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Portland to Chicago drive

(tap on any row to expand for more details)

  Portland
 Joseph
 Boise
 Ogden
 Rock Springs
 Cheyenne
 North Platte
 Omaha
 Des Moines
2 travelers   /   driving   /   5 days   /   no pets   /   no RV

City:
Check-in:
Check-out:
Rooms:     Travelers:
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Portland to Chicago road trip planner

Here's a sample itinerary for a drive from Portland 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 Portland and Chicago. Camping along the way? View RV campgrounds between Portland and Chicago. Find the best hotels, restaurants, and attractions based on the most talked about places recommended by Trippy members.

customize this trip
 Day 1

9:00 am  start in Portland
drive for about 6 hours

3:03 pm  Joseph
stay for about 1 hour
and leave at 4:03 pm
drive for about 4 hours

8:03 pm  Boise
stay overnight and leave the next day around 11:00 am

day 1 driving ≈ 10 hours
find more stops

 Day 2

11:00 am  leave from Boise
drive for about 4.5 hours

3:25 pm  Ogden
stay overnight and leave the next day around 10:00 am

day 2 driving ≈ 4.5 hours
find more stops

 Day 3

10:00 am  leave from Ogden
drive for about 2.5 hours

12:41 pm  Rock Springs
stay for about 1 hour
and leave at 1:41 pm
drive for about 3.5 hours

5:21 pm  Cheyenne
stay overnight and leave the next day around 10:00 am

day 3 driving ≈ 6.5 hours
find more stops

 Day 4

10:00 am  leave from Cheyenne
drive for about 3 hours

1:07 pm  North Platte
stay for about 1 hour
and leave at 2:07 pm
drive for about 4 hours

6:08 pm  Omaha
eat at M's Pub
stay overnight and leave the next day around 10:00 am

day 4 driving ≈ 7 hours
find more stops

 Day 5

10:00 am  leave from Omaha
drive for about 2 hours

11:58 am  Des Moines
stay for about 1 hour
and leave at 12:58 pm
drive for about 5 hours

6:01 pm  arrive in Chicago
eat at Lou Malnati's Pizzeria
stay at The James Chicago Hotel

day 5 driving ≈ 7 hours
find more stops

drive this trip in  


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Enter a city to drive through on the way from Portland to Chicago.
Via:
 

Where does my trip begin?

Your starting point is Portland, Oregon.

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?

Joseph  (2 answers)

Boise  (24 answers)
    Idaho State Capitol Building  (2 mentions)
    questions about Boise:
        Have a free day in Boise next week, any recommendations on what to do?
        What do you do and where to eat in Boise, ID?
        Best free things to do in Boise?

Ogden  (3 answers)

Rock Springs  (2 answers)

Cheyenne  (13 answers)
    questions about Cheyenne:
        Driving from Kennesaw ga to Cheyenne wy
        What are some "must see" places in Cheyenne.

North Platte  (2 answers)

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:
        M's Pub
        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?
        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?


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!

profile  Sunil from Mountain View asked:
Best Chicago pizza?  (18 answers)

profile  Katie from Los Angeles asked:
What is your favorite restaurant in Chicago?  (15 answers)

profile  Blair from Halifax asked:
What to do in one weekend in Chicago?  (14 answers)

profile  지은 from asked:
airport transportation  (14 answers)

profile  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.




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





At a Glance
without making any stops
total driving distance is 2,119 miles
driving time of 30 hours, 53 minutes
Chicago is 2 hours ahead of Portland
219 Portland travel answers
2 Joseph travel answers
24 Boise travel answers
3 Ogden travel answers
2 Rock Springs travel answers
13 Cheyenne travel answers
2 North Platte travel answers
17 Omaha travel answers
18 Des Moines travel answers
278 Chicago travel answers





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