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Cheap flight deals from Portland to Chicago Starting at AED 208

Whether you’re going for a one-way or round-trip to Chicago, we’ve got you covered! Check out these different flight options from Portland below.

  • One way
  • Round-trip
      • Cheapest nonstop
        PWM06:00
        3h
        Nonstop
        ORD08:00
        Sun, Mar 30|Portland - Chicago|United Airlines
        AED 962AED 1,160
        17% OFF
        17% OFF
        AED 1,160AED 962

        Choose United Airlines flights from Portland to Chicago. The one-way direct flight with United Airlines departs from Portland International Jetport on Sun, Mar 30, arriving at O'Hare International Airport. One-way Prices start from AED 962 including taxes and charges.

      • PWM06:00
        3h 5m
        Nonstop
        ORD08:05
        Sun, Mar 16|Portland - Chicago|United Airlines
        AED 963AED 1,160
        17% OFF
        17% OFF
        AED 1,160AED 963

        Choose United Airlines flights from Portland to Chicago. The one-way direct flight with United Airlines departs from Portland International Jetport on Sun, Mar 16, arriving at O'Hare International Airport. One-way Prices start from AED 963 including taxes and charges.

      • PWM10:08
        9h 46m
        1 stop
        ORD18:54
        Thu, Mar 6|Portland - Chicago|Frontier Airlines
        AED 208AED 1,160
        82% OFF
        82% OFF
        AED 1,160AED 208

        Choose Frontier Airlines flights from Portland to Chicago. The one-way connecting flight with Frontier Airlines departs from Portland International Jetport on Thu, Mar 6, arriving at O'Hare International Airport. One-way Prices start from AED 208 including taxes and charges.

      • PWM20:35
        17h 45m
        1 stop
        ORD13:20
        Mon, Mar 3|Portland - Chicago|Frontier Airlines
        AED 222
        AED 222

        Choose Frontier Airlines flights from Portland to Chicago. The one-way connecting flight with Frontier Airlines departs from Portland International Jetport on Mon, Mar 3, arriving at O'Hare International Airport. One-way Prices start from AED 222 including taxes and charges.

      • PWM18:48
        21h 22m
        1 stop
        ORD15:10
        Wed, Mar 5|Portland - Chicago|Frontier Airlines
        AED 223
        AED 223

        Choose Frontier Airlines flights from Portland to Chicago. The one-way connecting flight with Frontier Airlines departs from Portland International Jetport on Wed, Mar 5, arriving at O'Hare International Airport. One-way Prices start from AED 223 including taxes and charges.

      • PWM20:35
        17h 45m
        1 stop
        ORD13:20
        Mon, Feb 24|Portland - Chicago|Frontier Airlines
        AED 235
        AED 235

        Choose Frontier Airlines flights from Portland to Chicago. The one-way connecting flight with Frontier Airlines departs from Portland International Jetport on Mon, Feb 24, arriving at O'Hare International Airport. One-way Prices start from AED 235 including taxes and charges.

      • PWM20:35
        26h 50m
        1 stop
        ORD22:25
        Fri, Feb 21|Portland - Chicago|Frontier Airlines
        AED 274
        AED 274

        Choose Frontier Airlines flights from Portland to Chicago. The one-way connecting flight with Frontier Airlines departs from Portland International Jetport on Fri, Feb 21, arriving at O'Hare International Airport. One-way Prices start from AED 274 including taxes and charges.

      • PWM10:23
        10h 16m
        1 stop
        ORD19:39
        Sat, Mar 1|Portland - Chicago|Frontier Airlines
        AED 290
        AED 290

        Choose Frontier Airlines flights from Portland to Chicago. The one-way connecting flight with Frontier Airlines departs from Portland International Jetport on Sat, Mar 1, arriving at O'Hare International Airport. One-way Prices start from AED 290 including taxes and charges.

      • PWM20:35
        15h 22m
        1 stop
        ORD10:57
        Mon, Mar 17|Portland - Chicago|Frontier Airlines
        AED 295
        AED 295

        Choose Frontier Airlines flights from Portland to Chicago. The one-way connecting flight with Frontier Airlines departs from Portland International Jetport on Mon, Mar 17, arriving at O'Hare International Airport. One-way Prices start from AED 295 including taxes and charges.

      • PWM10:08
        24h 19m
        1 stop
        ORD09:27
        Tue, Mar 4|Portland - Chicago|Frontier Airlines
        AED 296
        AED 296

        Choose Frontier Airlines flights from Portland to Chicago. The one-way connecting flight with Frontier Airlines departs from Portland International Jetport on Tue, Mar 4, arriving at O'Hare International Airport. One-way Prices start from AED 296 including taxes and charges.

