Airfare Deals Portland to Chicago

On HolidayPrice.com you will find 4 direct and 7 connecting flights from Portland to Chicago at a price of from $93. You can compare airfare deals from airlines and multiple travel sites, book and save on cheap plane tickets and last minute offers. Also check out PDX - CHI flight schedule to find best flight time, convenient departure and arrival airports.

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The cost of airline tickets from Portland to Chicago (United States) and back without transfers can be found with the help of the calendar. Specify the search parameters: one way or round-trip, payment currency, click on the month/day you need and we will search for flights to Chicago.

One way flight from Portland to Chicago

Below are the prices of tickets for direct one-way flights from Portland to Chicago. The cheapest flight from Portland to Chicago starts from $ 93 – the departure date for this flight is 14 September 2021.

Sort by: Departure dateCheap flightsFast flightsDirect flights
27.08.2021 Friday
from $ 187 Kiwi.com
Economy Found 2 days
1 Stopover 23 hours 32 min
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25.08.2021 Wednesday
from $ 214 FlyFar
Economy Found 2021-07-20
1 Stopover 18 hours 50 min
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28.08.2021 Saturday
from $ 237 City.Travel
Economy Found 2021-07-21
1 Stopover 38 hours 22 min
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14.08.2021 Saturday
from $ 242 JustFly
Economy Found 2021-07-21
1 Stopover 25 hours 34 min
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18.08.2021 Wednesday
from $ 266 FlyFar
Economy Found 2021-07-21
1 Stopover 12 hours 48 min
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13.08.2021 Friday
from $ 285 Kiwi.com
Economy Found 2021-07-21
1 Stopover 21 hours 57 min
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02.08.2021 Monday
from $ 289 Trip.com
Economy Found 2021-07-18
1 Stopover 18 hours 46 min
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19.08.2021 Thursday
from $ 296 FlightNetwork
Economy Found 2021-07-21
1 Stopover 12 hours 48 min
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13.08.2021 Friday
from $ 296 FlightNetwork
Economy Found 2021-07-21
1 Stopover 12 hours 47 min
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12.08.2021 Thursday
from $ 313 MyHolidays
Economy Found 2021-07-21
1 Stopover 13 hours 21 min
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19.08.2021 Thursday
from $ 319 Trip.com
Economy Found yesterday
1 Stopover 12 hours 36 min
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01.08.2021 Sunday
from $ 376 MyHolidays
Economy Found 2 days
1 Stopover 12 hours 31 min
Find Flights
*Prices include: baggage, hand luggage, airline fees and charges.

Round trip from Portland to Chicago

You can buy a round-trip ticket from Portland to Chicago (United States) and back using the table below. The best offer starts from $ 161, the flight dates are: there on 22 September 2021 year and back on 29 September 2021 year.

