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Cheap flights from Portland to Chicago from $109

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 5/14. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Portland to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
2:35 pm - 11:55 pm
PDX
-
ORD
7h 20m
1 stop
Southwest Logo
4:50 pm - 11:10 pm
ORD
-
PDX
8h 20m
1 stop
$222Southwest
Tue, Apr 14 - Tue, Apr 21
Frontier Logo
9:54 am - 5:50 am
PDX
-
ORD
17h 56m
1 stop
Frontier Logo
7:21 pm - 11:50 am
ORD
-
PDX
18h 29m
1 stop
$223Frontier
Fri, Apr 17 - Wed, Apr 22
Southwest Logo
11:45 am - 10:55 pm
PDX
-
ORD
9h 10m
2 stops
Southwest Logo
4:50 pm - 11:10 pm
ORD
-
PDX
8h 20m
1 stop
$227Southwest
Tue, Apr 14 - Tue, Apr 21
Frontier Logo
12:27 pm - 9:45 am
PDX
-
ORD
19h 18m
1 stop
Frontier Logo
7:21 pm - 11:50 am
ORD
-
PDX
18h 29m
1 stop
$231Frontier
Sat, Apr 18 - Sat, Apr 25
United Airlines Logo
11:59 pm - 6:03 am
PDX
-
ORD
4h 04mnonstop
United Airlines Logo
8:00 pm - 10:34 pm
ORD
-
PDX
4h 34mnonstop
$235United Airlines
Thu, Apr 16 - Mon, Apr 20
American Airlines Logo
1:45 pm - 8:11 pm
PDX
-
ORD
4h 26mnonstop
American Airlines Logo
7:29 am - 9:59 am
ORD
-
PDX
4h 30mnonstop
$236American Airlines
Thu, Jun 4 - Wed, Jun 10
American Airlines Logo
11:47 pm - 5:49 am
PDX
-
ORD
4h 02mnonstop
American Airlines Logo
8:19 pm - 10:56 pm
ORD
-
PDX
4h 37mnonstop
$237American Airlines
Thu, Apr 23 - Wed, Apr 29
Frontier Logo
5:31 pm - 6:39 am
PDX
-
ORD
11h 08m
1 stop
Frontier Logo
8:56 pm - 11:50 am
ORD
-
PDX
16h 54m
1 stop
$238Frontier
Fri, May 8 - Sun, May 10
Frontier Logo
1:48 pm - 3:17 pm
PDX
-
ORD
23h 29m
2 stops
Frontier Logo
8:58 pm - 8:59 am
ORD
-
PDX
14h 01m
1 stop
$239Frontier
Tue, Apr 14 - Sun, Apr 19
Frontier Logo
11:48 am - 4:52 pm
PDX
-
ORD
51h 04m
2 stops
Frontier Logo
7:21 pm - 11:50 am
ORD
-
PDX
18h 29m
1 stop
$240Frontier
Mon, Apr 27 - Sat, May 2

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

Our best American Airlines deals on Portland to Chicago O'Hare Intl Airport flight tickets
American Airlines
Jun 4
PDX1:45 pmPortland
4h 26m
ORD8:11 pmChicago O'Hare Intl
Jun 10
ORD7:29 amChicago O'Hare Intl
4h 30m
PDX9:59 amPortland
$236
American Airlines
Apr 23
PDX11:47 pmPortland
4h 02m
ORD5:49 amChicago O'Hare Intl
Apr 29
ORD8:19 pmChicago O'Hare Intl
4h 37m
PDX10:56 pmPortland
$237
American Airlines
Apr 18
PDX3:16 pmPortland
4h 18m
ORD9:34 pmChicago O'Hare Intl
Apr 25
ORD8:20 pmChicago O'Hare Intl
4h 37m
PDX10:57 pmPortland
$253

Southwest flights from Portland to Chicago O'Hare Intl Airport

Our best Southwest deals on Portland to Chicago O'Hare Intl Airport flight tickets
Southwest
Apr 14
PDX2:35 pmPortland
7h 20m
1 stop
ORD11:55 pmChicago O'Hare Intl
Apr 21
ORD4:50 pmChicago O'Hare Intl
8h 20m
1 stop
PDX11:10 pmPortland
$222
Southwest
Apr 14
PDX11:45 amPortland
9h 10m
2 stops
ORD10:55 pmChicago O'Hare Intl
Apr 21
ORD4:50 pmChicago O'Hare Intl
8h 20m
1 stop
PDX11:10 pmPortland
$227
Southwest
Apr 15
PDX2:35 pmPortland
7h 20m
1 stop
ORD11:55 pmChicago O'Hare Intl
Apr 22
ORD11:55 amChicago O'Hare Intl
12h 05m
2 stops
PDX10:00 pmPortland
$248

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 March 25, 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

