews
Discover what other travelers have to say about this attraction. Read their reviews and get insights into their experiences
Related Attractions
Explore similar attractions that other travelers have enjoyed. Discover more options to enhance your travel experience
Milwaukee River Kayak RentalMilwaukee River Kayak Rental
The Milwaukee River has many breweries and restaurants along its shores, but driving can be a bit of a hassle. Bypass the roads and take to the water with this Milwaukee River Kayak Rental. Float down the river at your own pace without being ...
$55
per adult
Private Downtown Milwaukee Helicopter RidePrivate Downtown Milwaukee Helicopter Ride
The Milwaukee Downtown ride takes you on a on an exhilarating helicopter journey down the Milwaukee Bay where you can witness Downtown Milwaukee like never before! This ride offers a truly unique perspective, soaring directly over the heart o...
$149
per adult
MilwaukeeTandem Kayak RentalMilwaukeeTandem Kayak Rental
Rent a tandem kayak from a shop on the banks of the Milwaukee River and spend four hours exploring the tranquil waters at your own pace. The shop’s convenient location means you can get right on the water without strapping kayaks to your car ...
$90
per adult
Milwaukee: Small-Group Sights and History TourMilwaukee: Small-Group Sights and History Tour
Swap the big bus tours for a crowd-free experience. Traveling in an open-air, five-seater electric vehicle, you'll thoroughly explore the historic city of Milwaukee, from popular tourist destinations to some hidden gems that most visitors mis...
$67
per adult
The Grand Walk: A Self-Guided Audio Tour through MilwaukeeThe Grand Walk: A Self-Guided Audio Tour through Milwaukee
________ PLEASE NOTE: This is a self-guided audio tour, not an entry ticket to the Milwaukee Art Museum. The tour ends in front of the museum. If you wish to visit the museum after the tour, you can purchase entry tickets separately. ________...
$7
per adult
2-Hour Bus Tour in Milwaukee City2-Hour Bus Tour in Milwaukee City
This experience is for the budget friendly travelers. This bus tour has a minimum 8 guest requirement to operate. A 90-120 minute Tour Times: 10am. Embark with fellow guests on an unforgettable journey through the heart of Milwaukee, w...
$40
per adult
Interior Architecture Walking Tour Inside the LoopInterior Architecture Walking Tour Inside the Loop
Discover the hidden gems of Chicago’s Loop area on a walking tour that showcases the best of the neighborhood’s stunning interiors and architectural must-sees. Step behind the facades to explore beautifully designed interiors—from art deco sp...
$35
per adult
2-Hour Chicago Lakefront & Museum Campus Segway Tour2-Hour Chicago Lakefront & Museum Campus Segway Tour
Explore Chicago by Segway with the benefit of a scenic 7- or 8-mile tour led by your guide. Start with an orientation to operating the Segway and a few minutes to practice. Then roll through the paths of Grant Park to Buckingham Fountain and ...
$64
per adult
Lakefront, Museum Campus Small-Group Segway TourLakefront, Museum Campus Small-Group Segway Tour
Experience Chicago in a new way on this small-group Segway tour. Visit Chicago’s ‘front yard,’ the beautiful lakefront and 57-acre Museum Campus. Glide along the fragrant floral paths of Grant Park to the famous Buckingham Fountain. Then, tra...
$64
per adult
Art Institute of Chicago Guided Tour and Skip the Line TicketArt Institute of Chicago Guided Tour and Skip the Line Ticket
Make the most of your time at the Art Institute of Chicago by avoiding the crowds to get in. Whether you’re an art aficionado or beginner, this opportunity lets your learn about the museum and its pieces through the eyes of an art historian g...
$74
per adult
Chicago Murder Mystery and Sightseeing Walking TourChicago Murder Mystery and Sightseeing Walking Tour
Bored of traditional walking tours? Try an experience that mixes sightseeing with an engaging game in this murder mystery tour through Chicago. Play as a detective and a suspect as you wander through various neighborhoods and see the city. Le...
$35
per adult
Art Institute of Chicago Small-Group Highlights TourArt Institute of Chicago Small-Group Highlights Tour
Explore one of the country’s great art museums—and discover many of its collection highlights—on this small-group Art Institute of Chicago tour. Meet your guide right out front, and see works from artists the likes of Picasso, Chagall, Seurat...
