The 8 Best Day Trips from Milwaukee
How far each place is, what to see there, and a plan for the day.
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There are 8 good day trips from Milwaukee, United States, led by Chicago, Kenosha, Waukegan. The closest is Waukesha, about 40 min by car, and 2 of them fit into half a day. Below: drive times, distances, what to see, and a sample day plan.
Built from 8 nearby places, with sights from real traveler trips, on Packy AI. Last updated November 2026 by the Packy AI Travel Team.
Day trips from Milwaukee
- 1
Chicago, United States
Full-day tripAbout 2 hr 5 min by car134 km south of MilwaukeeKnown for 360 Chicago.
- 2
Kenosha, United States
Half-day tripAbout 1 hr by car51 km south of Milwaukee - 3
Waukegan, United States
Full-day tripAbout 1 hr 25 min by car75 km south of Milwaukee - 4
Evanston, United States
Full-day tripAbout 1 hr 45 min by car112 km south of Milwaukee - 5
Schaumburg, United States
Full-day tripAbout 1 hr 45 min by car113 km south of Milwaukee - 6
Bolingbrook, United States
Long day or overnightAbout 2 hr 20 min by car150 km south of Milwaukee - 7
West Ridge, United States
Full-day tripAbout 1 hr 50 min by car117 km south of Milwaukee - 8
Waukesha, United States
Half-day tripAbout 40 min by car27 km west of Milwaukee
A sample day: Milwaukee to Chicago
- 07:30Leave Milwaukee
- 09:35Arrive in Chicago (2 hr 5 min drive)
- 09:50360 Chicago
- 11:50Lunch
- 13:05Explore the old town, markets and cafes of Chicago
- 15:35Head back to Milwaukee
- 17:40Home in Milwaukee
Good to know
Frequently asked questions
- What are the best day trips from Milwaukee?
- The best day trips from Milwaukee are Chicago, Kenosha, Waukegan, Evanston, Schaumburg. The closest is Waukesha, about 40 min away by car.
- What is the closest day trip from Milwaukee?
- Waukesha is the closest, 27 km west of Milwaukee, roughly 40 min by car. Best as a half-day trip.
- Where can I go within an hour of Milwaukee?
- 2 places are within about an hour's drive of Milwaukee: Waukesha (40 min), Kenosha (1 hr).
- What is the biggest city near Milwaukee for a day out?
- Chicago is the largest city in day-trip range, 134 km south of Milwaukee and about 2 hr 5 min by car. With that much to see, start early or stay the night.
- Where can I go for a weekend from Milwaukee?
- For a weekend away from Milwaukee, pick the places far enough to be worth a night: Bolingbrook (150 km, 2 hr 20 min), Chicago (134 km, 2 hr 5 min), West Ridge (117 km, 1 hr 50 min), Schaumburg (113 km, 1 hr 45 min). Closer places on this list work better as a single day.
- How far is too far for a day trip from Milwaukee?
- Up to about two hours each way keeps the day relaxed. The farthest place on this list is Bolingbrook at 150 km, around 2 hr 20 min by car, which is better as a long day or an overnight stay.
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