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Cheap flights from Chicago to Portland from $119

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Portland departing on 4/20. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Chicago to Portland

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
11:20 am - 1:53 pm
ORD
-
PDX
4h 33mnonstop
American Airlines Logo
2:43 pm - 9:02 pm
PDX
-
ORD
4h 19mnonstop
$214American Airlines
Wed, Feb 4 - Wed, Feb 11
Delta Logo
2:05 pm - 8:25 pm
MDW
-
PDX
8h 20m
1 stop
Delta Logo
12:30 am - 8:50 am
PDX
-
MDW
6h 20m
1 stop
$217Delta
Tue, Mar 10 - Tue, Mar 10
United Airlines Logo
8:15 pm - 10:56 pm
ORD
-
PDX
4h 41mnonstop
United Airlines Logo
3:50 pm - 11:59 pm
PDX
-
ORD
6h 09m
1 stop
$217United Airlines
Sat, Feb 14 - Wed, Feb 18
American Airlines Logo
9:46 pm - 12:17 am
ORD
-
PDX
4h 31mnonstop
American Airlines Logo
11:59 pm - 5:56 am
PDX
-
ORD
3h 57mnonstop
$218American Airlines
Fri, Mar 6 - Fri, Mar 13
Southwest Logo
1:55 pm - 10:30 pm
MDW
-
PDX
10h 35m
2 stops
Southwest Logo
5:20 am - 11:15 am
PDX
-
MDW
3h 55mnonstop
$219Southwest
Sat, Feb 28 - Sat, Mar 7
Southwest Logo
3:40 pm - 8:45 pm
MDW
-
PDX
7h 05m
1 stop
Southwest Logo
11:55 pm - 5:50 am
PDX
-
MDW
3h 55mnonstop
$223Southwest
Wed, Apr 29 - Fri, May 1
Alaska Airlines Logo
6:06 pm - 10:46 pm
ORD
-
PDX
6h 40m
1 stop
Alaska Airlines Logo
7:05 am - 1:10 pm
PDX
-
ORD
4h 05mnonstop
$224Alaska Airlines
Tue, Feb 3 - Tue, Feb 10
Hawaiian Airlines Logo
2:07 pm - 4:50 pm
ORD
-
PDX
4h 43mnonstop
Hawaiian Airlines Logo
8:30 am - 4:33 pm
PDX
-
ORD
6h 03m
1 stop
$226Hawaiian Airlines
Sat, Feb 14 - Sat, Feb 21
Alaska Airlines Logo
2:07 pm - 4:50 pm
ORD
-
PDX
4h 43mnonstop
Alaska Airlines Logo
3:52 pm - 11:56 pm
PDX
-
ORD
6h 04m
1 stop
$227Alaska Airlines
Fri, Mar 6 - Mon, Mar 9
Hawaiian Airlines Logo
2:07 pm - 4:50 pm
ORD
-
PDX
4h 43mnonstop
Hawaiian Airlines Logo
8:30 am - 4:33 pm
PDX
-
ORD
6h 03m
1 stop
$228Hawaiian Airlines
Sat, Feb 14 - Sat, Feb 21

Southwest flights from Chicago to Portland

Our best Southwest deals on Chicago to Portland flight tickets
Southwest
Feb 28
MDW1:55 pmChicago Midway
10h 35m
2 stops
PDX10:30 pmPortland
Mar 7
PDX5:20 amPortland
3h 55m
MDW11:15 amChicago Midway
$219
Southwest
Mar 21
MDW10:30 pmChicago Midway
4h 25m
PDX12:55 amPortland
Mar 24
PDX11:55 pmPortland
3h 50m
MDW5:45 amChicago Midway
$231
Southwest
Feb 18
MDW2:10 pmChicago Midway
10h 05m
1 stop
PDX10:15 pmPortland
Feb 23
PDX6:45 amPortland
3h 55m
MDW12:40 pmChicago Midway
$233

Alaska Airlines flights from Chicago to Portland

Our best Alaska Airlines deals on Chicago to Portland flight tickets
Alaska Airlines
Feb 3
ORD6:06 pmChicago O'Hare Intl
6h 40m
1 stop
PDX10:46 pmPortland
Feb 10
PDX7:05 amPortland
4h 05m
ORD1:10 pmChicago O'Hare Intl
$224
Alaska Airlines
Mar 25
ORD2:09 pmChicago O'Hare Intl
4h 41m
PDX4:50 pmPortland
Apr 8
PDX7:03 amPortland
4h 10m
ORD1:13 pmChicago O'Hare Intl
$231
Alaska Airlines
Mar 10
ORD2:07 pmChicago O'Hare Intl
4h 43m
PDX4:50 pmPortland
Mar 15
PDX7:00 amPortland
4h 11m
ORD1:11 pmChicago O'Hare Intl
$232

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to Portland that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated January 21, 2026.
Use the filters below to find and compare flights from Chicago to Portland that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Wed 2/4

