Chicago to Milwaukee Day Trip: Harley-Davidson Museum & Art

Milwaukee's industrial heritage and art scene fit inside a single day from Chicago.

A day trip from Chicago to Milwaukee with professional guide and round-trip transportation, visiting the Harley-Davidson Museum, Milwaukee Public Market, Miller Brewery and Milwaukee Art Museum. The itinerary covers the city's brewing legacy and cultural landmarks, with optional brewery admission and tastings. During autumn, a seasonal foliage upgrade routes the tour through Back Bay Park, Holy Hill Basilica and Lake Geneva instead.

The experience

The tour departs Chicago in the morning and heads north to Milwaukee, where a professional driver and guide handle the route while you settle in for the drive. Your first stop is the Harley-Davidson Museum, where 90 minutes lets you walk through the brand's history from its origins to modern machines. After the museum, the Milwaukee Public Market in the historic Third Ward gives you time to browse Wisconsin specialties (cheese, sausage, local goods), and grab lunch if you want it.

Miller Brewery comes next, with an optional 90-minute tour and beer samples available at your own cost. The brewery's schedule may shift the itinerary if it's closed on your departure date. The Milwaukee Art Museum rounds out the cultural stops with an outside visit to see the building's iconic wings. You return to Chicago in the evening, having covered the city's industrial backbone and its art collection without managing the drive yourself.

From January 1, 2027, the itinerary shifts slightly to lead with the Milwaukee Art Museum before the Harley-Davidson Museum, and the Pabst Mansion (the "Beer King's" estate) substitutes for Miller Brewery if the brewery is closed that day. During autumn foliage season, you can upgrade to a different route entirely: Back Bay Park for 60 minutes of maple viewing and hiking along Lake Michigan, then Holy Hill Basilica overlooking colorful forests, and finally Lake Geneva where an optional lake cruise (at your own expense) lets you see the autumn landscape from the water. Both versions return you to Chicago by evening.

What’s included

• Professional vehicle transportation matched to your group size.
• professional driver and guide throughout the day.
• round-trip transportation from Chicago to Milwaukee and back.

Information

Lasts 1d, runs Friday and Saturday at 08:00, from US$ 125 per person, with a live guide in English and with free cancellation up to 24 h before.

Days and timesFriday and SaturdayDeparts at 08:00Last departure this season: 11 DecAnother day? ›

GroupUp to 55

Live guideEnglish

Meeting point and pickupNo hotel pickup: you go to the meeting point. Ends back at the starting point.

Book up to4h before

AgesAdult (13 and older) · Child (3 to 12 years) · Infant (under 3)

Cancellation and refundsFree cancellation up to 24 h before the start. After that, no refund.It may be canceled due to bad weather or if the minimum number of travelers isn't reached. If that happens, you're offered another date or a refund.

Prices and times updated yesterday

Good to know

Low physical effortStroller-friendlyPublic transport nearbyInfants must sit on laps

Operated by Jupiter Legend Corporation

Is this one for you?Small groups and families travel together in the same vehicle, so you're not managing the drive or navigating between stops yourself. The fixed itinerary means all three or four Milwaukee stops fit inside a single day from Chicago, with the foliage upgrade available if you're traveling in autumn and want a different route through the region's fall colors instead.

Traveler reviews

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Top questions

Can children come?

Yes. Ticket types: Child (3 to 12 years); Infant (under 3).

What happens if it rains?

It may be canceled due to bad weather. If that happens, you're offered another date or a refund. Free cancellation up to 24 h before the start.

What is the Harley-Davidson Museum like, and how much time do you spend there?

The Harley-Davidson Museum is the world-famous home of the brand's history, and the tour allocates 90 minutes for you to walk through it at your own pace. Admission is at your own cost.

Can you eat lunch during the Milwaukee Public Market stop?

Yes. The Milwaukee Public Market in the historic Third Ward is a food and specialty market where you can buy and eat lunch during the 90-minute stop. Food is at your own expense.

What happens if Miller Brewery is closed on the day of my tour?

If Miller Brewery is closed, the itinerary adjusts to include the Pabst Mansion instead, the estate of the "Beer King," for a 90-minute optional visit. Either way, admission is at your own cost.

What is the foliage season upgrade, and when is it available?

The foliage upgrade is available only during autumn and replaces the Milwaukee city stops with Back Bay Park (60 minutes of maple viewing and hiking along Lake Michigan), Holy Hill Basilica (60 minutes overlooking colorful forests), and Lake Geneva (90 minutes, with an optional lake cruise at your own cost). You choose this option at booking if you're traveling in fall.

Does the tour include admission to attractions, or do you pay separately?

Round-trip transportation and the professional guide are included. Admission to the Harley-Davidson Museum, Miller Brewery, Pabst Mansion and Lake Geneva cruise are at your own cost and not included in the tour price.