Here's a sample itinerary for a drive from Cleveland to Chicago. If you're planning a road trip to Chicago, you can research locations to stop along the way. Find the best restaurants, hotels, and attractions based on the most talked about places recommended by Trippy members.
9:00 am start in Cleveland
drive for about 1 hour
10:12 am Cedar Point
stay for about 1 hour and leave at 11:12 am
drive for about 1 hour
12:19 pm Toledo (Ohio)
stay for about 1 hour and leave at 1:19 pm
drive for about 1 hour
2:27 pm Holiday City
stay for about 1 hour and leave at 3:27 pm
drive for about 1.5 hours
4:47 pm Middlebury (Indiana)
stay for about 1 hour and leave at 5:47 pm
drive for about 1.5 hours
7:20 pm Indiana Dunes National Lakeshore
stay for about 1 hour and leave at 8:20 pm
drive for about 49 minutes
9:09 pm arrive in Chicago
stay at The James Chicago Hotel
driving ≈ 7 hours
Stephanie Parkhill from Ottawa asked:
Can't decide! What's a better place to visit, Cleveland or Chicago? (17 answers)
Your starting point is Cleveland, Ohio.
You can enter an exact street address if you want to get precise directions, but this is optional.
Since there are only 2 travelers, we assume you're driving 1 car. You can adjust the number of people traveling at the top. We assume a maximum of 4 passengers per car, but you can change the number of cars to fit your situation.
Cedar Point (5 mentions)
Toledo (Ohio) (8 answers)
Toledo Zoo (2 mentions)
questions about Toledo (Ohio):
Where's a fun place for breakfast in Toledo Ohio?
Holiday City
Middlebury (Indiana)
Indiana Dunes National Lakeshore
Your final destination is Chicago, Illinois.
You can enter the exact street address of your destination, but this is optional.
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:
Want to research more popular hotels in Chicago? Click the blue button below.
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:
Want to research more popular restaurants in Chicago? Click the blue button below.
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:
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!
Sunil Gupta from Mountain View asked:
Best Chicago pizza? (18 answers)
Katie Simons from Los Angeles asked:
What is your favorite restaurant in Chicago? (15 answers)
Blair Cabot from Halifax asked:
What to do in one weekend in Chicago? (14 answers)
지은 기 from asked:
airport transportation (14 answers)
Stacey Wall 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.
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 Cleveland 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 Cleveland to Chicago. Or get a full Cleveland 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 Cleveland well, please help your fellow travelers and answer their questions about Cleveland!
