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Cheap flights from Chicago to Portland from $101

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 10/18. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Chicago to Portland

Cheap round-trip flights

Hawaiian Airlines Logo
2:04 pm - 4:37 pmORD-PDX
4h 33mnonstop
Hawaiian Airlines Logo
11:00 pm - 5:01 amPDX-ORD
4h 01mnonstop
$202Hawaiian Airlines
Find Deal
Sat, Oct 25 - Fri, Oct 31
Frontier Logo
9:47 pm - 11:56 amORD-PDX
16h 09m2 stops
Frontier Logo
3:26 pm - 12:15 amPDX-ORD
6h 49m1 stop
$203Frontier
Find Deal
Fri, Nov 7 - Mon, Nov 10
American Airlines Logo
7:09 am - 9:31 amORD-PDX
4h 22mnonstop
American Airlines Logo
11:58 pm - 5:53 amPDX-ORD
3h 55mnonstop
$205American Airlines
Find Deal
Thu, Oct 16 - Tue, Oct 21
Southwest Logo
8:45 am - 3:20 pmMDW-PDX
8h 35m1 stop
Southwest Logo
5:30 am - 7:45 pmPDX-MDW
12h 15m2 stops
$205Southwest
Find Deal
Wed, Nov 12 - Sun, Nov 16
Alaska Airlines Logo
2:05 pm - 4:39 pmORD-PDX
4h 34mnonstop
Alaska Airlines Logo
7:00 am - 1:04 pmPDX-ORD
4h 04mnonstop
$209Alaska Airlines
Find Deal
Wed, Feb 18 - Tue, Feb 24
Southwest Logo
6:25 pm - 12:15 amMDW-PDX
7h 50m2 stops
Southwest Logo
5:30 am - 7:45 pmPDX-MDW
12h 15m2 stops
$210Southwest
Find Deal
Thu, Nov 13 - Sun, Nov 16
United Airlines Logo
5:01 am - 9:29 amORD-PDX
6h 28m1 stop
United Airlines Logo
11:59 pm - 6:00 amPDX-ORD
4h 01mnonstop
$213United Airlines
Find Deal
Wed, Oct 15 - Sat, Oct 18
Alaska Airlines Logo
7:00 am - 9:32 amORD-PDX
4h 32mnonstop
Alaska Airlines Logo
11:00 pm - 5:01 amPDX-ORD
4h 01mnonstop
$215Alaska Airlines
Find Deal
Sat, Oct 11 - Wed, Oct 15
American Airlines Logo
7:09 am - 9:31 amORD-PDX
4h 22mnonstop
American Airlines Logo
11:58 pm - 5:53 amPDX-ORD
3h 55mnonstop
$222American Airlines
Find Deal
Fri, Oct 24 - Fri, Oct 31
United Airlines Logo
1:10 pm - 3:30 pmORD-PDX
4h 20mnonstop
United Airlines Logo
2:15 pm - 8:25 pmPDX-ORD
4h 10mnonstop
$231United Airlines
Find Deal
Tue, Oct 14 - Tue, Oct 21

Hawaiian Airlines flights from Chicago to Portland

Our best Hawaiian Airlines deals on Chicago to Portland flight tickets
Hawaiian Airlines
Oct 25
ORD2:04 pmChicago O'Hare Intl
4h 33m
PDX4:37 pmPortland
Oct 31
PDX11:00 pmPortland
4h 01m
ORD5:01 amChicago O'Hare Intl
$202
Find similar
Hawaiian Airlines
Oct 25
ORD6:00 amChicago O'Hare Intl
8h 25m
1 stop
PDX12:25 pmPortland
Oct 31
PDX11:00 pmPortland
4h 01m
ORD5:01 amChicago O'Hare Intl
$208
Find similar
Hawaiian Airlines
Feb 18
ORD2:05 pmChicago O'Hare Intl
4h 34m
PDX4:39 pmPortland
Feb 24
PDX4:00 pmPortland
5h 59m
1 stop
ORD11:59 pmChicago O'Hare Intl
$219
Find similar