Sort by: Departure dateCheap flightsTrip timeDirect flights
Frontier Airlines F9 792 Morning flight
Departure 22.09.21 07:37, We
1 Stopover Trip 7 days
Return 29.09.21 13:00, We
Frontier Airlines F9 2178 Day flight
Departure 09.09.21 16:53, Th
1 Stopover Trip 5 days
Return 14.09.21 14:30, Tu
Spirit Airlines NK 1236 Night flight
Departure 28.08.21 03:05, Sa
1 Stopover Trip 16 days
Return 13.09.21 11:30, Mo
United Airlines UA 1490 Morning flight
Departure 11.09.21 06:40, Sa
1 Stopover Trip 3 days
Return 14.09.21 14:00, Tu
Frontier Airlines F9 2178 Day flight
Departure 23.09.21 16:53, Th
1 Stopover Trip 6 days
Return 29.09.21 14:30, We
Spirit Airlines NK 1236 Night flight
Departure 26.08.21 03:05, Th
1 Stopover Trip 20 days
Return 15.09.21 14:00, We
Frontier Airlines F9 792 Morning flight
Departure 28.08.21 07:37, Sa
1 Stopover Trip 17 days
Return 14.09.21 01:02, Tu
Frontier Airlines F9 792 Morning flight
Departure 14.08.21 07:37, Sa
1 Stopover Trip 5 days
Return 19.08.21 00:55, Th
Spirit Airlines NK 1236 Night flight
Departure 19.08.21 03:05, Th
1 Stopover Trip 3 days
Return 22.08.21 00:55, Su
Delta Air Lines DL 2725 Evening flight
Departure 02.09.21 20:36, Th
1 Stopover Trip 3 days
Return 05.09.21 13:00, Su
Spirit Airlines NK 1236 Night flight
Departure 14.08.21 03:05, Sa
1 Stopover Trip 4 days
Return 18.08.21 02:30, We
Spirit Airlines NK 1236 Night flight
Departure 03.08.21 03:05, Tu
1 Stopover Trip 4 days
Return 07.08.21 13:50, Sa
Spirit Airlines NK 1236 Night flight
Departure 20.08.21 03:05, Fr
1 Stopover Trip 2 days
Return 22.08.21 00:55, Su
American Airlines AA 1853 Morning flight
Departure 26.07.21 06:50, Mo
1 Stopover Trip 6 days
Return 01.08.21 13:50, Su
United Airlines UA 2177 Evening flight
Departure 04.03.22 22:15, Fr
Direct Trip 19 days
Return 23.03.22 17:55, We
Southwest Airlines WN 1759 Day flight
Departure 12.08.21 12:55, Th
1 Stopover Trip 4 days
Return 16.08.21 12:15, Mo
United Airlines UA 1490 Morning flight
Departure 24.07.21 06:55, Sa
1 Stopover Trip 1 day
Return 25.07.21 13:50, Su
American Airlines AA 1853 Morning flight
Departure 25.07.21 06:50, Su
1 Stopover Trip 7 days
Return 01.08.21 13:50, Su
Frontier Airlines F9 2172 Night flight
Departure 02.08.21 01:40, Mo
1 Stopover Trip 2 days
Return 04.08.21 12:15, We
Frontier Airlines F9 792 Morning flight
Departure 26.07.21 07:35, Mo
1 Stopover Trip 5 days
Return 31.07.21 17:59, Sa
Spirit Airlines NK 1236 Night flight
Departure 31.07.21 03:05, Sa
2 Stopovers Trip 3 days
Return 02.08.21 15:49, Mo
*Prices include: baggage, hand luggage, airline fees and charges.

Flight Schedule Portland to Chicago 2021

The current flight schedule for the route from Portland to Chicago for today, tomorrow and the next few days. This schedule will help you decide on the time of departure and arrival, the airline, the flight number and the day of the week.

More than 10 flights every day, from 3hours 44min. Local departure and arrival times are indicated.
05:3011:25
Southwest Airlines WN237 Southwest Airlines WN237
PDX → MDW
- - - - - Sa -
Check price
06:0520:00
Southwest Airlines WN623 Southwest Airlines WN623
PDX → MDW
- Tu We - - - -
Check price
06:2516:20
Southwest Airlines WN4376 Southwest Airlines WN4376
PDX → MDW
- Tu We - - - -
Check price
06:3512:30
Southwest Airlines WN1537 Southwest Airlines WN1537
PDX → MDW
Mo - - Th Fr - -
Check price
06:4012:35
Southwest Airlines WN3427 Southwest Airlines WN3427
PDX → MDW
- - - - - - Su
Check price
06:4512:40
Southwest Airlines WN4870 Southwest Airlines WN4870
PDX → MDW
- Tu We - - - -
Check price
07:1018:40
Southwest Airlines WN4117 Southwest Airlines WN4117
PDX → MDW
- - - - - Sa -
Check price
07:1113:00
United Airlines UA1693 United Airlines UA1693
PDX → ORD
Mo Tu We Th Fr Sa Su
Check price
08:3017:30
Southwest Airlines WN29 Southwest Airlines WN29
PDX → ORD
- - - - - - Su
Check price
10:1018:40
Southwest Airlines WN3072 Southwest Airlines WN3072
PDX → MDW
- - - - - - Su
Check price
11:0517:00
Southwest Airlines WN459 Southwest Airlines WN459
PDX → MDW
- Tu We - - - -
Check price
11:0716:59
United Airlines UA2334 United Airlines UA2334
PDX → ORD
Mo Tu We Th Fr Sa Su
Check price
Show all

*Schedule is indicated only for direct scheduled flights and low-cost airlines.

Flight Information

Flying to Chicago from Portland takes 04:17 minutes (excluding transfers). The distance between Portland and Chicago is 1746 miles (2811 kilometers). Planes depart from Portland between 00:00 and 23:55. The fastest flight from the company American Airlines with flight number AA 1442. Flies for just 03:41 minutes with departure from Portland International Jetport and arrival in O'Hare.

time

Average flight time

04:17 min

distance

Distance

1746 mi

The earliest flight

The earliest flight

00:00

The latest flight

The latest flight

23:55

Airplane

The fastest flight

03:41

Airlines

Direct flight

There are 4 airlines that fly directly from Portland to Chicago. The most popular company carrying out non-stop flights is United Airlines.

