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Ashburn (Virginia) to Chicago drive

2 travelers   /   driving   /   2 days



Ashburn (Virginia) to Chicago road trip planner

Here's a sample itinerary for a drive from Ashburn (Virginia) 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.

customize this trip
 Day 1

10:00 am  start in Ashburn (Virginia)
drive for about 2.5 hours

12:33 pm  Fallingwater
stay for about 1 hour and leave at 1:33 pm
drive for about 1 hour

2:36 pm  Pittsburgh
stay for about 1 hour and leave at 3:36 pm
drive for about 2 hours

5:39 pm  Canton (Ohio)
stay for about 1 hour and leave at 6:39 pm
drive for about 1 hour

7:45 pm  Rock and Roll Hall of Fame and Museum
stay overnight and leave the next day around 10:00 am

day 1 driving ≈ 6.5 hours

 Day 2

10:00 am  leave from Rock and Roll Hall of Fame and Museum
drive for about 2 hours

12:03 pm  Toledo (Ohio)
stay for about 1 hour and leave at 1:03 pm
drive for about 2 hours

3:13 pm  Middlebury (Indiana)
stay for about 1 hour and leave at 4:13 pm
drive for about 2 hours

6:24 pm  arrive in Chicago
eat at Lou Malnati's Pizzeria
stay at The James Chicago Hotel

day 2 driving ≈ 6.5 hours

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Enter a city to drive through on the way from Ashburn (Virginia) to Chicago.
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Where does my trip begin?

Your starting point is Ashburn, Virginia.

You can enter an exact street address if you want to get precise directions, but this is optional.




How many cars do we need?

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.




Where should I stop along the way?

Fallingwater  (7 mentions)
Pittsburgh  (29 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:
        Primanti Brothers
        Primanti Bros.
    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)?
        Rayne
Rock and Roll Hall of Fame and Museum  (19 mentions)
Toledo (Ohio)  (6 answers)
    Toledo Zoo  (2 mentions)
Middlebury (Indiana)




Where does my trip end?

Your final destination is Chicago, Illinois.

You can enter the exact street address of your destination, but this is optional.




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!

 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.






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






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At a Glance
without making any stops
total driving distance is 685 miles
driving time of 10 hours, 57 minutes
Chicago is 1 hour behind Ashburn (Virginia)
29 Pittsburgh travel answers
3 Canton (Ohio) travel answers
6 Toledo (Ohio) travel answers
1 Middlebury (Indiana) travel answer
258 Chicago travel answers





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