Cheap flights from Chicago to Portland

Round-trip
Economy
Chicago (CHI)
Portland (PDX)
Fri 6/4
Fri 6/11
Any month
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Flight information for Chicago to Portland
(CHI to PDX)

Find info about flight duration, direct flights, and airports for your flight from Chicago to Portland
Best Price Found$197The best flight deal from Chicago to Portland found on momondo in the last 72 hours is $197
Fastest flight time4h 20mThe fastest flight from Chicago to Portland takes 4h 20m
Direct flightsMo, Tu, Sa and SuDirect flights go from Chicago to Portland on Monday, Tuesday, Saturday and Sunday. Airlines offering direct flights are: Southwest, Aer Lingus and Alaska Airlines.
Airports in Portland1 airportThere is 1 airport near Portland: Portland (PDX)

How to get the cheapest flight ticket from Chicago to Portland

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 Chicago to Portland?

August
The cheapest time of year to fly to Portland from Chicago is August. Most expensive is December

What is the cheapest day to depart Chicago for Portland?

Wednesday
The cheapest day of the week is typically Wednesday. The most expensive is typically Sunday

When is the cheapest time to fly from Chicago to Portland?

at noon
Chicago to Portland flights are approximately 28% more expensive in the evening than at noon

What is the cheapest airline that flies to Portland from Chicago?

Frontier
Frontier, Sun Country Air, and Spirit Airlines are the most popular carriers operating from Chicago to Portland

What is the cheapest Chicago to Portland flight route?

Chicago O'Hare Intl - Portland
Fly from Chicago O'Hare Intl to Portland for the best Chicago - Portland flight prices

How far in advance should you book Chicago to Portland flights?

29 days before
The cheapest time to buy a flight from Chicago to Portland is approximately 29 days to departure
60
Days before departure
0

Easily compare round-trip flights from Chicago to Portland

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 Chicago to Portland by changing tabs
United Airlines
Jun 5
ORD4:05 pmChicago O'Hare Intl
4h 22m
PDX8:27 pmPortland
Jun 9
PDX3:00 amPortland
3h 53m
ORD6:53 amChicago O'Hare Intl
Multiple Airlines
May 18
ORD4:30 amChicago O'Hare Intl
7h 57m
1 stop
PDX12:27 pmPortland
May 22
PDX10:40 amPortland
7h 03m
1 stop
ORD5:43 pmChicago O'Hare Intl
Multiple Airlines
May 10
ORD4:30 amChicago O'Hare Intl
12h 56m
1 stop
PDX5:26 pmPortland
May 26
PDX5:30 pmPortland
6h 30m
1 stop
ORD12:00 amChicago O'Hare Intl

Find the cheapest one-way flights from Chicago to Portland

If you're looking for one-way flights from Chicago to Portland, view some of our deals below provided by Frontier
Alaska Airlines
Jun 10
ORD3:55 pmChicago O'Hare Intl
4h 21m
PDX8:16 pmPortland
Alaska Airlines
May 25
ORD3:25 pmChicago O'Hare Intl
6h 05m
1 stop
PDX9:30 pmPortland
Frontier
May 11
ORD4:30 amChicago O'Hare Intl
7h 57m
1 stop
PDX12:27 pmPortland

Best airlines flying from Chicago to Portland

Compare and see reviews for airlines that fly from Chicago to Portland with momondo
AirlineRatingFree CancellationPrice
Frontier
PriceFrom $96
Free Cancellation
Rating
7.5
8.0

Boarding

7.1

Comfort

8.1

Crew

6.6

Entertainment

6.9

Food

Reviews

Cons: Everything is ok

1 / 10
Spirit Airlines
PriceFrom $116
Free Cancellation
Rating
7.1
7.5

Boarding

6.8

Comfort

7.7

Crew

6.3

Entertainment

6.4

Food

Reviews

Pros: Nothing

Cons: There’s no entertainment. Can’t even charge the phone. Can’t even recline the seat very uncomfortable flight

1 / 10
Sun Country Air
PriceFrom $131
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
Delta
PriceFrom $134
Free Cancellation
Rating
8.1
8.2

Boarding

8.4

Comfort

8.2

Crew

7.8

Entertainment

8.0

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

7.0

Entertainment

6.8

Food

Reviews

Pros: Yes made sure mask was in place

Cons: No

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

Boarding

8.5

Comfort

8.8

Crew

8.0

Entertainment

7.4

Food

Reviews

Pros: Accommodated to an earlier flight without questions asked.

Cons: Always been a delight!

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

Boarding

6.6

Comfort

7.5

Crew

6.6

Entertainment

6.0

Food

Reviews

Pros: everything

Cons: nono

1 / 10

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

Alaska Airlines and Delta have implemented additional safety measures to accommodate travelers. Airlines flying from Chicago to Portland are working to protect travelers. Some of these new policies include temperature checks, pre-flight testing, sanitization of key touchpoints, as well as mask requirements when onboard. Some airlines have even implemented socially distanced seating for a limited time. Policies will vary by airline.

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

Some of our partner airlines flying from Chicago to Portland are adopting new policies due to the global impact of COVID-19. Some of the airlines that may be waiving their cancellation fees are United Airlines, Alaska Airlines, and American Airlines. You can search for the full list of airlines like United Airlines that are offering this flexibility.


Alternative routes for Chicago to Portland

Compare alternative flights to and from nearby airports and cities to discover the best prices and most convenient flight times
Chicago to Eugene Flights
Fastest flight time
9h 34m
Cheapest price
$237
Chicago to Medford Flights
Fastest flight time
9h 08m
Cheapest price
$261

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