Airfare Deals Chicago to Portland

On HolidayPrice.com you will find 4 direct and 2 connecting flights from Chicago to Portland at a price of from $53. 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 CHI - PDX flight schedule to find best flight time, convenient departure and arrival airports.

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The cost of airline tickets from Chicago to Portland (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 Portland.

One way flight from Chicago to Portland

Below are the prices of tickets for direct one-way flights from Chicago to Portland. The cheapest flight from Chicago to Portland starts from $53 – the departure date for this flight is 14 February 2025.

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

Round trip from Chicago to Portland

You can buy a round-trip ticket from Chicago to Portland (United States) and back using the table below. The best offer starts from $130, the flight dates are: there on 13 February 2025 year and back on 15 February 2025 year.

Sort by: Departure dateCheap flightsTrip timeDirect flights
Alaska Airlines AS 325 Evening flight
Departure 15.11.25 20:05, Sa
Direct Trip 1 day
Return 17.11.25 07:00, Mo
*Prices include: baggage, hand luggage, airline fees and charges.
Not found promotions and sales.

Flight Schedule Chicago to Portland 2025

The current flight schedule for the route from Chicago to Portland 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 5 flights every day, from 4hours 30min. Local departure and arrival times are indicated.
07:0009:38
Alaska Airlines AS325 Alaska Airlines AS325
ORD → PDX
- Tu - Th Fr - -
Check price
09:0711:50
United Airlines UA2672 United Airlines UA2672
ORD → PDX
- - - Th Fr - -
Check price
09:1011:52
United Airlines UA2736 United Airlines UA2736
ORD → PDX
Mo Tu We Th Fr Sa -
Check price
09:1111:53
United Airlines UA2736 United Airlines UA2736
ORD → PDX
- - - - - - Su
Check price
11:0513:35
Southwest Airlines WN269 Southwest Airlines WN269
MDW → PDX
- - - - - Sa -
Check price
12:2019:25
Southwest Airlines WN590 Southwest Airlines WN590
MDW → PDX
- - - Th Fr - Su
Check price
13:5816:29
Alaska Airlines AS413 Alaska Airlines AS413
ORD → PDX
Mo Tu We - Fr Sa Su
Check price
14:0116:39
Alaska Airlines AS413 Alaska Airlines AS413
ORD → PDX
Mo - - Th Fr - -
Check price
16:0018:41
United Airlines UA2726 United Airlines UA2726
ORD → PDX
Mo Tu We Th Fr Sa Su
Check price
16:0518:49
United Airlines UA1616 United Airlines UA1616
ORD → PDX
Mo Tu - Th Fr Sa Su
Check price
16:2023:26
United Airlines UA2409 United Airlines UA2409
ORD → PDX
Mo - - Th Fr - -
Check price
18:5021:20
Southwest Airlines WN1675 Southwest Airlines WN1675
MDW → PDX
Mo - - Th Fr - Su
Check price
Show all

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

Flight Information

Flying to Portland from Chicago takes 04:17 minutes (excluding transfers). The distance between Chicago and Portland is 1746 miles (2811 kilometers). Planes depart from Chicago between 00:00 and 23:55. The fastest flight from the company Southwest Airlines with flight number WN 478. Flies for just 04:10 minutes with departure from Chicago Midway and arrival in Portland International Jetport.

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

04:10

Airlines

Direct flight

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

*Flight number

Flights with Transfers

Flights with transfers from Chicago to Portland can be bought from 2 airlines:

  • United Airlines: San Francisco, Long Beach, Seattle
  • American Airlines: Long Beach

*Transit cities

Airports

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

Chicago airports:

O'Hare  ~ 25 km* from $ 62Chicago Midway  ~ 14 km* from $ 95

Portland airports:

Portland International Jetport  ~ 4070 km* from $ 71

*Distance from the airport to the city center

Aircraft

You can fly from Chicago to Portland on board of 4 airlines that utilize 8 aircraft models.

  • Airbus A319
  • Airbus A320
  • Boeing 737
  • Boeing 737-700
  • Boeing 737-800
  • Boeing 737-900
  • Boeing 757-300
  • Embraer EMB 175

Connecting cities

The list of cities on transfer flights to Portland from Chicago. The best options are to fly through: San Francisco, Long Beach, Seattle.

Cheap airline tickets from Chicago to United States

Here is a list of flights from Chicago 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.

Chicago - New York AA 2382 American Airlines Boeing 737-800
01:13 O'Hare
in a way 1 hours 47 min Direct
03:00 Newark Liberty
Flights
from $27
13 February 2025
Chicago - Los Angeles AA 2744 American Airlines Airbus A321
20:03 O'Hare
in a way 3 hours 57 min Direct
00:00 Los Angeles
Flights
from $40
13 February 2025
Chicago - Miami WN 1909 Southwest Airlines Boeing 737-700
13:40 Chicago Midway
in a way 2 hours 55 min Direct
16:35 Fort Lauderdale Executive Airport
Flights
from $30
13 February 2025
Chicago - San Francisco AA 1312 American Airlines Boeing 737-800
17:55 O'Hare
in a way 4 hours 5 min Direct
22:00 Norman Y. Mineta San Jose
Flights
from $53
18 February 2025
Chicago - Boston UA 1420 United Airlines Airbus A320
17:05 O'Hare
in a way 1 hours 55 min Direct
19:00 Boston RT128 Railway
Flights
from $34
13 February 2025

All flights from Chicago

Flights from United States to Portland

Here are the cheapest flight bookings from United States to Portland 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 - Portland UA 2415 United Airlines Boeing 737-800
16:45 Newark Liberty
in a way 5 hours 46 min Direct
22:31 Portland International Jetport
Flights
from $90
18 February 2025
Los Angeles - Portland DL 69 Delta Air Lines Boeing 717-200
16:00 Los Angeles
in a way 2 hours 0 min Direct
18:00 Portland International Jetport
Flights
from $56
12 February 2025
Miami - Portland WN 5371 Southwest Airlines Boeing 737-700
00:05 Fort Lauderdale Executive Airport
in a way 8 hours 0 min Direct
08:05 Portland International Jetport
Flights
from $69
18 February 2025
Chicago - Portland WN 478 Southwest Airlines Boeing 737-800
03:25 Chicago Midway
in a way 4 hours 10 min Direct
07:35 Portland International Jetport
Flights
from $53
14 February 2025
San Francisco - Portland UA 1178 United Airlines Boeing 737-800
18:34 San Francisco
in a way 1 hours 26 min Direct
20:00 Portland International Jetport
Flights
from $22
18 February 2025

All flights to Portland

Tips for buying a ticket

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

Cheap flights from Chicago to Portland
Portland city

To start searching for tickets, Specify dates.

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