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Chicago to Portland drive

driving   /   5 days   /   no pets   /   no RV

Chicago to Portland road trip planner

Here's a sample itinerary for a drive from Chicago to Portland. If you're planning a road trip to Portland, you can research locations to stop along the way. Make sure you check road conditions to double check the weather. Traveling with a dog or cat? Find pet-friendly stops. Camping along the way? Search for RV campgrounds. Find the best hotels, restaurants, and attractions based on the most talked about places recommended by Trippy members.

customize this trip
 Day 1

10:00 am  start in Chicago
drive for about 5 hours

3:15 pm  Des Moines
stay for about 1 hour
and leave at 4:15 pm
drive for about 2 hours

6:23 pm  Omaha
eat at M's Pub
stay overnight and leave the next day around 11:00 am

day 1 driving ≈ 7.5 hours
find more stops

 Day 2

11:00 am  leave from Omaha
drive for about 4 hours

3:00 pm  North Platte
stay overnight and leave the next day around 10:00 am

day 2 driving ≈ 4 hours
find more stops

 Day 3

10:00 am  leave from North Platte
drive for about 3.5 hours

1:28 pm  Cheyenne
stay for about 1 hour
and leave at 2:28 pm
drive for about 3.5 hours

6:07 pm  Rock Springs (Wyoming)
stay overnight and leave the next day around 10:00 am

day 3 driving ≈ 7 hours
find more stops

 Day 4

10:00 am  leave from Rock Springs (Wyoming)
drive for about 2.5 hours

12:40 pm  Ogden
stay for about 1 hour
and leave at 1:40 pm
drive for about 4.5 hours

6:05 pm  Boise
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 Boise
drive for about 7 hours

4:55 pm  arrive in Portland
stay at Ace Hotel Portland

day 5 driving ≈ 7 hours
find more stops

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Chicago to Portland questions

profile  Deborah asked:
Pet friendly stops  (0 answers)


Where should I stop along the way?

Des Moines  (21 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?

Omaha  (24 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
        TT Best Free Overnight

North Platte  (3 answers)

Cheyenne  (14 answers)
    questions about Cheyenne:
        Driving from Kennesaw ga to Cheyenne wy
        What are some "must see" places in Cheyenne.

Rock Springs (Wyoming)  (5 answers)

Ogden  (5 answers)

Boise  (36 answers)
    Idaho State Capitol Building  (2 mentions)
    questions about Boise:
        Best free things to do in Boise?
        What do you do and where to eat in Boise, ID?


Where's the best place to stay in Portland?

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 Portland.

If you're looking for a quick answer, you can check out Ace Hotel Portland, which was mentioned 8 times on Trippy.

Here are some more hotels people talk about:

The Nines, Portland  (7 mentions)
Hotel Monaco Portland  (4 mentions)
The Heathman Hotel  (3 mentions)

Want to research more popular hotels in Portland? Click the blue button below.




Where's the best place to eat in Portland?

Need some recommendations on somewhere to get food?

Trippy members suggest Voodoo Doughnuts, which was mentioned 27 times.

Here are some more restaurants people talk about:

Tasty N Sons  (11 mentions)
Lardo  (10 mentions)
Potato Champion  (9 mentions)
Pok Pok Restaurant  (9 mentions)

Want to research more popular restaurants in Portland? Click the blue button below.




What are some things to do in Portland?

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:

Powell's City of Books  (17 mentions)
Japanese Gardens  (15 mentions)
Portland Saturday Market  (13 mentions)
Timberline Lodge  (12 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 Portland. Click on any question to see answers from the community!

profile  Katie from Los Angeles asked:
What is your favorite restaurant in Portland?  (28 answers)

profile  Matt from Atlanta asked:
Mid July: 1 week with wife and kid - what should we prioritize?  (12 answers)

profile  Beverly from San Luis Obispo asked:
Best coffee shops in Portland  (10 answers)

profile  Beth from Maryland asked:
Visiting in July for 5 days with my boyfriend, where and what must we do?  (9 answers)

profile  Marilyn from Vancouver asked:
Artsy area with fun little shops  (8 answers)

Click the button below to explore more questions and answers related to Portland.




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





At a Glance
without making any stops
total driving distance is 2,119 miles
driving time of 30 hours, 53 minutes
Portland is 2 hours behind Chicago
328 Chicago travel answers
21 Des Moines travel answers
24 Omaha travel answers
3 North Platte travel answers
14 Cheyenne travel answers
5 Rock Springs (Wyoming) travel answers
5 Ogden travel answers
36 Boise travel answers
246 Portland travel answers





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