How many flights depart from Chicago to Portland on average per week?

As of November 2026, 103 flights take off from Chicago and land in Portland each week. The most common flight departure day for this route is Sun, with 20% of weekly flights taking off on this day.

What is the cheapest airline that flies from Chicago to Portland?

Delta and United Airlines are the most popular carriers operating from Chicago to Portland

How many flights depart from Chicago to Portland on average per day?

The number of flights available between Chicago and Portland is 14 per day as of November 2026. The most frequent departure time is 17:00, with 63% of daily flights leaving in the afternoon.

When did momondo last update prices for flights from Chicago to Portland Airport?

Prices for flights from Chicago to Portland Airport are updated daily.

How old do you have to be to fly from Chicago to Portland Airport?

The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago to Portland Airport.

What documentation or ID do you need to fly to Portland Airport?

The travel and health documents required for your trip to Portland Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s licence, and a passport valid for six-months after you plan to arrive at Portland Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

R3 026 Cheap Flights from Chicago to Portland in 2026/27

Find the cheapest flights from Chicago to Portland

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One-way

Last minute

Direct

Cheap return flights

Enter your travel dates to find the best prices.

7:27 - 13:38ORD Chicago O'Hare Intl-PDX Portland

8h 11m1 stop San Diego

7:00 - 13:10PDX Portland-ORD Chicago O'Hare Intl

4h 10mdirect

R5 871Alaska Airlines

Wed, Dec 9 - Sat, Dec 12

12:38 - 18:55ORD Chicago O'Hare Intl-PDX Portland

8h 17m2 stops Minneapolis St Paul Seattle/Tacoma Intl

9:23 - 21:56PDX Portland-ORD Chicago O'Hare Intl

10h 33m2 stops Seattle/Tacoma Intl Salt Lake City

R5 903Delta

Thu, Nov 26 - Thu, Dec 10

14:08 - 17:05ORD Chicago O'Hare Intl-PDX Portland

4h 57mdirect

19:18 - 5:37PDX Portland-ORD Chicago O'Hare Intl

8h 19m1 stop Seattle/Tacoma Intl

R5 936Alaska Airlines

Fri, Dec 4 - Fri, Dec 4

14:13 - 20:50ORD Chicago O'Hare Intl-PDX Portland

8h 37m1 stop San Diego

8:30 - 19:10PDX Portland-ORD Chicago O'Hare Intl

8h 40m1 stop Seattle/Tacoma Intl

R5 953Alaska Airlines

Tue, Dec 1 - Sat, Dec 5

14:08 - 17:05ORD Chicago O'Hare Intl-PDX Portland

4h 57mdirect

7:00 - 13:10PDX Portland-ORD Chicago O'Hare Intl

4h 10mdirect

R5 969Alaska Airlines

Sat, Dec 5 - Sat, Dec 12

7:15 - 17:08ORD Chicago O'Hare Intl-PDX Portland

11h 53m2 stops Salt Lake City Seattle/Tacoma Intl

14:10 - 23:27PDX Portland-ORD Chicago O'Hare Intl

7h 17m1 stop Los Angeles

R5 986Delta

Wed, Jan 6 - Sun, Jan 10

16:30 - 22:45ORD Chicago O'Hare Intl-PDX Portland

8h 15m1 stop San Francisco

14:26 - 20:28PDX Portland-ORD Chicago O'Hare Intl

4h 02mdirect

R6 002United Airlines

Tue, Dec 1 - Sat, Dec 5

18:14 - 0:47ORD Chicago O'Hare Intl-PDX Portland

8h 33m1 stop San Francisco

23:50 - 5:59PDX Portland-ORD Chicago O'Hare Intl

4h 09mdirect

R6 019United Airlines

Sat, Dec 19 - Tue, Dec 29

14:08 - 17:05ORD Chicago O'Hare Intl-PDX Portland

4h 57mdirect

7:00 - 13:10PDX Portland-ORD Chicago O'Hare Intl

4h 10mdirect

R6 035Alaska Airlines

Wed, Dec 9 - Fri, Dec 11

6:20 - 10:48ORD Chicago O'Hare Intl-PDX Portland

6h 28m1 stop Minneapolis St Paul

5:30 - 18:06PDX Portland-ORD Chicago O'Hare Intl

10h 36m2 stops Seattle/Tacoma Intl Salt Lake City

R6 068Delta

Mon, Dec 7 - Sun, Dec 13

Cheap last-minute flights

Enter your travel dates to find the best prices.

