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Cheap Flights from Chicago to Portland
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Cheap Flights from Chicago to Portland starting at TWD 1,789

Discover our range of affordable one-way and round-trip flights from Chicago to Portland and kick-start your next adventure today!

  • One way
  • Round-trip
      • Cheapest nonstop
        ORD11:10
        2h 32m
        Nonstop
        PWM14:42
        Thu, Feb 6|Chicago - Portland|United Airlines
        TWD 6,739TWD 10,831
        38% OFF
        38% OFF
        TWD 10,831TWD 6,739

        Fly from Chicago to Portland on Thu, Feb 6 with United Airlines. One-way direct flights with United Airlines depart O'Hare International Airport and arrive Portland International Jetport starting at TWD 6,739 including taxes and charges.

      • ORD18:00
        2h 22m
        Nonstop
        PWM21:22
        Sun, Mar 16|Chicago - Portland|United Airlines
        TWD 9,639TWD 10,831
        11% OFF
        11% OFF
        TWD 10,831TWD 9,639

        Fly from Chicago to Portland on Sun, Mar 16 with United Airlines. One-way direct flights with United Airlines depart O'Hare International Airport and arrive Portland International Jetport starting at TWD 9,639 including taxes and charges.

      • ORD07:25
        9h 13m
        1 stop
        PWM17:38
        Wed, Feb 26|Chicago - Portland|Frontier Airlines
        TWD 1,789TWD 10,831
        83% OFF
        83% OFF
        TWD 10,831TWD 1,789

        Fly from Chicago to Portland on Wed, Feb 26 with Frontier Airlines. One-way connecting flights with Frontier Airlines depart O'Hare International Airport and arrive Portland International Jetport starting at TWD 1,789 including taxes and charges.

      • ORD05:05
        12h 29m
        1 stop
        PWM18:34
        Mon, Mar 10|Chicago - Portland|Frontier Airlines
        TWD 1,933
        TWD 1,933

        Fly from Chicago to Portland on Mon, Mar 10 with Frontier Airlines. One-way connecting flights with Frontier Airlines depart O'Hare International Airport and arrive Portland International Jetport starting at TWD 1,933 including taxes and charges.

      • ORD20:44
        11h 34m
        1 stop
        PWM09:18
        Sat, Feb 15|Chicago - Portland|Frontier Airlines
        TWD 1,983
        TWD 1,983

        Fly from Chicago to Portland on Sat, Feb 15 with Frontier Airlines. One-way connecting flights with Frontier Airlines depart O'Hare International Airport and arrive Portland International Jetport starting at TWD 1,983 including taxes and charges.

      • MDW11:33
        7h 39m
        1 stop
        PWM20:12
        Mon, Feb 10|Chicago - Portland|Frontier Airlines
        TWD 2,186
        TWD 2,186

        Fly from Chicago to Portland on Mon, Feb 10 with Frontier Airlines. One-way connecting flights with Frontier Airlines depart Midway International Airport and arrive Portland International Jetport starting at TWD 2,186 including taxes and charges.

      • ORD16:18
        26h 54m
        1 stop
        PWM20:12
        Sun, Feb 9|Chicago - Portland|Frontier Airlines
        TWD 2,322
        TWD 2,322

        Fly from Chicago to Portland on Sun, Feb 9 with Frontier Airlines. One-way connecting flights with Frontier Airlines depart O'Hare International Airport and arrive Portland International Jetport starting at TWD 2,322 including taxes and charges.

      • ORD07:25
        9h 13m
        1 stop
        PWM17:38
        Wed, Feb 19|Chicago - Portland|Frontier Airlines
        TWD 2,408
        TWD 2,408

        Fly from Chicago to Portland on Wed, Feb 19 with Frontier Airlines. One-way connecting flights with Frontier Airlines depart O'Hare International Airport and arrive Portland International Jetport starting at TWD 2,408 including taxes and charges.

      • ORD07:25
        9h 13m
        1 stop
        PWM17:38
        Wed, Mar 5|Chicago - Portland|Frontier Airlines
        TWD 2,624
        TWD 2,624

        Fly from Chicago to Portland on Wed, Mar 5 with Frontier Airlines. One-way connecting flights with Frontier Airlines depart O'Hare International Airport and arrive Portland International Jetport starting at TWD 2,624 including taxes and charges.

      • MDW12:43
        19h 35m
        1 stop
        PWM09:18
        Mon, Feb 17|Chicago - Portland|Frontier Airlines
        TWD 3,415
        TWD 3,415

        Fly from Chicago to Portland on Mon, Feb 17 with Frontier Airlines. One-way connecting flights with Frontier Airlines depart Midway International Airport and arrive Portland International Jetport starting at TWD 3,415 including taxes and charges.

