Here's a sample itinerary for a drive from Jackson (Wyoming) 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.
Your starting point is Jackson, Wyoming.
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.
Lander (3 answers)
questions about Lander:
Fishing in Lander, Wyoming
Laramie (5 answers)
questions about Laramie:
What is your favorite restaurant in Laramie?
Original Pony Express Station
Hastings (Nebraska) (2 answers)
questions about Hastings (Nebraska):
Places to go
Omaha (17 answers)
Henry Doorly Zoo (8 mentions)
Joslyn Art Museum (3 mentions)
Lauritzen Gardens (2 mentions)
The Durham Museum (2 mentions)
Omaha Children's Museum (2 mentions)
restaurants around Omaha:
Stokes Grill & Bar Wood Fired Foods
801 Chophouse at The Paxton
Lo Sole Mio Ristorante
questions about Omaha:
Best free things to do in Omaha?
Low-key bachelor party activities in Omaha?
Dog friendly hotels
Des Moines (18 answers)
questions about Des Moines:
What's the best neighborhood in Des Moines for a first time visitor?
Any good hiking spots in or near Des Moines?
University of Iowa (7 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 Jackson (Wyoming) well, please help your fellow travelers and answer their questions about Jackson (Wyoming)!