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Portland International Jetport to Chicago flight
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Cheap Flights from Portland International Jetport to Chicago

Search for flights from Portland International Jetport to Chicago and check out affordable one-way and round-trip options.

  • One way
  • Round-trip
sortSort: Price (Lowest)
  • Sort: Price (Lowest)
  • Sort: Departure (Earliest)
      • PWM12:59
        12h 28m
        1 stop
        ORD00:27
        Portland - Chicago|Sun, Nov 10|Frontier Airlines
        CAD 93CAD 211
        56% OFF
        56% OFF
        CAD 211CAD 93
      • PWM13:14
        11h 50m
        1 stop
        ORD00:04
        Portland - Chicago|Sun, Sep 29|Frontier Airlines
        CAD 99CAD 211
        53% OFF
        53% OFF
        CAD 211CAD 99
      • PWM13:14
        11h 50m
        1 stop
        ORD00:04
        Portland - Chicago|Sun, Oct 6|Frontier Airlines
        CAD 100CAD 211
        53% OFF
        53% OFF
        CAD 211CAD 100
      • PWM13:22
        11h 45m
        1 stop
        ORD00:07
        Portland - Chicago|Sun, Oct 27|Frontier Airlines
        CAD 100
        CAD 100
      • PWM09:52
        13h 3m
        1 stop
        MDW21:55
        Portland - Chicago|Mon, Oct 14|Frontier Airlines
        CAD 114
        CAD 114
      • PWM18:02
        24h 41m
        1 stop
        ORD17:43
        Portland - Chicago|Fri, Nov 1|Frontier Airlines
        CAD 119
        CAD 119
      • PWM18:02
        24h 41m
        1 stop
        ORD17:43
        Portland - Chicago|Fri, Oct 25|Frontier Airlines
        CAD 120
        CAD 120
      • PWM17:54
        24h 47m
        1 stop
        ORD17:41
        Portland - Chicago|Fri, Nov 8|Frontier Airlines
        CAD 120
        CAD 120
      • PWM06:15
        2h 46m
        Direct
        ORD08:01
        Portland - Chicago|Wed, Sep 25|United Airlines
        CAD 129
        CAD 129
      • PWM08:10
        14h 42m
        1 stop
        ORD21:52
        Portland - Chicago|Thu, Oct 3|Jetblue Airways
        CAD 151
        CAD 151
      • PWM13:00
        3h 5m
        Direct
        CHI14:00
        Portland - Chicago|Wed, Oct 2|Frontier Airlines
        Find More Flights
        Find More Flights

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

Selected Airlines from Portland International Jetport to Chicago

See which airlines fly from Portland International Jetport to Chicago. Find the airline that best meets your travel needs by comparing prices and treat yourself to an enjoyable journey.

Frontier Airlines
From CAD 93
United Airlines
From CAD 129
Jetblue Airways
From CAD 151
American Airlines
From CAD 154
Delta Air Lines
From CAD 167
Sun Country Airlines
From CAD 240
Southwest Airlines
From CAD 554

Find more flights and airlines

Find Suitable Airport in Chicago

Learn about different airports in Chicago, find the best flight and transfer options, and plan your journey.

  • 24.74 km from central ChicagoCheapest
    O'Hare International Airport
    Tickets From
    CAD 93
  • 12.76 km from central ChicagoClosest
    Midway International Airport
    Tickets From
    CAD 114
Flight Schedule from Portland International Jetport to Chicago

Check the schedule for flights from Portland International Jetport to Chicago and find the flight that best matches your travel plans.

Flight info.
Departure
Arrival
Weekly Schedule

  1. UA1778

    United Airlines

    06:00

    PWM

    3.0h

    Direct

    07:57

    ORD

    SM-WTFS
    Search

  2. UA1328

    United Airlines

    06:00

    PWM

    2.8h

    Direct

    07:46

    ORD

    --T----
    Search

  3. AA2781

    American Airlines

    06:01

    PWM

    2.6h

    08:39

    CLT

    SMTWTFS
    Search

  4. AA2052

    American Airlines

    11:06

    CLT

    2.1h

    12:15

    ORD

    SMTWTFS

  5. AA1283

    American Airlines

    07:26

    PWM

    1.6h

    09:04

    PHL

    SMTWTFS
    Search

  6. AA1959

    American Airlines

    10:30

    PHL

    2.5h

    12:00

    ORD

    SMTWTFS

  7. AA3524

    American Airlines

    12:15

    PWM

    2.8h

    Direct

    14:04

    ORD

    SMTWTFS
    Search

  8. AA2282

    American Airlines

    14:27

    PWM

    2.6h

    17:02

    CLT

    SMTWTFS
    Search

  9. AA1048

    American Airlines

    20:50

    CLT

    2.1h

    21:58

    ORD

    SMTWTFS

  10. DL5702

    Delta Air Lines

    14:52

    PWM

    1.5h

    16:23

    JFK

    SMTWTFS
    Search

  11. DL3709

    Delta Air Lines

    18:55

    JFK

    3.1h

    21:00

    ORD

    SMTWTFS

  12. UA1612

    United Airlines

    16:49

    PWM

    2.8h

    Direct

    18:35

    ORD

    SM-WTFS
    Search

  13. UA3689

    United Airlines

    16:50

    PWM

    1.6h

    18:28

    EWR

    SM-WTFS
    Search

  14. NK329

    Spirit Airlines

    21:15

    EWR

    2.6h

    22:52

    ORD

    SMTWTFS

  15. AA3531

    American Airlines

    17:51

    PWM

    2.8h

    Direct

    19:40

    ORD

    S--WT-S
    Search
Find more flights and airlines

Flight Info of Flights from Portland International Jetport to Chicago

Cheapest return ticket price

CAD 298

Cheapest direct flight price

CAD 93

Off-season travel month

August

Peak season for travel

December

FAQs for Portland International Jetport to Chicago Flights

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