$90
per adult
Downtown Chicago Architecture, Art, and History Walking TourDowntown Chicago Architecture, Art, and History Walking Tour
This walking tour is a feast for the eyes, combining art, architecture, and history as you navigate through bustling downtown Chicago. In a small group, you’ll marvel at skyscrapers and mosaic murals as you discover stories and secrets about ...
$33
per adult
West Side Neighborhoods Foodie Small-Group Bike TourWest Side Neighborhoods Foodie Small-Group Bike Tour
Make your way to Chicago's Streeterville neighborhood near Navy Pier to meet your guide and group. Get set up with your helmet and bike, then pedal off through the River North neighborhood, across the Chicago River, and over to Fulton ...
$99
per adult
Chicago Small-Group Digital and Polaroid Photo ShootChicago Small-Group Digital and Polaroid Photo Shoot
Don’t leave Chicago without taking home professional digital and polaroid shots of your visit. Starting from the iconic Millennium Park, your photographer guide takes you to some of the city’s most photogenic landmarks to take photos of you t...
$169
per adult
Private Lake Michigan Sailing Charter and Sightseeing Chicago Skyline CruisePrivate Lake Michigan Sailing Charter and Sightseeing Chicago Skyline Cruise
Enjoy a private two and a half hour sailing experience for up to four people along Chicago’s beautiful lakefront. Kick back, relax, and let the US Coast Guard licensed captain treat you to stunning views of Chicago’s spectacular skyline. Make...
$488
per adult
Chicago Lake Michigan Private Sunset Sailing CharterChicago Lake Michigan Private Sunset Sailing Charter
Soak up unbeatable views of Lake Michigan and the Chicago skyline—and stay on the water long enough to watch the lights come on in the city—on this private, sunset sailing tour. This charter is completely customizable, giving you the chance t...
$508
per adult
Historical and Architectural Chicago Fireboat River/Lake CruiseHistorical and Architectural Chicago Fireboat River/Lake Cruise
Travel on a piece of history, learning Chicago fire history as well as Architecture! We travel on Lake Michigan and through the Chicago River seeing the sights. Perfect for Fire enthusiasts, families and everyone in between! Our flagship vess...
$45
per adult
Lincoln Park Hauntings Ghost Investigation TourLincoln Park Hauntings Ghost Investigation Tour
Arrive at Lincoln Park after dark, leaving room in your day to complete other activities on your itinerary. Join forces with your personal paranormal investigator and begin to take a leisurely stroll through the neighborhood.Delve into...
$40
per adult
Chicago River Architecture Cruise History and Sightseeing TourChicago River Architecture Cruise History and Sightseeing Tour
Make your way to either Navy Pier or Michigan Avenue (depending on option chosen) for your cruise departure. Board your riverboat and find a comfortable seat; a restroom is available on the boat. Listen as your guide, an architecture e...
$49
per adult
45-Minute Private Helicopter Flight for 1-3 People45-Minute Private Helicopter Flight for 1-3 People
Enjoy spectacular views of Chicago from an MD500 helicopter. This helicopter flight over Chicago covers all the important highlights of the city from McCormick Place and Soldiers Field in the South to Wrigley Field in the North. Depart from Schaumbu...
$756
per adult
Architecture cruise in Spanish on the Chicago River from Michigan AveArchitecture cruise in Spanish on the Chicago River from Michigan Ave
This picturesque cruise is led by a professional Spanish speaking guide who shares exciting details and the historical significance of the buildings that line the Chicago River. Boarding at the dock on Michigan Avenue, you'll sail down all th...
$54
per adult
Chicago American Writers Museum Skip-the-Line Admission TicketChicago American Writers Museum Skip-the-Line Admission Ticket
Immerse yourself in American literary traditions, and enjoy a wide range of interactive exhibitions, during a visit to Chicago’s one-of-a-kind American Writers Museum. Conveniently located on Michigan Avenue, the museum was established in 201...
$16
per adult
The Art Institute of Chicago: Fast PassThe Art Institute of Chicago: Fast Pass
Home to some of the world's most recognizable artworks, the Art Institute of Chicago is America's second-largest art museum. Seeing famous art at the Art Institute of Chicago is a reliable way to ensure your day in the Windy City is nothing short of ...
$40
per adult
The Art Institute of Chicago: Fast PassThe Art Institute of Chicago: Fast Pass
Home to some of the world's most recognizable artworks, the Art Institute of Chicago is America's second-largest art museum. Seeing famous art at the Art Institute of Chicago is a reliable way to ensure your day in the Windy City is nothing s...
