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Milwaukee to Windsor (Ontario) drive

(tap on any row to expand for more details)

  Milwaukee
 Mars Cheese Castle
 Chicago
 Saint Joseph (Michigan)
 Kalamazoo
 Ann Arbor
   Windsor (Ontario) 
driving   /   2 days   /   no pets   /   no RV

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Milwaukee to Windsor (Ontario) road trip planner

Here's a sample itinerary for a drive from Milwaukee to Windsor (Ontario). If you're planning a road trip to Windsor (Ontario), you can research locations to stop along the way. Traveling with a dog or cat? View pet-friendly stops between Milwaukee and Windsor (Ontario). Camping along the way? View RV campgrounds between Milwaukee and Windsor (Ontario). Find the best hotels, restaurants, and attractions based on the most talked about places recommended by Trippy members.

customize this trip
 Day 1

11:00 am  start in Milwaukee
drive for about 44 minutes

11:44 am  eat at Mars Cheese Castle
stay for about 1 hour
and leave at 12:44 pm
drive for about 1 hour

1:56 pm  Chicago
stay overnight at The James Chicago Hotel
leave the next day around 10:00 am

day 1 driving ≈ 2 hours
find more stops

 Day 2

10:00 am  leave from The James Chicago Hotel
drive for about 1.5 hours

11:40 am  Saint Joseph (Michigan)
stay for about 1 hour
and leave at 12:40 pm
drive for about 57 minutes

1:37 pm  Kalamazoo
stay for about 1 hour
and leave at 2:37 pm
drive for about 1.5 hours

4:20 pm  Ann Arbor
stay for about 1 hour
and leave at 5:20 pm
drive for about 58 minutes

6:17 pm  arrive in Windsor (Ontario)
eat at Slows Bar-B-Q

day 2 driving ≈ 5.5 hours
find more stops

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Where should I stop along the way?

Mars Cheese Castle  (2 mentions)

Chicago  (306 answers)
    Millennium Park  (54 mentions)
    The Art Institute of Chicago  (48 mentions)
    Shedd Aquarium  (46 mentions)
    Willis Tower  (38 mentions)
    Lincoln Park Zoo  (35 mentions)
    restaurants around Chicago:
        Lou Malnati's Pizzeria
        Pequod's Pizza
        Girl & the Goat
        Big Star
        Au Cheval
    hotels around Chicago:
        The James Chicago Hotel
        Hotel Palomar Chicago
        Acme Hotel Company Chicago
        Virgin Hotels Chicago
        Thompson Chicago
    questions about Chicago:
        What is your favorite restaurant in Chicago?
        Best Chicago pizza?
        What to do in one weekend in Chicago?
        airport transportation
        Chicago - Should we rent a car or no?

Saint Joseph (Michigan)  (2 answers)

Kalamazoo  (11 answers)
    Air Zoo  (2 mentions)
    restaurants around Kalamazoo:
        Bell's Brewery, Inc: Brewery
        Arcadia Brewing Company Kalamazoo
        The Union Cabaret & Grille
        Old Dog Tavern
    questions about Kalamazoo:
        What's the best neighborhood in Kalamazoo for a first time visitor?
        Best free things to do in Kalamazoo?
        What is your favorite restaurant in Kalamazoo?

Ann Arbor  (11 answers)
    Zingerman's Delicatessen  (3 mentions)
    questions about Ann Arbor:
        What's the best neighborhood in Ann Arbor for a first time visitor?
        Ann Arbor: reccomended activities


Where's the best place to eat in Windsor (Ontario)?

Need some recommendations on somewhere to get food?

Trippy members suggest Slows Bar-B-Q, which was mentioned 3 times.

Here are some more restaurants people talk about:




What are some things to do in Windsor (Ontario)?

This section could be endless, so rather than trying to suggest every local activity or attraction, we'll leave it open-ended.

These are some of the places people talk about on Trippy:

Comerica Park  (4 mentions)
Greektown Casino-Hotel  (4 mentions)

Of course, Trippy is the perfect place to ask questions because there's an entire community of travelers talking to each other and sharing tips and advice. Trippy is where you can get answers personalized for your tastes, budgets, trip dates & more!

Click the button below to explore more questions and answers related to Windsor (Ontario).




Do I really have to go back home?

Yes, even this step is optional, because if you're on vacation who wants the trip to end? It's okay, you can start planning your next trip!

Want to plan the trip back? Get the reverse directions for a Windsor (Ontario) to Milwaukee drive, or go to the main page to plan a new road trip.

You can also compare the travel time if you're flying or driving by calculating the distance from Milwaukee to Windsor (Ontario). Or get a full Milwaukee to Windsor (Ontario) flight plan.

Don't forget about exploring your own hometown with a staycation. You can also find some cool day trips or get away for a weekend.

And if you know Milwaukee well, please help your fellow travelers and answer their questions about Milwaukee!





At a Glance
without making any stops
total driving distance is 388 miles
driving time of 5 hours, 54 minutes
Windsor (Ontario) is 1 hour ahead of Milwaukee
32 Milwaukee travel answers
306 Chicago travel answers
2 Saint Joseph (Michigan) travel answers
11 Kalamazoo travel answers
11 Ann Arbor travel answers
10 Windsor (Ontario) travel answers





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