11:20 am-1:53 pm

Nonstop4h 33m

Portland

Wed 2/11

2:43 pm-9:02 pm

Nonstop4h 19m

$214

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Tue 3/10

2:05 pm-8:25 pm

1 stop8h 20m

Portland

Tue 3/10

12:30 am-8:50 am

1 stop6h 20m

$217

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Sat 2/14

8:15 pm-10:56 pm

Nonstop4h 41m

Portland

Wed 2/18

3:50 pm-11:59 pm

1 stop6h 09m

$217

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Fri 3/6

9:46 pm-12:17 am

Nonstop4h 31m

Portland

Fri 3/13

11:59 pm-5:56 am

Nonstop3h 57m

$218

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Sat 2/28

1:55 pm-10:30 pm

2 stops10h 35m

Portland

Sat 3/7

5:20 am-11:15 am

Nonstop3h 55m

$219

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Wed 4/29

3:40 pm-8:45 pm

1 stop7h 05m

Portland

Fri 5/1

11:55 pm-5:50 am

Nonstop3h 55m

$223

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Tue 2/3

6:06 pm-10:46 pm

1 stop6h 40m

Portland

Tue 2/10

7:05 am-1:10 pm

Nonstop4h 05m

$224

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Sat 2/14

2:07 pm-4:50 pm

Nonstop4h 43m

Portland

Sat 2/21

8:30 am-4:33 pm

1 stop6h 03m

$226

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Fri 3/6

2:07 pm-4:50 pm

Nonstop4h 43m

Portland

Mon 3/9

3:52 pm-11:56 pm

1 stop6h 04m

$227

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Sat 2/14

2:07 pm-4:50 pm

Nonstop4h 43m

Portland

Sat 2/21

8:30 am-4:33 pm

1 stop6h 03m

$228

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Portland from

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

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

What is the cheapest month to fly to Portland?

The cheapest month to fly to Portland from Chicago is in September. Flight prices, which tend to average around $280, are often lower during this time because this is during the off-season. If you don’t want to visit Portland in September, then you should wait until May to fly from Chicago, when ticket prices are also cheap, with an average price of $283.

What is the cheapest day to depart on your flight to Portland?

The cheapest day to depart on your flight to Portland is on a Wednesday when prices can be found for as low as $332. This is often the case because there is less demand to fly during this day of the week. The most expensive day to fly to Portland is Monday, with ticket prices averaging around $394.

What is the cheapest time of day to depart on your flight to Portland?

The cheapest time of day to fly to Portland is in the evening when flights can be purchased for as low as $316. At noon is when there is more demand to fly to Portland, so prices are often more expensive at around $460 per ticket.

What is the cheapest Chicago to Portland flight route?

Fly from Chicago Midway to Portland for the best Chicago - Portland flight prices

How far in advance should I book a flight 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 $329 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Portland from Chicago for as low as $272 on momondo.

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

There are 4 cabin classes 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 January 2026, prices for Chicago to Portland flights are approximately 9% 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 round-trip 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

$138

Fastest flight time

4h 20m

Direct flights

Every day

Airports in Portland

1 airport
The best one-way flight to Portland from Chicago in the past 72 hours is $138. The best round-trip flight deal from Chicago to Portland found on momondo in the last 72 hours is $237.
The fastest flight from Chicago to Portland takes 4h 20m
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

  • How far is Chicago to Portland by plane?

    A flight from Chicago to Portland will travel around 1753.4 mi. Flights usually cover this in 4h 20m, depending on flying conditions and air traffic around both airports.

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

    Prices for flights from Chicago to Portland Airport refresh daily.

  • How many operators does momondo search for flights from Chicago to Portland Airport?

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

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for 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 license, 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?

  • What is the most popular airline from Chicago to Portland?

Best airlines flying from Chicago to Portland

Compare and see reviews for airlines that fly from Chicago to Portland with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $86Free CancellationRating
6.3
8,364 reviews
Search Spirit Airlines flights
Hawaiian AirlinesPriceFrom $128Free CancellationRating
7.8
2,829 reviews
Search Hawaiian Airlines flights
FrontierPriceFrom $150Free CancellationRating
5.7
3,057 reviews
Search Frontier flights
Alaska AirlinesPriceFrom $197Free CancellationRating
8.0
11,775 reviews
Search Alaska Airlines flights
United AirlinesPriceFrom $205Free CancellationRating
7.4
9,191 reviews
Search United Airlines flights
American AirlinesPriceFrom $211Free CancellationRating
7.2
11,173 reviews
Search American Airlines flights
SouthwestPriceFrom $247Free CancellationRating
8.0
4,266 reviews
Search Southwest flights

  • Alaska Airlines Flights From Chicago to Portland

    Alaska Airlines flight deals from Chicago to Portland start from $197 round-trip. Over the 5 Alaska Airlines flights for this route in a normal week, average airfare is usually $309 round-trip - but some users have found much cheaper deals with momondo.

  • Southwest Flights From Chicago to Portland

    Another popular option for Chicago to Portland flights is Southwest (8.0/10, 4,266 ratings). Southwest flies from Chicago to Portland around 7 times per week, with deals starting from $247 round-trip and rising to an average price of around $419.

Traveling to a place near Portland?

Book flights to Portland if you plan to visit one of these locations
Lincoln City
Seaside
Cannon Beach
Vancouver
Salem
Astoria
Long Beach
Depoe Bay
Rockaway Beach
Beaverton
Hillsboro
Hood River
McMinnville
Longview
Tigard
Gresham
Pacific City
The Dalles
Manzanita
Newberg

Why use momondo?

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

It is quick and easy to find Chicago to Portland flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Portland that suits you.

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

All flight searches from Chicago to Portland on momondo can be filtered to show those which offer flexible booking policies.

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

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Chicago to Portland.

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

Yes. momondo can track prices for Chicago to Portland flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

An easier way to manage your Portland trip

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