Here's a sample itinerary for a drive from Washington, DC 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 Washington, DC and Chicago. Find the best hotels, restaurants, and attractions based on the most talked about places recommended by Trippy members.
Your starting point is Washington, District of Columbia.
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.
Harpers Ferry (3 answers)
Pittsburgh (30 answers)
Andy Warhol Museum (9 mentions)
Carnegie Museum of Natural History (8 mentions)
National Aviary (6 mentions)
Carnegie Museum of Art (6 mentions)
Phipps Conservatory (5 mentions)
restaurants around Pittsburgh:
questions about Pittsburgh:
First timer to Pittsburgh, what should I explore?
First time to Pittsburgh, what are things a first time visitor has to do?
Parking spots for a 45' motorcoach in or near downtown Pittsburgh
Pittsburgh on a budget?
Trendy neighborhoods in Pittsburgh?
Canton (Ohio) (3 answers)
Pro Football Hall of Fame (2 mentions)
questions about Canton (Ohio):
What is your favorite restaurant in Canton (Ohio)?
Cleveland (44 answers)
Rock and Roll Hall of Fame and Museum (13 mentions)
The Cleveland Museum of Art (12 mentions)
Rock and Roll Hall of Fame and Museum (6 mentions)
West Side Market (6 mentions)
Great Lakes Brewing Company (5 mentions)
restaurants around Cleveland:
The Greenhouse Tavern
Melt Bar & Grilled
questions about Cleveland:
Good restaurants for business dinner?
What is your favorite restaurant in Cleveland?
New to the city, friend coming to visit: What should we do?
Vegetarian near Playhouse Square
Best breweries in Cleveland?
Toledo (Ohio) (8 answers)
Toledo Zoo (2 mentions)
questions about Toledo (Ohio):
Where's a fun place for breakfast in Toledo Ohio?
Indiana Dunes State Park (Dunes Nature Preserve) (4 mentions)
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!
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!
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 Washington, DC well, please help your fellow travelers and answer their questions about Washington, DC!