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Cheap flights from Chicago to Portland from $111

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 11/1. 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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Cheap round-trip flights

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Multiple Airlines Logo
6:45 pm - 1:08 pmORD-PDX
20h 23m1 stop
Multiple Airlines Logo
5:15 pm - 7:43 amPDX-ORD
36h 28m2 stops
$207Multiple Airlines
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Thu, Nov 20 - Mon, Dec 1
Delta Logo
8:50 am - 12:54 pmORD-PDX
6h 04m1 stop
Delta Logo
12:32 am - 8:40 amPDX-ORD
6h 08m1 stop
$208Delta
Find Deal
Thu, Dec 4 - Sat, Dec 6
Southwest Logo
9:50 pm - 12:20 amMDW-PDX
4h 30mnonstop
Southwest Logo
2:15 pm - 10:55 pmPDX-MDW
6h 40m1 stop
$209Southwest
Find Deal
Fri, Nov 14 - Tue, Nov 18
American Airlines Logo
5:58 pm - 8:31 pmORD-PDX
4h 33mnonstop
American Airlines Logo
6:00 am - 12:15 pmPDX-ORD
4h 15mnonstop
$215American Airlines
Find Deal
Sun, Jan 11 - Sun, Feb 1
Alaska Airlines Logo
2:05 pm - 4:48 pmORD-PDX
4h 43mnonstop
Alaska Airlines Logo
7:44 pm - 6:21 amPDX-ORD
8h 37m1 stop
$216Alaska Airlines
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Sat, Dec 6 - Sat, Dec 13
Southwest Logo
1:55 pm - 10:35 pmMDW-PDX
10h 40m1 stop
Southwest Logo
5:35 am - 5:00 pmPDX-MDW
9h 25m2 stops
$216Southwest
Find Deal
Tue, Jan 13 - Thu, Jan 15
American Airlines Logo
8:14 am - 10:48 amORD-PDX
4h 34mnonstop
American Airlines Logo
1:26 pm - 7:41 pmPDX-ORD
4h 15mnonstop
$217American Airlines
Find Deal
Wed, Nov 12 - Sat, Nov 15
Alaska Airlines Logo
2:05 pm - 4:48 pmORD-PDX
4h 43mnonstop
Alaska Airlines Logo
2:37 pm - 6:21 amPDX-ORD
13h 44m1 stop
$226Alaska Airlines
Find Deal
Fri, Dec 5 - Sun, Dec 7
United Airlines Logo
4:10 pm - 6:45 pmORD-PDX
4h 35mnonstop
United Airlines Logo
11:59 pm - 5:52 amPDX-ORD
3h 53mnonstop
$232United Airlines
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Sat, Dec 6 - Sat, Dec 13
United Airlines Logo
4:15 pm - 6:56 pmORD-PDX
4h 41mnonstop
United Airlines Logo
11:59 pm - 6:00 amPDX-ORD
4h 01mnonstop
$241United Airlines
Find Deal
Mon, Jan 26 - Wed, Jan 28

Delta flights from Chicago to Portland

Our best Delta deals on Chicago to Portland flight tickets
Delta
Dec 4
ORD8:50 amChicago O'Hare Intl
6h 04m
1 stop
PDX12:54 pmPortland
Dec 6
PDX12:32 amPortland
6h 08m
1 stop
ORD8:40 amChicago O'Hare Intl
$208
Find similar
Delta
Dec 11
ORD6:10 pmChicago O'Hare Intl
6h 30m
1 stop
PDX10:40 pmPortland
Dec 15
PDX7:30 pmPortland
11h 10m
2 stops
ORD8:40 amChicago O'Hare Intl
$211
Find similar
Delta
Nov 14
MDW1:47 pmChicago Midway
9h 00m
1 stop
PDX8:47 pmPortland
Nov 18
PDX11:15 pmPortland
7h 39m
1 stop
MDW8:54 amChicago Midway
$219
Find similar

