Here's a sample itinerary for a drive from Chesterfield (Missouri) 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 Chesterfield (Missouri) and Chicago. Find the best hotels, restaurants, and attractions based on the most talked about places recommended by Trippy members.
11:00 am start in Chesterfield (Missouri)
drive for about 1 hour
12:11 pm Old 66
stay for about 1 hour and leave at 1:11 pm
drive for about 1 hour
2:22 pm Springfield (Illinois)
stay for about 1 hour and leave at 3:22 pm
drive for about 1 hour
4:26 pm Bloomington (Illinois)
stay overnight and leave the next day around 11:00 am
day 1 driving ≈ 3.5 hours
11:00 am leave from Bloomington (Illinois)
drive for about 37 minutes
11:37 am Pontiac
stay for about 1 hour and leave at 12:37 pm
drive for about 1.5 hours
2:05 pm Naperville
stay for about 1 hour and leave at 3:05 pm
drive for about 37 minutes
3:42 pm arrive in Chicago
stay at The James Chicago Hotel
day 2 driving ≈ 2.5 hours
Your starting point is Chesterfield, Missouri.
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.
Old 66 (2 mentions)
questions about Old 66:
Motels to stay overnight
Springfield (Illinois) (10 answers)
Bloomington (Illinois) (4 answers)
questions about Bloomington (Illinois):
Inexpensive things for 4
Best free things to do in Bloomington (Illinois)?
Pontiac
Naperville (2 answers)
Garfield Park Conservatory (4 mentions)
questions about Naperville:
What is your favorite restaurant in Naperville?
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 from Mountain View asked:
Best Chicago pizza? (18 answers)
Katie from Los Angeles asked:
What is your favorite restaurant in Chicago? (15 answers)
Blair from Halifax asked:
What to do in one weekend in Chicago? (14 answers)
지은 from asked:
airport transportation (14 answers)
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.
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 Chesterfield (Missouri) 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 Chesterfield (Missouri) to Chicago. Or get a full Chesterfield (Missouri) 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 Chesterfield (Missouri) well, please help your fellow travelers and answer their questions about Chesterfield (Missouri)!
