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Cheap flights from Portland to Chicago from $159

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Portland to Chicago departing on 7/14. 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
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Portland to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
5:49 pm - 5:37 am
PDX
-
ORD
9h 48m
1 stop
Frontier Logo
9:57 pm - 4:36 pm
ORD
-
PDX
20h 39m
1 stop
$322Frontier
Fri, Jul 10 - Tue, Jul 14
Frontier Logo
5:16 pm - 8:52 pm
PDX
-
ORD
25h 36m
1 stop
Frontier Logo
9:13 pm - 11:35 am
ORD
-
PDX
16h 22m
1 stop
$323Frontier
Tue, Jul 14 - Sat, Aug 1
Frontier Logo
3:47 pm - 10:01 am
PDX
-
ORD
16h 14m
1 stop
Frontier Logo
10:40 pm - 4:35 pm
ORD
-
PDX
19h 55m
1 stop
$324Frontier
Fri, Oct 30 - Sun, Nov 1
American Airlines Logo
11:15 pm - 5:14 am
PDX
-
ORD
3h 59mnonstop
American Airlines Logo
10:15 pm - 12:50 am
ORD
-
PDX
4h 35mnonstop
$325American Airlines
Wed, Jul 15 - Wed, Jul 22
Frontier Logo
5:21 pm - 8:52 pm
PDX
-
ORD
25h 31m
1 stop
Frontier Logo
7:29 am - 4:54 pm
ORD
-
PDX
11h 25m
1 stop
$326Frontier
Wed, Aug 12 - Mon, Aug 17
Multiple Airlines Logo
10:59 pm - 5:00 am
PDX
-
ORD
4h 01mnonstop
Multiple Airlines Logo
9:57 pm - 4:51 pm
ORD
-
PDX
20h 54m
1 stop
$327Multiple Airlines
Wed, Jul 15 - Wed, Jul 22
Frontier Logo
5:49 pm - 5:37 am
PDX
-
ORD
9h 48m
1 stop
Frontier Logo
7:15 am - 4:54 pm
ORD
-
PDX
11h 39m
1 stop
$328Frontier
Fri, Jul 17 - Fri, Jul 24
Frontier Logo
6:49 pm - 5:37 am
PDX
-
ORD
8h 48m
1 stop
Frontier Logo
9:57 pm - 4:51 pm
ORD
-
PDX
20h 54m
1 stop
$329Frontier
Sun, Jul 26 - Thu, Jul 30
Multiple Airlines Logo
6:49 pm - 5:37 am
PDX
-
ORD
8h 48m
1 stop
Multiple Airlines Logo
7:20 am - 9:45 am
ORD
-
PDX
4h 25mnonstop
$330Multiple Airlines
Thu, Jul 23 - Mon, Jul 27
Multiple Airlines Logo
10:59 pm - 5:00 am
PDX
-
ORD
4h 01mnonstop
Multiple Airlines Logo
9:57 pm - 4:51 pm
ORD
-
PDX
20h 54m
1 stop
$331Multiple Airlines
Tue, Jul 21 - Wed, Jul 29

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Alaska Airlines flights from Portland to Chicago O'Hare Intl Airport

Our best Alaska Airlines deals on Portland to Chicago O'Hare Intl Airport flight tickets
Alaska Airlines
Aug 4
PDX10:59 pmPortland
4h 01m
ORD5:00 amChicago O'Hare Intl
Aug 8
ORD8:20 pmChicago O'Hare Intl
13h 17m
1 stop
PDX7:37 amPortland
$335
Alaska Airlines
Jul 18
PDX10:59 pmPortland
4h 01m
ORD5:00 amChicago O'Hare Intl
Jul 25
ORD7:20 amChicago O'Hare Intl
4h 25m
PDX9:45 amPortland
$341
Alaska Airlines
Jul 4
PDX12:13 pmPortland
4h 06m
ORD6:19 pmChicago O'Hare Intl
Jul 14
ORD7:20 amChicago O'Hare Intl
4h 25m
PDX9:45 amPortland
$342

