Trippy
 
  Questions  
Drive      Fly      Stay      Login    Signup

Chicago to Cleveland via Ann Arbor

driving   /   2 days   /   no pets   /   no RV

Chicago to Cleveland road trip planner

Here's a sample itinerary for a drive from Chicago to Cleveland. If you're planning a road trip to Cleveland, you can research locations to stop along the way. Make sure you check road conditions to double check the weather. Traveling with a dog or cat? Find pet-friendly stops. Camping along the way? Search for RV campgrounds. 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 Chicago
drive for about 50 minutes

11:50 am  Indiana Dunes State Park (Dunes Nature Preserve)
stay for about 1 hour
and leave at 12:50 pm
drive for about 1 hour

1:50 pm  Benton Harbor
stay for about 1 hour
and leave at 2:50 pm
drive for about 57 minutes

3:47 pm  Kalamazoo
stay overnight and leave the next day around 11:00 am

day 1 driving ≈ 3 hours
find more stops

 Day 2

11:00 am  leave from Kalamazoo
drive for about 1.5 hours

12:42 pm  Ann Arbor
stay for about 1 hour
and leave at 1:42 pm
drive for about 3 hours

4:31 pm  arrive in Cleveland
stay at The Cleveland Hostel

day 2 driving ≈ 4.5 hours
find more stops

drive this trip in  


From:
To:
Depart:
Return:
Get:    
  Change your route
From:
To:
 
  Alternate route
Enter a city to drive through, or find all trips from Chicago to Cleveland.
Via:
 

Chicago to Cleveland questions


Where should I stop along the way?

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

Benton Harbor

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:
        Best free things to do in Kalamazoo?
        What's the best neighborhood in Kalamazoo for a first time visitor?
        What is your favorite restaurant in Kalamazoo?

Ann Arbor  (12 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 stay in Cleveland?

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 Cleveland.

If you're looking for a quick answer, you can check out The Cleveland Hostel, which was mentioned 2 times on Trippy.

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




Where's the best place to eat in Cleveland?

Need some recommendations on somewhere to get food?

Trippy members suggest Lola, which was mentioned 13 times.

Here are some more restaurants people talk about:

Lolita  (6 mentions)
The Greenhouse Tavern  (6 mentions)
Melt Bar & Grilled  (4 mentions)
L'Albatros  (4 mentions)

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




What are some things to do in Cleveland?

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:

West Side Market  (6 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 Cleveland. Click on any question to see answers from the community!

profile  Katie from Columbus asked:
Good restaurants for business dinner?  (10 answers)

profile  Valerie from Los Angeles asked:
What is your favorite restaurant in Cleveland?  (10 answers)

profile  Katie from Los Angeles asked:
What's the best neighborhood in Cleveland for a first time visitor?  (7 answers)

profile  Hayden from Cleveland asked:
New to the city, friend coming to visit: What should we do?  (6 answers)

profile  Kelly from Massachusetts asked:
Fun things to do  (4 answers)

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




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 Cleveland to Chicago 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 Chicago to Cleveland. Or get a full Chicago to Cleveland 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 Chicago well, please help your fellow travelers and answer their questions about Chicago!





At a Glance
without making any stops
total driving distance is 408 miles
driving time of 6 hours, 26 minutes
311 Chicago travel answers
1 Benton Harbor travel answer
11 Kalamazoo travel answers
12 Ann Arbor travel answers
69 Cleveland travel answers





VIEW DETAILED MAP





   
Questions   ·   Destinations   ·   Drive   ·   Fly   ·   Airports   ·   Stay   ·   Search

Login   ·   About   ·   FAQ   ·   Feedback   ·   Privacy   ·   Terms