      • PWM01:00 pm
        3h 5m
        Nonstop
        CHI02:00 pm
        Thu, Feb 20|Portland - Chicago|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.

Portland to Chicago flight time & flight schedules

Flight info.
Departure
Arrival
Weekly Schedule

  1. DL1017

    Delta Air Lines

    06:00

    PWM

    3.0h

    09:02

    ATL

    SMTWTFS
    Search

  2. DL2417

    Delta Air Lines

    11:00

    ATL

    1.9h

    11:56

    MDW

    SMTWT--

  3. F92621

    Frontier Airlines

    10:08

    PWM

    3.6h

    13:47

    MCO

    -M-W-FS
    Search

  4. F91457

    Frontier Airlines

    08:00

    MCO

    2.9h

    09:55

    MDW

    SMTWTFS

  5. F92621

    Frontier Airlines

    10:08

    PWM

    3.6h

    13:47

    MCO

    -M-W-FS
    Search

  6. F92041

    Frontier Airlines

    07:05

    MCO

    3.4h

    09:27

    ORD

    S-TWTFS

  7. F92621

    Frontier Airlines

    10:08

    PWM

    3.6h

    13:47

    MCO

    -M-W-FS
    Search

  8. F93043

    Frontier Airlines

    07:00

    MCO

    3.4h

    09:24

    ORD

    SMT-TF-

  9. DL5769

    Delta Air Lines

    11:40

    PWM

    1.5h

    13:08

    LGA

    SMTWTFS
    Search

  10. DL1078

    Delta Air Lines

    09:30

    LGA

    2.2h

    11:41

    DTW

    SMTWTF-

  11. DL3867

    Delta Air Lines

    12:15

    DTW

    1.3h

    12:30

    MDW

    SMTWTFS

  12. DL5399

    Delta Air Lines

    14:35

    PWM

    1.5h

    16:07

    JFK

    SMTWTFS
    Search

  13. DL3709

    Delta Air Lines

    18:55

    JFK

    3.0h

    20:54

    ORD

    SMTWTFS

  14. DL5295

    Delta Air Lines

    16:46

    PWM

    2.3h

    19:04

    DTW

    SMTWTFS
    Search

  15. DL1665

    Delta Air Lines

    20:10

    DTW

    1.4h

    20:34

    ORD

    SMTWTFS

  16. DL5796

    Delta Air Lines

    17:25

    PWM

    1.5h

    18:56

    LGA

    SMTWT-S
    Search

  17. DL2806

    Delta Air Lines

    20:55

    LGA

    2.8h

    22:42

    ORD

    SMTWT-S

  18. UA3582

    United Airlines

    19:09

    PWM

    1.9h

    21:04

    IAD

    SMTWTFS
    Search

  19. UA1738

    United Airlines

    22:07

    IAD

    2.1h

    23:15

    ORD

    SMTWTFS
Find more flights and airlines

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

Price trend charts are a great way of tracking how much your flights cost in the lead up to departure and can help you choose when to book your tickets. See how prices to Chicago from Portland have changed and are set to move below.

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

Frequently Asked Questions

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

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

  • How much do flights from Portland (PWM) to Chicago (CHI) cost?

    According to Trip.com's data, the lowest price is around AED 1,136.

  • How long does it take to fly from Portland (PWM) to Chicago (CHI)?

    It takes about 9 hours 55 minutes to fly from Portland (PWM) to Chicago (CHI).

  • What is the transportation method from the main airport to downtown in Chicago?

    • The distance from O'Hare International Airport to downtown is about 25 km, by taxi about 40 minutes.
    • The distance from Midway International Airport to downtown is about 14 km, by taxi about 30 minutes.

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

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

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

    United Airlines operates 2 non-stop flights from Portland (PWM) to Chicago (CHI).

  • How many airports are there in Chicago (CHI)?

How to find a cheap flight from Portland to Chicago

Understanding the common pitfalls when booking your flight tickets can help you save massively when it comes time to fly. We’ve listed our six essential steps to keep in mind when you’re booking flight tickets to help you find the best price.
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

Flight Info | Portland to Chicago

Cheapest direct flight priceAED 196
Cheapest return ticket priceAED 939
Off-season for travelDecember
Peak season for travelNovember
Flight distance1,425.81 km
Average flight time9 hours 55 minutes
Popular airlineDelta Air Lines

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