Frontier flights from Portland to Chicago O'Hare Intl Airport

Our best Frontier deals on Portland to Chicago O'Hare Intl Airport flight tickets
Frontier
Jul 10
PDX5:49 pmPortland
9h 48m
1 stop
ORD5:37 amChicago O'Hare Intl
Jul 14
ORD9:57 pmChicago O'Hare Intl
20h 39m
1 stop
PDX4:36 pmPortland
$322
Frontier
Jul 14
PDX5:16 pmPortland
25h 36m
1 stop
ORD8:52 pmChicago O'Hare Intl
Aug 1
ORD9:13 pmChicago O'Hare Intl
16h 22m
1 stop
PDX11:35 amPortland
$323
Frontier
Oct 30
PDX3:47 pmPortland
16h 14m
1 stop
ORD10:01 amChicago O'Hare Intl
Nov 1
ORD10:40 pmChicago O'Hare Intl
19h 55m
1 stop
PDX4:35 pmPortland
$324

momondo Fare Finder

 
Customize your flight search to find flights from Portland to Chicago O'Hare Intl Airport 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 June 24, 2026.
Use the filters below to find and compare flights from Portland to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

PortlandChicago

PDX - ORD

PDXORD

Portland

Fri 7/10

5:49 pm-5:37 am

1 stop9h 48m

Chicago O'Hare Intl

Tue 7/14

9:57 pm-4:36 pm

1 stop20h 39m

$322

PortlandChicago

PDX - ORD

PDXORD

Portland

Tue 7/14

5:16 pm-8:52 pm

1 stop25h 36m

Chicago O'Hare Intl

Sat 8/1

9:13 pm-11:35 am

1 stop16h 22m

$323

PortlandChicago

PDX - ORD

PDXORD

Portland

Fri 10/30

3:47 pm-10:01 am

1 stop16h 14m

Chicago O'Hare Intl

Sun 11/1

10:40 pm-4:35 pm

1 stop19h 55m

$324
Quickest round-trip

PortlandChicago

PDX - ORD

PDXORD

Portland

Wed 7/15

11:15 pm-5:14 am

Nonstop3h 59m

Chicago O'Hare Intl

Wed 7/22

10:15 pm-12:50 am

Nonstop4h 35m

$325

PortlandChicago

PDX - ORD

PDXORD

Portland

Wed 8/12

5:21 pm-8:52 pm

1 stop25h 31m

Chicago O'Hare Intl

Mon 8/17

7:29 am-4:54 pm

1 stop11h 25m

$326

PortlandChicago

PDX - ORD

PDXORD

Portland

Wed 7/15

10:59 pm-5:00 am

Nonstop4h 01m

Chicago O'Hare Intl

Wed 7/22

9:57 pm-4:51 pm

1 stop20h 54m

$327

PortlandChicago

PDX - ORD

PDXORD

Portland

Fri 7/17

5:49 pm-5:37 am

1 stop9h 48m

Chicago O'Hare Intl

Fri 7/24

7:15 am-4:54 pm

1 stop11h 39m

$328

PortlandChicago

PDX - ORD

PDXORD

Portland

Sun 7/26

6:49 pm-5:37 am

1 stop8h 48m

Chicago O'Hare Intl

Thu 7/30

9:57 pm-4:51 pm

1 stop20h 54m

$329

PortlandChicago

PDX - ORD

PDXORD

Portland

Thu 7/23

6:49 pm-5:37 am

1 stop8h 48m

Chicago O'Hare Intl

Mon 7/27

7:20 am-9:45 am

Nonstop4h 25m

$330

PortlandChicago

PDX - ORD

PDXORD

Portland

Tue 7/21

10:59 pm-5:00 am

Nonstop4h 01m

Chicago O'Hare Intl

Wed 7/29

9:57 pm-4:51 pm

1 stop20h 54m

$331

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 Chicago from

How to get the cheapest flight ticket from Portland to Chicago O'Hare Intl Airport

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 Portland and Chicago O'Hare Intl Airport?

What is the cheapest month to fly to Chicago O'Hare Intl Airport?

The month of September is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Portland averaging around $304.

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Wednesday when prices can be found for as low as $426. This is often the case because there is less demand to fly during this day of the week. On the other hand, Monday is the most expensive day to depart from Portland because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $535.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

Flying to Chicago O'Hare Intl Airport from Portland in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $360 when looking at flights departing in the afternoon. Try not to purchase tickets in the morning because they tend to be around $483. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Portland to Chicago O'Hare Intl flight route?

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

How far in advance should I book a flight from Portland to Chicago O'Hare Intl Airport?

You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from Portland when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around $350 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago O'Hare Intl Airport from Portland for as low as $298 on momondo.