      • CHI01:00 pm
        3h 5m
        Nonstop
        PWM02:00 pm
        Thu, Feb 13|Chicago - Portland|United Airlines
        Find More Flights
        Find More Flights

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

Chicago to Portland Flight Time

Flight info.
Departure
Arrival
Weekly Schedule

  1. UA2343

    United Airlines

    06:00

    ORD

    2.2h

    09:11

    EWR

    SMTWTFS
    Search

  2. UA3716

    United Airlines

    09:29

    EWR

    1.3h

    10:48

    PWM

    SMTWTFS

  3. DL3863

    Delta Air Lines

    07:20

    ORD

    2.3h

    10:39

    JFK

    SMTWTFS
    Search

  4. DL5399

    Delta Air Lines

    12:59

    JFK

    1.4h

    14:22

    PWM

    SMTWTFS

  5. DL3858

    Delta Air Lines

    09:20

    MDW

    1.2h

    11:32

    DTW

    SMTWTFS
    Search

  6. DL4094

    Delta Air Lines

    14:10

    DTW

    1.9h

    16:03

    PWM

    ----TFS

  7. DL3858

    Delta Air Lines

    09:20

    MDW

    1.2h

    11:32

    DTW

    SMTWTFS
    Search

  8. DL5295

    Delta Air Lines

    14:10

    DTW

    1.9h

    16:03

    PWM

    SMT----

  9. DL1520

    Delta Air Lines

    09:30

    ORD

    1.2h

    11:44

    DTW

    SMTWT-S
    Search

  10. DL5295

    Delta Air Lines

    14:10

    DTW

    1.9h

    16:03

    PWM

    SMT----

  11. DL1083

    Delta Air Lines

    10:10

    ORD

    1.5h

    12:42

    DTW

    -----F-
    Search

  12. DL4094

    Delta Air Lines

    14:10

    DTW

    1.9h

    16:03

    PWM

    ----TFS

  13. F91458

    Frontier Airlines

    12:49

    MDW

    2.8h

    16:37

    MCO

    S--WTFS
    Search

  14. F92622

    Frontier Airlines

    17:25

    MCO

    3.3h

    20:43

    PWM

    S--WT-S

  15. DL2307

    Delta Air Lines

    16:59

    MDW

    1.9h

    19:55

    ATL

    ----TFS
    Search

  16. DL2138

    Delta Air Lines

    21:28

    ATL

    2.5h

    23:59

    PWM

    SMTWTFS

  17. DL5609

    Delta Air Lines

    17:10

    ORD

    2.3h

    20:30

    LGA

    SMTWT-S
    Search

  18. DL5818

    Delta Air Lines

    21:50

    LGA

    1.3h

    23:10

    PWM

    SMTWT-S

  19. DL976

    Delta Air Lines

    17:13

    ORD

    2.1h

    20:20

    ATL

    SMTWTFS
    Search

  20. DL2138

    Delta Air Lines

    21:28

    ATL

    2.5h

    23:59

    PWM

    SMTWTFS
Find more flights and airlines

Cheapest time to fly from Chicago to Portland

Explore the best time to buy affordable tickets to Portland with our price trend chart, which predicts how flight prices will change in the coming weeks from previous data.

Displayed prices are calculated based on the lowest average weekly prices of the corresponding route on Trip.com.

Frequently Asked Questions

  • When to buy flight tickets from Chicago (CHI) to Portland (PWM) the cheapest?

    Airlines adjust prices for flights from Chicago to Portland based on the date and time of your booking. By analyzing data from all airlines, on Trip.com, you can find the cheapest flight prices on Tuesdays, Wednesdays, and Saturdays.

  • How much is a flight from Chicago (CHI) to Portland (PWM) cost?

    According to Trip.com's data, the lowest price is around TWD 10,664.

  • How long is a flight from Chicago (CHI) to Portland (PWM)?

    It takes about 2 hours 30 minutes to fly from Chicago (CHI) to Portland (PWM).

  • What are the most popular airlines that fly from Chicago (CHI) to Portland (PWM)?

    Airlines with flights from Chicago (CHI) to Portland (PWM): United Airlines and Air New Zealand.

  • What's the most popular airline for direct flights from Chicago (CHI) to Portland (PWM)?

    United Airlines operates 5 direct flights from Chicago (CHI) to Portland (PWM).

  • How many airports in Portland?

    There are 1 airports near Portland: Portland International Jetport.

How to find a cheap flight from Chicago to Portland

If you don’t know some of the key things to look out for when buying flight tickets, prices can often end up sky high or, worse, sold out! We’ve carefully compiled our six most important steps to help ensure you’re getting the best deals when planning your next journey.
1
Book Early
Once prices are gone, they're gone. Lock in deals while you can!
2
Compare Flight Prices
Compare prices on travel agency and airline websites.
3
Look Out for Deals
Check airline and travel agency websites for latest flight deals
4
Check One-way Fares
Buying two cheap one-way flights can sometimes be a better deal than a round-trip.
5
Try Different Dates
Flying during the week, early in the morning, or late at night can help save money.
6
Use the Trip.com App
Save up to £10 per person when booking your flights on Trip.com

Find cheapest flight ticket from Chicago to Portland

Cheapest direct flight priceTWD 1,788
Cheapest return ticket priceTWD 8,419
Off-season for travelFebruary
Peak season for travelApril
Flight distance1,425.81km
Average flight time2 hours 30 minutes
Popular airlineDelta Air Lines

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