$40
per adult
Chicago History Museum: Entry TicketChicago History Museum: Entry Ticket
Explore the history of Chicago and United States through permanent and temporary exhibitions drawn from more than 20 million items in the Chicago History Museum. Showcasing photography, documents, artifacts, and interviews, the permanent and ...
$17
per adult
Chicago CityPASS®: Save up to 49% at 5 Top AttractionsChicago CityPASS®: Save up to 49% at 5 Top Attractions
Experience 5 must-see attractions and save up to 49% with Chicago CityPASS® tickets. One simple purchase removes the stress of planning, so you can relax and enjoy your memories in the making. With 9 days to use your tickets, you’ll have plenty of ti...
$126
per adult
American Writers Museum Flexible Date Entry TicketAmerican Writers Museum Flexible Date Entry Ticket
Learn about the history of writing and how it has shaped American culture with a ticket to the American Writers Museum in Chicago. Stroll through exhibits that appeal to all 5 senses, explore the intricacies of language through games, and write your ...
Go City | Chicago All-Inclusive PassGo City | Chicago All-Inclusive Pass
Welcome to the windy city! Home to world-famous art museums, iconic architecture and delicious food, Chicago is a perfect blend of midwestern hospitality and dynamic urban metropolis all set against the beautiful backdrop of Lake Michigan. Do...
$139
per adult
Color Factory Chicago General Admission TicketColor Factory Chicago General Admission Ticket
Voted the #1 Immersive Art Experience in America by USA Today readers in 2024, Color Factory Chicago celebrates the joy of color. Embark on a bright and colorful journey through 14+ immersive installations that inspire joy and human connection, expa...
$32
per adult
360 Chicago Observation Deck: Skip The Line Entry Ticket360 Chicago Observation Deck: Skip The Line Entry Ticket
It might be called the Windy City but from the 94th floor of downtown Chicago's John Hancock Center, you'll see a lot more than windswept trees. 360 Chicago offers incredible views of the city and Lake Michigan, plus four neighboring states. ...
$30
per adult
Willis Tower Skydeck and The Ledge TicketWillis Tower Skydeck and The Ledge Ticket
Enjoy an unrivaled view over the city of Chicago on a trip up the city's Willis Tower. This famous building, once known as the Sears Tower, is not only home to a Skydeck on the 103rd floor, but it also features The Ledge, a series of 4 glass-paneled ...
$29
per adult
Navy Pier Centennial Wheel TicketNavy Pier Centennial Wheel Ticket
Experience the views from the Centennial Wheel at the Historic Navy Pier in Chicago with this attraction ticket. Be suspended over Lake Michigan at the mouth of the Chicago River. Marvel at the Chicago skyline and gaze out over the sparkling waters o...
$20
per adult
360 Chicago Observation Deck Fast Pass Ticket360 Chicago Observation Deck Fast Pass Ticket
Travel to the 94th floor of the former John Hancock Center in just 40 seconds on one of North America’s fastest elevators. Step foot onto the observation deck to experience breathtaking views of the Chicago Skyline and Lake Michigan. Take in the cit...
$49
per adult
360 Chicago Observation Deck Sip and View Ticket360 Chicago Observation Deck Sip and View Ticket
Take in the beautiful views of Chicago as you enjoy a drink from our carefully curated Sip menu. 360 CHICAGO Observation Deck sits 1,000 feet over Chicago’s legendary Michigan Avenue. Located on the 94th floor of 875 N. Michigan (formerly the John Ha...
$39
per adult
Chicago Skyline PassChicago Skyline Pass
From stuffed pizza crusts to windswept walks, Chicago is one American city that wants to entertain you! This specially curated package has been designed to tick-off sky-high views and the city's best architecture from your to-do list. Get easy ac...
$120
per adult
360 Chicago Observation Deck General Admission360 Chicago Observation Deck General Admission
360 CHICAGO Observation Deck sits 1,000 feet over Chicago’s legendary Michigan Avenue. Located on the 94th floor of 875 N. Michigan (formerly the John Hancock Center), 360 CHICAGO gives you the opportunity to experience the best views of the Chicago ...
$27
per adult
360 Chicago Observation Deck Tickets360 Chicago Observation Deck Tickets
360 CHICAGO’s concourse level includes an interactive exhibit highlighting the history of Chicago and the vibrant cultures and businesses across Chicago neighbourhoods. Get inspired to explore Chicago beyond downtown after watching a short do...
$30
per adult