Cheap flights from Portland to Chicago

Round-trip
Economy
Portland (PDX)
Chicago (CHI)
Tue 7/13
Tue 7/20
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$221The best flight deal from Portland to Chicago found on momondo in the last 72 hours is $221
Fastest flight time3h 53mThe fastest flight from Portland to Chicago takes 3h 53m
Direct flightsMo and WeDirect flights go from Portland to Chicago on Monday and Wednesday. The only airline offering direct flights is United Airlines.
Airports in Chicago3 airportsThere 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 18% more expensive at noon 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
Jul 7
PDX7:55 pmPortland
4h 20m
ORD12:15 amChicago O'Hare Intl
Jul 24
ORD8:59 amChicago O'Hare Intl
7h 15m
1 stop
PDX4:14 pmPortland
Multiple Airlines
Jul 13
PDX6:50 amPortland
10h 53m
1 stop
ORD5:43 pmChicago O'Hare Intl
Jul 20
ORD3:55 pmChicago O'Hare Intl
4h 28m
PDX8:23 pmPortland
Multiple Airlines
Jul 13
PDX6:50 amPortland
10h 53m
1 stop
ORD5:43 pmChicago O'Hare Intl
Jul 21
ORD3:55 pmChicago O'Hare Intl
4h 28m
PDX8:23 pmPortland

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
United Airlines
Oct 6
PDX9:00 amPortland
3h 44m
ORD12:44 pmChicago O'Hare Intl
United Airlines
Sep 7
PDX12:30 pmPortland
6h 00m
1 stop
ORD6:30 pmChicago O'Hare Intl
Delta
Sep 15
PDX4:15 amPortland
6h 47m
1 stop
MDW11:02 amChicago Midway

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
7.5
8.1

Boarding

7.0

Comfort

8.2

Crew

6.8

Entertainment

7.1

Food

Reviews

Pros: Seat was spacious. Crew very accommodating.

Cons: Lines for bag check very long.

1 / 10
Spirit Airlines
PriceFrom $116
Free Cancellation
Rating
7.1
7.4

Boarding

6.8

Comfort

7.7

Crew

6.3

Entertainment

6.5

Food

Reviews

Pros: Well, it was not very comfortable and we were delayed for an hour. And a crew member was sick.

Cons: Mostly everything.

1 / 10
Delta
PriceFrom $139
Free Cancellation
Rating
8.1
8.3

Boarding

8.4

Comfort

8.3

Crew

7.9

Entertainment

8.1

Food

Reviews

Cons: Wouldn't let us on the flight when there was plenty of time to get there. Manager was arrogant and slow - didn't care. Poor policies at that airport.

1 / 10
American Airlines
PriceFrom $140
Free Cancellation
Rating
7.2
7.4

Boarding

7.1

Comfort

7.9

Crew

7.1

Entertainment

6.8

Food

Reviews

Pros: Nothing

Cons: Not charging me 100 dollars For a luggage that was 56 pounds

1 / 10
Alaska Airlines
PriceFrom $140
Free Cancellation
Rating
8.2
8.7

Boarding

8.3

Comfort

8.7

Crew

8.0

Entertainment

7.4

Food

Reviews

Pros: The flight wasn't full which is always nice and they served full size cans which is also a nice little note.

Cons: The plane was pretty old and people just started sitting wherever. It was chaos as my wife and I sat in our assigned seating and just watched people wander like animals.

1 / 10
United Airlines
PriceFrom $140
Free Cancellation
Rating
6.8
7.2

Boarding

6.6

Comfort

7.5

Crew

6.6

Entertainment

6.1

Food

Reviews

Cons: Sarasota ticketing agent was not very nice at all 😟 Houston Gate agent was not nice either. We were treated like we were stupid for asking questions. I hope it’s not racism issues. I wished I had taken their names.

1 / 10
Sun Country Air
PriceFrom $141
Free Cancellation
Rating
8.0
8.6

Boarding

7.6

Comfort

8.6

Crew

7.4

Entertainment

7.5

Food

Reviews

Pros: Quick boarding. Inexpensive ticket. Direct flight.

Cons: Crew walked thru cabin at least 5 times collecting garbage, but could not hand out sealed snack or sealed water. People sat should-to-shoulder - No buffer space, but asked to leave the plane with 6 foot intervals???? This airline picks and chooses their Covid precautions. Quick and inexpensive flight, if you don’t mind the rest.

1 / 3
Southwest
PriceFrom $374
Free Cancellation
Rating
8.4
8.6

Boarding

8.5

Comfort

8.8

Crew

7.6

Entertainment

7.8

Food

Reviews

Pros: The plane was new and the seats were nice.

1 / 10

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

Airlines such as Alaska Airlines 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.


Alternative routes for Portland to Chicago

Compare alternative flights to and from nearby airports and cities to discover the best prices and most convenient flight times
Eugene to Chicago Flights
Fastest flight time
9h 07m
Cheapest price
$261
Medford to Chicago Flights
Fastest flight time
9h 29m
Cheapest price
$261

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