American Airlines flights from Chicago to Portland

Our best American Airlines deals on Chicago to Portland flight tickets
American Airlines
Oct 16
ORD7:09 amChicago O'Hare Intl
4h 22m
PDX9:31 amPortland
Oct 21
PDX11:58 pmPortland
3h 55m
ORD5:53 amChicago O'Hare Intl
$205
Find similar
American Airlines
Oct 24
ORD7:09 amChicago O'Hare Intl
4h 22m
PDX9:31 amPortland
Oct 31
PDX11:58 pmPortland
3h 55m
ORD5:53 amChicago O'Hare Intl
$222
Find similar

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 September 17, 2025.
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

Sat 10/25

2:04 pm-4:37 pm

Nonstop4h 33m

Portland

Fri 10/31

11:00 pm-5:01 am

Nonstop4h 01m

$202

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Fri 11/7

9:47 pm-11:56 am

2 stops16h 09m

Portland

Mon 11/10

3:26 pm-12:15 am

1 stop6h 49m

$203

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Thu 10/16

7:09 am-9:31 am

Nonstop4h 22m

Portland

Tue 10/21

11:58 pm-5:53 am

Nonstop3h 55m

$205

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Wed 11/12

8:45 am-3:20 pm

1 stop8h 35m

Portland

Sun 11/16

5:30 am-7:45 pm

2 stops12h 15m

$205

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Wed 2/18

2:05 pm-4:39 pm

Nonstop4h 34m

Portland

Tue 2/24

7:00 am-1:04 pm

Nonstop4h 04m

$209

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Thu 11/13

6:25 pm-12:15 am

2 stops7h 50m

Portland

Sun 11/16

5:30 am-7:45 pm

2 stops12h 15m

$210

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Wed 10/15

5:01 am-9:29 am

1 stop6h 28m

Portland

Sat 10/18

11:59 pm-6:00 am

Nonstop4h 01m

$213

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Sat 10/11

7:00 am-9:32 am

Nonstop4h 32m

Portland

Wed 10/15

11:00 pm-5:01 am

Nonstop4h 01m

$215

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Fri 10/24

7:09 am-9:31 am

Nonstop4h 22m

Portland

Fri 10/31

11:58 pm-5:53 am

Nonstop3h 55m

$222

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Tue 10/14

1:10 pm-3:30 pm

Nonstop4h 20m

Portland

Tue 10/21

2:15 pm-8:25 pm

Nonstop4h 10m

$231

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 January. Flight prices, which tend to average around $274, are often lower during this time because this is during the off-season. If you don’t want to visit Portland in January, then you should wait until September to fly from Chicago, when ticket prices are also cheap, with an average price of $278.

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 $330. 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 $406.

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 $326. At noon is when there is more demand to fly to Portland, so prices are often more expensive at around $449 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 $334 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 $287 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 September 2025, prices for Chicago to Portland flights are approximately 13% cheaper 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

$89

Fastest flight time

4h 15m

Direct flights

Every day

Airports in Portland

1 airport
The best one-way flight to Portland from Chicago in the past 72 hours is $89. The best round-trip flight deal from Chicago to Portland found on momondo in the last 72 hours is $249.
The fastest flight from Chicago to Portland takes 4h 15m
Direct flights go from Chicago to Portland every day.
There is 1 airport near Portland: 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
8,023 reviews
Search Spirit Airlines flights
FrontierPriceFrom $108Free CancellationRating
5.8
3,173 reviews
Search Frontier flights
DeltaPriceFrom $123Free CancellationRating
7.9
7,961 reviews
Search Delta flights
Hawaiian AirlinesPriceFrom $134Free CancellationRating
7.8
2,729 reviews
Search Hawaiian Airlines flights
Alaska AirlinesPriceFrom $183Free CancellationRating
8.0
10,000 reviews
Search Alaska Airlines flights
American AirlinesPriceFrom $213Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $227Free CancellationRating
7.4
8,926 reviews
Search United Airlines flights
SouthwestPriceFrom $238Free CancellationRating
8.0
4,242 reviews
Search Southwest flights

  • Alaska Airlines Flights From Chicago to Portland

    Alaska Airlines flight deals from Chicago to Portland start from $183 round-trip. Over the 7 Alaska Airlines flights for this route in a normal week, average airfare is usually $289 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, 4,242 ratings). Southwest flies from Chicago to Portland around 15 times per week, with deals starting from $238 round-trip and rising to an average price of around $453.

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
Gresham
McMinnville
Longview
Tigard
The Dalles
Pacific City
Tillamook
Manzanita

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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