Flights from Portland to Chicago from $58

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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 $58. 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.

Sun

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.

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Cheap flights from Portland
Cheap flights to Chicago
Airline tickets to United States

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 $58 – the departure date for this flight is 21 May 2025.

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07.06.2025 Saturday

from $84 Gotogate

Economy Found today

1 Stopover 13 hours 48 min

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*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 $175, the flight dates are: there on 21 May 2025 year and back on 23 May 2025 year.

*Prices include: baggage, hand luggage, airline fees and charges.

Not found promotions and sales.

Flight Schedule Portland to Chicago 2025

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 9 flights every day, from 3hours 57min. Local departure and arrival times are indicated.

05:30 → 11:30

Southwest Airlines WN407

PDX → MDW

Mo - - Th Fr - -

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06:00 → 12:00

Southwest Airlines WN407

PDX → MDW

- - - - - - Su

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06:15 → 12:15

Southwest Airlines WN407

PDX → MDW

- Tu We - - - -

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06:45 → 12:45

Southwest Airlines WN407

PDX → MDW

- - - - - Sa -

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07:00 → 13:05

Alaska Airlines AS327

PDX → ORD

Mo Tu We Th Fr Sa Su

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07:00 → 13:03

United Airlines UA1693

PDX → ORD

Mo Tu We Th Fr Sa Su

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07:00 → 12:57

United Airlines UA1693

PDX → ORD

- - - - - Sa -

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10:50 → 16:56

United Airlines UA534

PDX → ORD

Mo Tu We Th Fr - Su

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10:50 → 16:53

United Airlines UA534

PDX → ORD

- - - - - Sa -

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13:25 → 19:32

American Airlines AA2515

PDX → ORD

- Tu - - - Sa -

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14:02 → 20:08

United Airlines UA2360

PDX → ORD

Mo Tu We Th Fr Sa Su

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14:25 → 00:15

United Airlines UA321

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.

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.

United Airlines: UA 1444, UA 294, UA 789
Southwest Airlines: WN 2097, WN 5240, WN 5441
American Airlines: AA 2298, AA 1442
Alaska Airlines: AS 686, AS 1070, AS 692

*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.

Long Beach
Las Vegas
Dallas
Spokane
San Diego

Saint Paul Island
Denver
Salt Lake City
San Francisco
Seattle

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 $140 22 May 2025

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 $39 21 May 2025

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 $73 26 May 2025

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 $58 21 May 2025

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 $25 26 May 2025

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 $33 20 May 2025

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 $48 20 May 2025

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 $36 22 May 2025

Miami - Chicago WN 1626 Southwest Airlines Boeing 737

13:35 Fort Lauderdale Executive Airport

in a way 3 hours 0 min Direct

16:35 Chicago Midway

Flights
from $36 22 May 2025

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 $83 20 May 2025

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

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