Southwest flights from Chicago to Portland

Our best Southwest deals on Chicago to Portland flight tickets
Southwest
Nov 14
MDW9:50 pmChicago Midway
4h 30m
PDX12:20 amPortland
Nov 18
PDX2:15 pmPortland
6h 40m
1 stop
MDW10:55 pmChicago Midway
$209
Find similar
Southwest
Jan 13
MDW1:55 pmChicago Midway
10h 40m
1 stop
PDX10:35 pmPortland
Jan 15
PDX5:35 amPortland
9h 25m
2 stops
MDW5:00 pmChicago Midway
$216
Find similar
Southwest
Dec 16
MDW5:15 amChicago Midway
8h 10m
1 stop
PDX11:25 amPortland
Dec 26
PDX5:00 amPortland
3h 55m
MDW10:55 amChicago Midway
$218
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 October 24, 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

Thu 11/20

6:45 pm-1:08 pm

1 stop20h 23m

Portland

Mon 12/1

5:15 pm-7:43 am

2 stops36h 28m

$207

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Thu 12/4

8:50 am-12:54 pm

1 stop6h 04m

Portland

Sat 12/6

12:32 am-8:40 am

1 stop6h 08m

$208

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Fri 11/14

9:50 pm-12:20 am

Nonstop4h 30m

Portland

Tue 11/18

2:15 pm-10:55 pm

1 stop6h 40m

$209

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Sun 1/11

5:58 pm-8:31 pm

Nonstop4h 33m

Portland

Sun 2/1

6:00 am-12:15 pm

Nonstop4h 15m

$215

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Sat 12/6

2:05 pm-4:48 pm

Nonstop4h 43m

Portland

Sat 12/13

7:44 pm-6:21 am

1 stop8h 37m

$216

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Tue 1/13

1:55 pm-10:35 pm

1 stop10h 40m

Portland

Thu 1/15

5:35 am-5:00 pm

2 stops9h 25m

$216

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Wed 11/12

8:14 am-10:48 am

Nonstop4h 34m

Portland

Sat 11/15

1:26 pm-7:41 pm

Nonstop4h 15m

$217

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Fri 12/5

2:05 pm-4:48 pm

Nonstop4h 43m

Portland

Sun 12/7

2:37 pm-6:21 am

1 stop13h 44m

$226

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Sat 12/6

4:10 pm-6:45 pm

Nonstop4h 35m

Portland

Sat 12/13

11:59 pm-5:52 am

Nonstop3h 53m

$232

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Mon 1/26

4:15 pm-6:56 pm

Nonstop4h 41m

Portland

Wed 1/28

11:59 pm-6:00 am

Nonstop4h 01m

$241

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 $331. 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 Sunday, with ticket prices averaging around $412.

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 $325. At noon is when there is more demand to fly to Portland, so prices are often more expensive at around $478 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 $279 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.

Can stopping save me money on Chicago to Portland flights?

No. A direct flight is the cheapest option for a flight between Chicago to Portland.

How have Chicago to Portland flight prices changed over time?

As of October 2025, prices for Chicago to Portland flights are approximately 22% 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

$128

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 $128. The best round-trip flight deal from Chicago to Portland found on momondo in the last 72 hours is $268.
The fastest flight from Chicago to Portland takes 4h 20m
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 30m, 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
8,105 reviews
Search Spirit Airlines flights
FrontierPriceFrom $110Free CancellationRating
5.8
3,128 reviews
Search Frontier flights
DeltaPriceFrom $123Free CancellationRating
7.9
7,982 reviews
Search Delta flights
Hawaiian AirlinesPriceFrom $134Free CancellationRating
7.8
2,789 reviews
Search Hawaiian Airlines flights
Alaska AirlinesPriceFrom $196Free CancellationRating
8.0
11,161 reviews
Search Alaska Airlines flights
American AirlinesPriceFrom $213Free CancellationRating
7.2
11,033 reviews
Search American Airlines flights
United AirlinesPriceFrom $226Free CancellationRating
7.4
8,995 reviews
Search United Airlines flights
SouthwestPriceFrom $238Free CancellationRating
8.0
4,236 reviews
Search Southwest flights

  • Alaska Airlines Flights From Chicago to Portland

    Alaska Airlines flight deals from Chicago to Portland start from $196 round-trip. Over the 3 Alaska Airlines flights for this route in a normal week, average airfare is usually $298 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, 4,236 ratings). Southwest flies from Chicago to Portland around 10 times per week, with deals starting from $238 round-trip and rising to an average price of around $432.

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
The Dalles
Tigard
Pacific City
Manzanita
Tillamook

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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