Tue 4/14

2:35 pm-11:55 pm

1 stop7h 20m

Chicago O'Hare Intl

Tue 4/21

4:50 pm-11:10 pm

1 stop8h 20m

$222

PortlandChicago

PDX - ORD

PDXORD

Portland

Fri 4/17

9:54 am-5:50 am

1 stop17h 56m

Chicago O'Hare Intl

Wed 4/22

7:21 pm-11:50 am

1 stop18h 29m

$223

PortlandChicago

PDX - ORD

PDXORD

Portland

Tue 4/14

11:45 am-10:55 pm

2 stops9h 10m

Chicago O'Hare Intl

Tue 4/21

4:50 pm-11:10 pm

1 stop8h 20m

$227

PortlandChicago

PDX - ORD

PDXORD

Portland

Sat 4/18

12:27 pm-9:45 am

1 stop19h 18m

Chicago O'Hare Intl

Sat 4/25

7:21 pm-11:50 am

1 stop18h 29m

$231
Quickest round-trip

PortlandChicago

PDX - ORD

PDXORD

Portland

Thu 4/16

11:59 pm-6:03 am

Nonstop4h 04m

Chicago O'Hare Intl

Mon 4/20

8:00 pm-10:34 pm

Nonstop4h 34m

$235

PortlandChicago

PDX - ORD

PDXORD

Portland

Thu 6/4

1:45 pm-8:11 pm

Nonstop4h 26m

Chicago O'Hare Intl

Wed 6/10

7:29 am-9:59 am

Nonstop4h 30m

$236

PortlandChicago

PDX - ORD

PDXORD

Portland

Thu 4/23

11:47 pm-5:49 am

Nonstop4h 02m

Chicago O'Hare Intl

Wed 4/29

8:19 pm-10:56 pm

Nonstop4h 37m

$237

PortlandChicago

PDX - ORD

PDXORD

Portland

Fri 5/8

5:31 pm-6:39 am

1 stop11h 08m

Chicago O'Hare Intl

Sun 5/10

8:56 pm-11:50 am

1 stop16h 54m

$238

PortlandChicago

PDX - ORD

PDXORD

Portland

Tue 4/14

1:48 pm-3:17 pm

2 stops23h 29m

Chicago O'Hare Intl

Sun 4/19

8:58 pm-8:59 am

1 stop14h 01m

$239

PortlandChicago

PDX - ORD

PDXORD

Portland

Mon 4/27

11:48 am-4:52 pm

2 stops51h 04m

Chicago O'Hare Intl

Sat 5/2

7:21 pm-11:50 am

1 stop18h 29m

$240

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 cheapest month to fly to Chicago O'Hare Intl Airport?

The month of August is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Portland averaging around $283.

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 $422. 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 $548.

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 $305 when looking at flights departing in the afternoon. Try not to purchase tickets in the morning because they tend to be around $480. 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 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 $338 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 $270 on momondo.

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

There are 4 cabin classes available to choose from on Portland to Chicago O'Hare Intl 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 19% 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 March 2026, prices for Portland to Chicago O'Hare Intl Airport flights are approximately 19% cheaper 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

$173

Fastest flight time

3h 54m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Portland in the past 72 hours is $173. The best round-trip flight deal from Portland to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $347.
The fastest flight from Portland to Chicago O'Hare Intl Airport takes 3h 54m
Direct flights go from Portland to Chicago O'Hare Intl Airport every day.
Search flight deals

  • 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 54m, 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
Spirit AirlinesPriceFrom $93Free CancellationRating
6.3
8,541 reviews
Search Spirit Airlines flights
FrontierPriceFrom $96Free CancellationRating
5.7
3,017 reviews
Search Frontier flights
DeltaPriceFrom $99Free CancellationRating
7.9
8,326 reviews
Search Delta flights
Hawaiian AirlinesPriceFrom $125Free CancellationRating
7.8
2,840 reviews
Search Hawaiian Airlines flights
American AirlinesPriceFrom $179Free CancellationRating
7.1
11,494 reviews
Search American Airlines flights
United AirlinesPriceFrom $206Free CancellationRating
7.4
9,477 reviews
Search United Airlines flights
Alaska AirlinesPriceFrom $208Free CancellationRating
7.9
12,111 reviews
Search Alaska Airlines flights

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

    Across 5 Alaska Airlines flights from Portland to Chicago O'Hare Intl Airport this week, the average price was $336, with the best Alaska Airlines deals starting from $208 round-trip. 12,107 users have rated Alaska Airlines on momondo, with an average score of 7.9/10.

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

    The best Hawaiian Airlines deal for Portland to Chicago O'Hare Intl Airport flight tickets found on momondo in the last 72 hours was $125, round-trip. It should be noted that an average Hawaiian Airlines flight deal for this route in this time was higher, at $271 round-trip. Hawaiian Airlines operates 7 flights out of Portland into Chicago O'Hare Intl Airport in an average week, so prices vary by time and availability. 2,840 Hawaiian Airlines reviews by users on momondo have scored the airline at 7.8/10.

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
New Buffalo
Orland Park
Kenosha
Oak Brook
Joliet
Janesville
Racine
Hammond
Aurora
Elgin
Tinley Park
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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