Cheap flights from Portland to Chicago

Round-trip
Economy
Portland (PDX)
Chicago (CHI)
Thu 2/18
Thu 2/25
Any month
Compare vs. momondo |

Flight information for Portland to Chicago
(PDX to CHI)

Find info about flight duration, direct flights, and airports for your flight from Portland to Chicago
Best Price Found $92 The best flight deal from Portland to Chicago found on momondo in the last 72 hours is $92
Fastest flight time 3h 52m The fastest flight from Portland to Chicago takes 3h 52m.
Direct flights We Direct flights go from Portland to Chicago on Wednesday. Airlines offering direct flights are: LOT and United Airlines..
Airports in Chicago 3 airports There are 3 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW), Chicago Greater Rockford (RFD)

How to get the cheapest flight ticket from Portland to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the cheapest month to fly from Portland to Chicago?
August
The cheapest time of year to fly to Chicago from Portland is August. Most expensive is December
What is the cheapest day to depart Portland for Chicago?
Friday
The cheapest day of the week is typically Friday. The most expensive is typically Sunday
When is the cheapest time to fly from Portland to Chicago?
in the afternoon
Portland to Chicago flights are approximately 15% more expensive in the morning than in the afternoon
What is the cheapest airline that flies to Chicago from Portland?
Frontier
Frontier, Sun Country Air, and Spirit Airlines are the most popular carriers operating from Portland to Chicago
What is the cheapest Portland to Chicago flight route?
Portland - Chicago O'Hare Intl
Fly from Portland to Chicago O'Hare Intl for the best Portland - Chicago flight prices
How far in advance should you book Portland to Chicago flights?
19 days before
The cheapest time to buy a flight from Portland to Chicago is approximately 19 days to departure
60
Days before departure
0

Easily compare round-trip flights from Portland to Chicago

Below you can see the best fares for your round-trip flight route over the next three months. All fares were found on momondo this week. Browse the quickest and cheapest flights from Portland to Chicago by changing tabs
Multiple Airlines
Feb 18
7h 45m
Portland
7h 45m
1 stop
11:00 pm
Chicago O'Hare Intl
Feb 23
4:00 am
Chicago O'Hare Intl
4h 25m
8:25 am
Portland
Multiple Airlines
Feb 25
7h 45m
Portland
7h 45m
1 stop
11:00 pm
Chicago O'Hare Intl
Mar 1
5:30 am
Chicago O'Hare Intl
9h 16m
1 stop
2:46 pm
Portland
Multiple Airlines
Feb 18
7h 45m
Portland
7h 45m
1 stop
11:00 pm
Chicago O'Hare Intl
Feb 22
5:30 am
Chicago O'Hare Intl
9h 16m
1 stop
2:46 pm
Portland

Find the cheapest one-way flights from Portland to Chicago

If you're looking for one-way flights from Portland to Chicago, view some of our deals below provided by Frontier
Multiple Airlines
Feb 10
7h 17m
Portland
7h 17m
1 stop
1:12 pm
Chicago O'Hare Intl
Frontier
Jan 31
8h 19m
Portland
8h 19m
1 stop
11:31 pm
Chicago O'Hare Intl
Spirit Airlines
Jan 27
10h 09m
Portland
10h 09m
1 stop
3:49 pm
Chicago O'Hare Intl

Best airlines flying from Portland to Chicago

Compare and see reviews for airlines that fly from Portland to Chicago with momondo
AirlineRatingFree CancellationPrice
Frontier
PriceFrom $106
Free Cancellation
Rating
5.7
6.4

Boarding

5.4

Comfort

6.8

Crew

4.6

Entertainment

4.7

Food

Reviews

Pros: That we did not crash and I did not die! PTL

Cons: You pay for everything on a menu style way. Peanuts, soda, luggage and seat choice all extras. Then we got to Denver and they lost about 10 peoples' luggage. They could not find it for 45 minutes and then I found it on the wrong carousel going round and round! Very dissatisfied with the luggage mess in Denver on flight 802 September 10!

1 / 10
Spirit Airlines
PriceFrom $116
Free Cancellation
Rating
5.6
6.1

Boarding

5.4

Comfort

6.5

Crew

4.6

Entertainment

4.7

Food

Reviews

Pros: Very prompt, even early flights!

Cons: The spirit terminals are very chaotic. Attendants are very good, though.

1 / 10
Delta
PriceFrom $139
Free Cancellation
Rating
7.9
8.1

Boarding

7.8

Comfort

8.5

Crew

7.8

Entertainment

7.5

Food

Reviews

Pros: Went very smoothly. Very comfortable.

Cons: Can't think of anything.

1 / 10
American Airlines
PriceFrom $140
Free Cancellation
Rating
7.2
7.5

Boarding

7.1

Comfort

7.8

Crew

6.8

Entertainment

6.7

Food

Reviews

Pros: Crew

Cons: Decaf tea

1 / 10
Alaska Airlines
PriceFrom $140
Free Cancellation
Rating
8.3
8.5

Boarding

8.3

Comfort

8.8

Crew

7.9

Entertainment

7.9

Food

Reviews

Cons: Seems like the complete lack of beverages due to covid is a little overkill. Most of the items were single serving anyway so doing away with them doesnt feel like mitigating anything more than an additional expense for the company. Not a huge deal though in light of the other losses the industry is reeling from while trying to adjust

1 / 10
United Airlines
PriceFrom $140
Free Cancellation
Rating
7.0
7.4

Boarding

6.9

Comfort

7.7

Crew

6.5

Entertainment

6.4

Food

Reviews

Cons: Bad smell

1 / 10
Sun Country Air
PriceFrom $141
Free Cancellation
Rating
7.7
8.1

Boarding

7.6

Comfort

8.4

Crew

6.8

Entertainment

7.0

Food

Reviews

Cons: Less time on the tarmac. Spent at least 40 min, 20 each side just sitting.

1 / 10
Southwest
PriceFrom $374
Free Cancellation
Rating
8.4
8.7

Boarding

8.4

Comfort

9.0

Crew

8.0

Entertainment

7.8

Food

Reviews

Pros: Southwest's humane baggage policy and reasonable legroom make them among the best airlines.

Cons: Families should be permitted to sit together, even if, for example, security takes 40 solid minutes (computed tomography machines are sloooow). Crew did not help at all so all three of us were separated.

1 / 10

Which airlines flying from Portland to Chicago have COVID-19 safety policies in place?

Airlines such as Alaska Airlines and Delta have taken additional precautions to make sure you’re safer while traveling. When flying from Portland to Chicago, expect masks to be provided - they are required onboard. Aircrafts are also being cleaned thoroughly with enhanced products regularly. Additional policies include the installation of HEPA filters and pre-flight testing. Some airlines are even offering socially-distanced seating for a limited time. Keep in mind that policies will vary by airline.

Are airlines flying from Portland to Chicago offering flexible cancellation due to COVID-19?

To ease the stress of booking flights, some of our airline partners flying from Portland to Chicago are responding to the global pandemic. The following airlines may have a flexible cancellation policy to help accommodate travelers: United Airlines, Alaska Airlines, and American Airlines.


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