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Portland to Philadelphia via Chicago

(tap on any row to expand for more details)

  Portland
 Boise
 Laramie
 Omaha
 Chicago
 Cleveland
driving   /   6 days   /   no pets   /   no RV

City:
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Portland to Philadelphia road trip planner

Here's a sample itinerary for a drive from Portland to Philadelphia. If you're planning a road trip to Philadelphia, 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

10:00 am  start in Portland
drive for about 7 hours

4:55 pm  Boise
stay overnight and leave the next day around 10:00 am

day 1 driving ≈ 7 hours
find more stops

 Day 2

10:00 am  leave from Boise
drive for about 10 hours

7:46 pm  Laramie
stay overnight and leave the next day around 10:00 am

day 2 driving ≈ 10 hours
find more stops

 Day 3

10:00 am  leave from Laramie
drive for about 7.5 hours

5:43 pm  Omaha
eat at M's Pub
stay overnight and leave the next day around 10:00 am

day 3 driving ≈ 7.5 hours
find more stops

 Day 4

10:00 am  leave from Omaha
drive for about 7 hours

5:01 pm  Chicago
eat at Lou Malnati's Pizzeria
stay overnight at The James Chicago Hotel
leave the next day around 11:00 am

day 4 driving ≈ 7 hours
find more stops

 Day 5

11:00 am  leave from The James Chicago Hotel
drive for about 5.5 hours

4:33 pm  Cleveland
stay overnight at The Cleveland Hostel
leave the next day around 10:00 am

day 5 driving ≈ 5.5 hours
find more stops

 Day 6

10:00 am  leave from The Cleveland Hostel
drive for about 6.5 hours

4:34 pm  arrive in Philadelphia
stay at Loews Hotel Philadelphia

day 6 driving ≈ 6.5 hours
find more stops

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Where should I stop along the way?

Boise  (29 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?

Laramie  (6 answers)
    questions about Laramie:
        What is your favorite restaurant in Laramie?

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

Chicago  (289 answers)
    Millennium Park  (54 mentions)
    The Art Institute of Chicago  (48 mentions)
    Shedd Aquarium  (46 mentions)
    Willis Tower  (38 mentions)
    Lincoln Park Zoo  (35 mentions)
    restaurants around Chicago:
        Lou Malnati's Pizzeria
        Pequod's Pizza
        Girl & the Goat
        Big Star
        Au Cheval
    hotels around Chicago:
        The James Chicago Hotel
        Hotel Palomar Chicago
        Acme Hotel Company Chicago
        Virgin Hotels Chicago
        Thompson Chicago
    questions about Chicago:
        What is your favorite restaurant in Chicago?
        Best Chicago pizza?
        What to do in one weekend in Chicago?
        airport transportation
        What are the coolest hotels in downtown Chicago?

Cleveland  (54 answers)
    Rock and Roll Hall of Fame and Museum  (13 mentions)
    The Cleveland Museum of Art  (12 mentions)
    Rock and Roll Hall of Fame and Museum  (6 mentions)
    West Side Market  (6 mentions)
    Great Lakes Brewing Company  (5 mentions)
    restaurants around Cleveland:
        Lola
        Lolita
        The Greenhouse Tavern
        Melt Bar & Grilled
        L'Albatros
    hotels around Cleveland:
        The Cleveland Hostel
    questions about Cleveland:
        Good restaurants for business dinner?
        What is your favorite restaurant in Cleveland?
        New to the city, friend coming to visit: What should we do?
        What's the best neighborhood in Cleveland for a first time visitor?
        Fun things to do


Where's the best place to stay in Philadelphia?

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 Philadelphia.

If you're looking for a quick answer, you can check out Loews Hotel Philadelphia, which was mentioned 2 times on Trippy.

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




Where's the best place to eat in Philadelphia?

Need some recommendations on somewhere to get food?

Trippy members suggest Reading Terminal Market, which was mentioned 24 times.

Here are some more restaurants people talk about:

Jim's Steaks  (20 mentions)
Pat's King of Steaks  (11 mentions)
Geno's Steaks  (8 mentions)
Zahav  (6 mentions)

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




What are some things to do in Philadelphia?

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:

The Liberty Bell  (12 mentions)
Independence Mall  (7 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 Philadelphia. Click on any question to see answers from the community!

profile  Hannah from Milwaukee asked:
What is there to do in Philly besides eat cheese steaks?  (14 answers)

profile  Scott from Chicago asked:
Pat's or Geno's: Which has the better cheesesteak?  (13 answers)

profile  Katie from Los Angeles asked:
What is your favorite restaurant in Philadelphia?  (12 answers)

profile  Sharon from West Los Angeles asked:
Anybody know of great gems in the city I can dine at during my stay?  (9 answers)

profile  teri from Atlanta asked:
Eating out on a budget.  (9 answers)

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




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 Philadelphia 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 Philadelphia. Or get a full Portland to Philadelphia 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 2,877 miles
driving time of 42 hours, 27 minutes
227 Portland travel answers
29 Boise travel answers
6 Laramie travel answers
24 Omaha travel answers
289 Chicago travel answers
54 Cleveland travel answers
108 Philadelphia travel answers





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