What cabin class options are available on Portland to Chicago O'Hare Intl Airport flights?

There are 4 cabin classes available to choose from on Portland to Chicago O'Hare Intl Airport 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 Portland to Chicago O'Hare Intl Airport flights?

You could potentially save up to 29% on your flight if you consider stops on a Portland to Chicago O'Hare Intl Airport flight.

How have Portland to Chicago O'Hare Intl Airport flight prices changed over time?

As of June 2026, prices for Portland to Chicago O'Hare Intl Airport flights are approximately 125% more expensive when compared to flights at the same time last year.

When to book flights from Portland to Chicago O'Hare Intl Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Portland to Chicago O'Hare Intl Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Portland to Chicago O'Hare Intl Airport (PDX to ORD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Portland to Chicago O'Hare Intl Airport

Best Price Found

$219

Fastest flight time

3h 58m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Portland in the past 72 hours is $219. The best round-trip flight deal from Portland to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $398.
The fastest flight from Portland to Chicago O'Hare Intl Airport takes 3h 58m
Direct flights go from Portland to Chicago O'Hare Intl Airport every day.
Search flight deals

Frequently asked questions about flying from Portland to Chicago O'Hare Intl Airport

  • How far is Portland to Chicago O'Hare Intl by plane?

    Portland and Chicago O'Hare Intl are 1737.6 mi apart from one another. Flights usually cover this in 3h 58m, depending on flying conditions and air traffic around both airports.

  • When did momondo last update prices for flights from Portland Airport to Chicago O'Hare Intl Airport?

    Prices for flights from Portland Airport to Chicago O'Hare Intl Airport are refreshed on a daily basis.

  • How many operators does momondo search for flights from Portland Airport to Chicago O'Hare Intl Airport?

  • How old do you have to be to fly from Portland Airport to Chicago O'Hare Intl Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Portland Airport to Chicago O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The travel and health documents required for your trip to Chicago O'Hare Intl 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 Chicago O'Hare Intl 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 Portland to Chicago O'Hare Intl Airport?

  • What is the most popular airline from Portland to Chicago O'Hare Intl Airport?

Best airlines flying from Portland to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from Portland to Chicago O'Hare Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
Hawaiian AirlinesPriceFrom $93Free CancellationRating
7.8
2,826 reviews
Search Hawaiian Airlines flights
FrontierPriceFrom $96Free CancellationRating
5.6
2,866 reviews
Search Frontier flights
DeltaPriceFrom $125Free CancellationRating
7.8
8,435 reviews
Search Delta flights
American AirlinesPriceFrom $173Free CancellationRating
7.1
11,754 reviews
Search American Airlines flights
Alaska AirlinesPriceFrom $207Free CancellationRating
7.9
12,573 reviews
Search Alaska Airlines flights
United AirlinesPriceFrom $221Free CancellationRating
7.4
9,887 reviews
Search United Airlines flights

  • Alaska Airlines Flights From Portland to Chicago O'Hare Intl Airport

    Across 10 Alaska Airlines flights from Portland to Chicago O'Hare Intl Airport this week, the average price was $365, with the best Alaska Airlines deals starting from $207 round-trip. 12,573 users have rated Alaska Airlines on momondo, with an average score of 7.9/10.

  • United Airlines Flights From Portland to Chicago O'Hare Intl Airport

    The best United Airlines deal for Portland to Chicago O'Hare Intl Airport flight tickets found on momondo in the last 72 hours was $221, round-trip. It should be noted that an average United Airlines flight deal for this route in this time was higher, at $381 round-trip. United Airlines operates 18 flights out of Portland into Chicago O'Hare Intl Airport in an average week, so prices vary by time and availability. 9,887 United Airlines reviews by users on momondo have scored the airline at 7.4/10.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lake Geneva
Schaumburg
South Haven
Rockford
Merrillville
Gurnee
Rosemont
Naperville
Orland Park
Oak Brook
New Buffalo
Joliet
Kenosha
Hammond
Aurora
Racine
Janesville
Elgin
Evanston
South Holland

Why use momondo?

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

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Portland.

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

Yes. momondo allows you to filter the results for Portland to Chicago flights to just show those with flexible booking policies.

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

momondo provides multiple filters to help you find the best flight to Chicago from Portland. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

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

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Portland and alert you when they change.

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