16:25 - 19:12ORD Chicago O'Hare Intl-PDX Portland

4h 47mdirect

14:26 - 20:28PDX Portland-ORD Chicago O'Hare Intl

4h 02mdirect

R7 433United Airlines

Fri, Nov 13 - Tue, Dec 15

16:25 - 19:12ORD Chicago O'Hare Intl-PDX Portland

4h 47mdirect

19:25 - 5:25PDX Portland-ORD Chicago O'Hare Intl

8h 00m1 stop San Francisco

R7 597United Airlines

Fri, Nov 13 - Tue, Dec 15

17:55 - 23:36ORD Chicago O'Hare Intl-PDX Portland

7h 41m1 stop Seattle/Tacoma Intl

7:00 - 16:50PDX Portland-ORD Chicago O'Hare Intl

7h 50m1 stop Seattle/Tacoma Intl

R7 762Delta

Fri, Nov 13 - Tue, Dec 15

17:05 - 19:47ORD Chicago O'Hare Intl-PDX Portland

4h 42mdirect

23:09 - 5:07PDX Portland-ORD Chicago O'Hare Intl

3h 58mdirect

R8 617American Airlines

Wed, Nov 11 - Mon, Nov 16

19:45 - 22:27ORD Chicago O'Hare Intl-PDX Portland

4h 42mdirect

7:00 - 13:07PDX Portland-ORD Chicago O'Hare Intl

4h 07mdirect

R8 666United Airlines

Tue, Nov 10 - Wed, Nov 11

9:59 - 17:48ORD Chicago O'Hare Intl-PDX Portland

9h 49m1 stop Dallas/Fort Worth

23:09 - 5:07PDX Portland-ORD Chicago O'Hare Intl

3h 58mdirect

R8 781American Airlines

Wed, Nov 11 - Mon, Nov 16

14:07 - 16:50ORD Chicago O'Hare Intl-PDX Portland

4h 43mdirect

17:45 - 5:40PDX Portland-ORD Chicago O'Hare Intl

9h 55m1 stop Seattle/Tacoma Intl

R8 831Alaska Airlines

Tue, Nov 10 - Sat, Nov 14

8:40 - 13:22ORD Chicago O'Hare Intl-PDX Portland

6h 42m1 stop Denver Intl

19:26 - 5:00PDX Portland-ORD Chicago O'Hare Intl

7h 34m1 stop San Francisco

R8 913United Airlines

Wed, Nov 11 - Wed, Nov 11

5:00 - 11:06ORD Chicago O'Hare Intl-PDX Portland

8h 06m1 stop Dallas/Fort Worth

5:14 - 14:43PDX Portland-ORD Chicago O'Hare Intl

7h 29m1 stop Phoenix Sky Harbor Intl

R8 946American Airlines

Wed, Nov 11 - Mon, Nov 16

19:17 - 23:51ORD Chicago O'Hare Intl-PDX Portland

6h 34m1 stop Salt Lake City

6:45 - 17:05PDX Portland-ORD Chicago O'Hare Intl

8h 20m1 stop Atlanta Hartsfield-Jackson

R8 995Delta

Tue, Nov 10 - Sat, Nov 14

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Delta flights from Chicago to Portland

