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Detroit to Chicago drive

(tap on any row to expand for more details)

  Detroit
 Ann Arbor
 Marshall (Michigan)
 Kalamazoo
 Saint Joseph (Michigan)
 Indiana Dunes State Park (Dunes Nature Preserve)
   Chicago 
driving   /   2 days   /   no pets   /   no RV

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Detroit to Chicago road trip planner

Here's a sample itinerary for a drive from Detroit to Chicago. If you're planning a road trip to Chicago, you can research locations to stop along the way. Traveling with a dog or cat? View pet-friendly stops between Detroit and Chicago. Camping along the way? View RV campgrounds between Detroit and Chicago. 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 Detroit
drive for about 43 minutes

11:43 am  Ann Arbor
stay for about 1 hour
and leave at 12:43 pm
drive for about 1 hour

1:53 pm  Marshall (Michigan)
stay for about 1 hour
and leave at 2:53 pm
drive for about 41 minutes

3:33 pm  Kalamazoo
stay overnight and leave the next day around 11:00 am

day 1 driving ≈ 2.5 hours
find more stops

 Day 2

11:00 am  leave from Kalamazoo
drive for about 57 minutes

11:57 am  Saint Joseph (Michigan)
stay for about 1 hour
and leave at 12:57 pm
drive for about 56 minutes

1:54 pm  Indiana Dunes State Park (Dunes Nature Preserve)
stay for about 1 hour
and leave at 2:54 pm
drive for about 50 minutes

3:43 pm  arrive in Chicago
stay at The James Chicago Hotel

day 2 driving ≈ 2.5 hours
find more stops

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Where should I stop along the way?

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

Marshall (Michigan)  (2 answers)

Kalamazoo  (9 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?

Saint Joseph (Michigan)  (2 answers)

Indiana Dunes State Park (Dunes Nature Preserve)  (4 mentions)


Where's the best place to stay in Chicago?

Are you going straight to a hotel, or looking for a vacation rental or Airbnb?

The best resource on neighborhoods, areas, and hotels is the Trippy page on where to stay in Chicago.

You can also see most people recommend as the best amount of time to visit. Find out how many days in Chicago to stay.

If you're looking for a quick answer, you can check out The James Chicago Hotel, which was mentioned 12 times on Trippy.

Here are some more hotels people talk about:

Hotel Palomar Chicago  (9 mentions)
Virgin Hotels Chicago  (8 mentions)
Thompson Chicago  (6 mentions)

Want to research more popular hotels in Chicago? Click the blue button below.




Where's the best place to eat in Chicago?

Need some recommendations on somewhere to get food?

Trippy members suggest Lou Malnati's Pizzeria, which was mentioned 36 times.

Here are some more restaurants people talk about:

Pequod's Pizza  (26 mentions)
Girl & the Goat  (24 mentions)
Big Star  (23 mentions)
Au Cheval  (17 mentions)

Want to research more popular restaurants in Chicago? Click the blue button below.




What are some things to do in Chicago?

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:

Millennium Park  (54 mentions)
Shedd Aquarium  (46 mentions)
Willis Tower  (38 mentions)
Lincoln Park Zoo  (35 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!

For example, here are some questions people have asked about Chicago. Click on any question to see answers from the community!

profile  Katie from Los Angeles asked:
What is your favorite restaurant in Chicago?  (24 answers)

profile  Sunil from Mountain View asked:
Best Chicago pizza?  (18 answers)

profile  Blair from Halifax asked:
What to do in one weekend in Chicago?  (14 answers)

profile  지은 from asked:
airport transportation  (14 answers)

profile  Stacey from Jackson, Mississippi asked:
What are the coolest hotels in downtown Chicago?  (12 answers)

Click the button below to explore more questions and answers related to Chicago.




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 Chicago to Detroit drive, or go to the main page to plan a new road trip.

Looking for ideas for more destinations within driving distance of Detroit? Try searching for places within 4 hours of Detroit.

You can also compare the travel time if you're flying or driving by calculating the distance from Detroit to Chicago. Or get a full Detroit to Chicago 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. Maybe try typing in a faraway location like London, Hong Kong, or Sydney, and get inspired for your dream trip around the world.

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





At a Glance
without making any stops
total driving distance is 281 miles
driving time of 4 hours, 17 minutes
Chicago is 1 hour behind Detroit
27 Detroit travel answers
11 Ann Arbor travel answers
2 Marshall (Michigan) travel answers
9 Kalamazoo travel answers
2 Saint Joseph (Michigan) travel answers
289 Chicago travel answers





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