*Flight number

Flights with Transfers

Flights with transfers from Portland to Chicago can be bought from 7 airlines:

  • American Airlines: Long Beach
  • Frontier Airlines: Las Vegas, Denver
  • Alaska Airlines: Dallas, Spokane, San Diego
  • Sun Country Airlines: Saint Paul Island
  • United Airlines: Denver
  • Southwest Airlines: Las Vegas, Denver
  • Delta Air Lines: Long Beach, Seattle

*Transit cities

Airports

Airports serving the air communication between Portland and Chicago. You can fly to Chicago from 1 Portland airports. Planes arrive at 2 airport in Chicago.

Portland airports:

Portland International Jetport  ~ 4070 km* from $ 78

Chicago airports:

O'Hare  ~ 25 km* from $ 80Chicago Midway  ~ 14 km* from $ 120

*Distance from the airport to the city center

Aircraft

You can fly from Portland to Chicago on board of 4 airlines that utilize 7 aircraft models.

  • Airbus A319
  • Airbus A320
  • Boeing 737
  • Boeing 737-700
  • Boeing 737-800
  • Boeing 737-900
  • Embraer EMB 175

Connecting cities

The list of cities on transfer flights to Chicago from Portland. The best options are to fly through: Long Beach, Las Vegas, Dallas, Spokane, San Diego, Saint Paul Island, Denver, Salt Lake City, San Francisco, Seattle, Phoenix.

Cheap airline tickets from Portland to United States

Here is a list of flights from Portland to United States purchased on HolidayPrice.com in the past 48 hours. If you find an interesting offer for cheap tickets, do not delay your purchase, prices change every 15 minutes.

Portland - New York UA 2417 United Airlines Airbus A320
09:22 Portland International Jetport
in a way 4 hours 38 min Direct
14:00 Newark Liberty
Flights
from $ 106
28 September 2021
Portland - Los Angeles DL 473 Delta Air Lines Airbus A319
22:00 Portland International Jetport
in a way 2 hours 0 min Direct
00:00 Los Angeles
Flights
from $ 75
15 September 2021
Portland - Miami WN 4963 Southwest Airlines Boeing 737-800
15:45 Portland International Jetport
in a way 9 hours 35 min Direct
01:20 Fort Lauderdale Executive Airport
Flights
from $ 98
31 August 2021
Portland - Chicago AA 1442 American Airlines Boeing 737-800
23:19 Portland International Jetport
in a way 3 hours 41 min Direct
03:00 O'Hare
Flights
from $ 93
14 September 2021
Portland - San Francisco UA 2233 United Airlines Boeing 737-800
04:40 Portland International Jetport
in a way 1 hours 20 min Direct
06:00 San Francisco
Flights
from $ 75
12 August 2021

All flights from Portland

Flights from United States to Chicago

Here are the cheapest flight bookings from United States to Chicago made by users of our website. If you didn’t find your flight destination, use the search bar at the top of the page.

New York - Chicago UA 761 United Airlines Boeing 737-800
13:00 LaGuardia
in a way 2 hours 0 min Direct
15:00 O'Hare
Flights
from $ 51
25 August 2021
Los Angeles - Chicago UA 910 United Airlines Boeing 737-800
10:23 Los Angeles
in a way 3 hours 37 min Direct
14:00 O'Hare
Flights
from $ 64
24 August 2021
Miami - Chicago AA 2796 American Airlines Boeing 767-300
17:05 Miami
in a way 2 hours 55 min Direct
20:00 O'Hare
Flights
from $ 24
01 September 2021
San Francisco - Chicago UA 1800 United Airlines Airbus A319
04:15 San Francisco
in a way 3 hours 45 min Direct
08:00 O'Hare
Flights
from $ 86
14 September 2021
Boston - Chicago UA 789 United Airlines Boeing 737-900
02:44 Boston RT128 Railway
in a way 2 hours 16 min Direct
05:00 O'Hare
Flights
from $ 50
28 August 2021

All flights to Chicago

Tips for buying a ticket

Portland – Chicago – Portland round-trip route are always cheaper than tickets purchased there and back separately.

Cheap flights from Portland to Chicago
Chicago city

To start searching for tickets, Specify dates.

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