Our best Delta deals on Chicago to Portland flight tickets

Delta

Nov 26

ORD12:38Chicago O'Hare Intl

8h 17m

2 stops

PDX18:55Portland

Dec 10

PDX9:23Portland

10h 33m

2 stops

ORD21:56Chicago O'Hare Intl

R5 903

Delta

Jan 6

ORD7:15Chicago O'Hare Intl

11h 53m

2 stops

PDX17:08Portland

Jan 10

PDX14:10Portland

7h 17m

1 stop

ORD23:27Chicago O'Hare Intl

R5 986

Delta

Dec 9

ORD19:18Chicago O'Hare Intl

6h 41m

1 stop

PDX23:59Portland

Dec 12

PDX5:30Portland

9h 20m

1 stop

ORD16:50Chicago O'Hare Intl

R6 035

Alaska Airlines flights from Chicago to Portland

Our best Alaska Airlines deals on Chicago to Portland flight tickets

Alaska Airlines

Dec 9

ORD7:27Chicago O'Hare Intl

8h 11m

1 stop

PDX13:38Portland

Dec 12

PDX7:00Portland

4h 10m

ORD13:10Chicago O'Hare Intl

R5 871

Alaska Airlines

Dec 4

ORD14:08Chicago O'Hare Intl

4h 57m

PDX17:05Portland

Dec 4

PDX19:18Portland

8h 19m

1 stop

ORD5:37Chicago O'Hare Intl

R5 936

Alaska Airlines

Dec 1

ORD14:13Chicago O'Hare Intl

8h 37m

1 stop

PDX20:50Portland

Dec 5

PDX8:30Portland

8h 40m

1 stop

ORD19:10Chicago O'Hare Intl

R5 953

Fly from

Fly to

Route

Depart

Return

Price

Cheapest return flight

ChicagoPortland

ORD Chicago O'Hare Intl - PDX Portland

ORDPDX

Chicago O'Hare Intl

Wed 9/12

7:27-13:38

1 stop8h 11m

Portland

Sat 12/12

7:00-13:10

Nonstop4h 10m

R5 871

ChicagoPortland

ORD Chicago O'Hare Intl - PDX Portland

ORDPDX

Chicago O'Hare Intl

Thu 26/11

12:38-18:55

2 stops8h 17m

Portland

Thu 10/12

9:23-21:56

2 stops10h 33m

R5 903

ChicagoPortland

ORD Chicago O'Hare Intl - PDX Portland

ORDPDX

Chicago O'Hare Intl

Fri 4/12

14:08-17:05

Nonstop4h 57m

Portland

Fri 4/12

19:18-5:37

1 stop8h 19m

R5 936

ChicagoPortland

ORD Chicago O'Hare Intl - PDX Portland

ORDPDX

Chicago O'Hare Intl

Tue 1/12

14:13-20:50

1 stop8h 37m

Portland

Sat 5/12

8:30-19:10

1 stop8h 40m

R5 953

Fastest return journey

ChicagoPortland

ORD Chicago O'Hare Intl - PDX Portland

ORDPDX

Chicago O'Hare Intl

Sat 5/12

14:08-17:05

Nonstop4h 57m

Portland

Sat 12/12

7:00-13:10

Nonstop4h 10m

R5 969

ChicagoPortland

ORD Chicago O'Hare Intl - PDX Portland

ORDPDX

Chicago O'Hare Intl

Wed 6/1

7:15-17:08

2 stops11h 53m

Portland

Sun 10/1

14:10-23:27

1 stop7h 17m

R5 986

ChicagoPortland

ORD Chicago O'Hare Intl - PDX Portland

ORDPDX

Chicago O'Hare Intl

Tue 1/12

16:30-22:45

1 stop8h 15m

Portland

Sat 5/12

14:26-20:28

Nonstop4h 02m

R6 002

ChicagoPortland

ORD Chicago O'Hare Intl - PDX Portland

ORDPDX

Chicago O'Hare Intl

Sat 19/12

18:14-0:47

1 stop8h 33m

Portland

Tue 29/12

23:50-5:59

Nonstop4h 09m

R6 019

ChicagoPortland

ORD Chicago O'Hare Intl - PDX Portland

ORDPDX

Chicago O'Hare Intl

Wed 9/12

14:08-17:05

Nonstop4h 57m

Portland

Fri 11/12

7:00-13:10

Nonstop4h 10m

R6 035

ChicagoPortland

ORD Chicago O'Hare Intl - PDX Portland

ORDPDX

Chicago O'Hare Intl

Mon 7/12

6:20-10:48

1 stop6h 28m

Portland

Sun 13/12

5:30-18:06

2 stops10h 36m

R6 068

Flights are sorted by cheapest return flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Chicago to Portland

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Other information

What is the typical price of a round-trip flight between Chicago and Portland?

Prices are currently low for flights on this route.

Typical prices usually range from R6 167 to R9 620.
The lowest price recently found on this route was R5 871.

What is the cheapest month to fly to Portland?

In general, February is the cheapest month to fly from Chicago to Portland. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around R4 867. If you are unable to visit Portland during the month of February, then departing from Chicago during the month January is also very affordable. Most momondo users find prices during this month for around R5 114.

What is the cheapest Chicago to Portland flight route?

Fly from Chicago O'Hare Intl to Portland for the best Chicago - Portland flight prices

How far in advance should I book a flight from Chicago to Portland?

You are more likely to see cheaper flights to Portland from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Portland for around R6 186 when searching weeks before you fly. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Portland from Chicago for as low as R4 407 on momondo.

What cabin class options are available on Chicago to Portland flights?

There is only 1 cabin class available to choose from on Chicago to Portland flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

How have Chicago to Portland flight prices changed over time?

As of November 2026, prices for Chicago to Portland flights are approximately 74% more expensive when compared to flights at the same time last year.

When to book flights from Chicago to Portland

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago to Portland according to our flight data. Find out which month and days have the cheapest flights.

Estimated return price

Cheap Chicago to Portland (CHI to PDX) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Portland

Best price found	R3 026
Direct flights	Every day
Airports in Portland	1 airport

The best one-way flight to Portland from Chicago in the past 72 hours is R3 026. The best return flight deal from Chicago to Portland found on momondo in the last 72 hours is R5 871.

Direct flights go from Chicago to Portland every day.

There is 1 airport in Portland. From Chicago there are direct flights to Portland (PDX).

Search flight deals

Frequently asked questions about flying from Chicago to Portland

How far is Chicago to Portland by plane?
The distance between Chicago and Portland is about 2821,8 km.
When did momondo last update prices for flights from Chicago to Portland Airport?
Prices for flights from Chicago to Portland Airport are updated daily.
How old do you have to be to fly from Chicago to Portland Airport?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago to Portland Airport.
What documentation or ID do you need to fly to Portland Airport?
The travel and health documents required for your trip to Portland Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s licence, and a passport valid for six-months after you plan to arrive at Portland Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Chicago to Portland?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Chicago to Portland is Boeing 737-800 (27,18% of total bookings). The next most popular plane models are Boeing 737 MAX 8 (16,43%), Airbus A321-100/200 (15,31%), and Airbus A321neo (13,62%).

Astoria

Beaverton

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Portland?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Chicago to Portland for you.

Can I find flights from Chicago to Portland with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Portland from Chicago with this policy.

How can momondo help me find flights from Chicago to Portland?

momondo helps you find the best flight between Chicago and Portland by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Chicago to Portland right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Chicago to Portland now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Portland and let you know when they change.