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Cheap flights from Portland to Chicago from $106

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 11/9. 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 (PDX-ORD)

Cheap round-trip flights

Logo
12:07 pm - 9:32 pmPDX-ORD
7h 25m1 stop
Logo
6:00 am - 12:12 amORD-PDX
20h 12m1 stop
$176
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Wed, Sep 10 - Sun, Sep 14
Frontier Logo
6:05 am - 11:59 pmPDX-ORD
15h 54m1 stop
Frontier Logo
6:00 am - 12:12 amORD-PDX
20h 12m1 stop
$179Frontier
Find Deal
Thu, Sep 11 - Mon, Sep 15
Logo
12:43 pm - 11:53 pmPDX-ORD
9h 10m1 stop
Logo
6:35 am - 7:36 pmORD-PDX
15h 01m1 stop
$181
Find Deal
Wed, Oct 22 - Wed, Oct 29
Logo
8:36 pm - 12:31 pmPDX-ORD
13h 55m1 stop
Logo
6:00 am - 11:56 amORD-PDX
7h 56m1 stop
$182
Find Deal
Wed, Oct 29 - Mon, Nov 3
Frontier Logo
6:05 am - 9:37 amPDX-ORD
25h 32m1 stop
Frontier Logo
10:42 am - 12:12 amORD-PDX
15h 30m1 stop
$184Frontier
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Sun, Sep 28 - Sun, Oct 5
Hawaiian Airlines Logo
11:00 pm - 5:01 amPDX-ORD
4h 01mnonstop
Hawaiian Airlines Logo
7:00 am - 9:39 amORD-PDX
4h 39mnonstop
$214Hawaiian Airlines
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Fri, Oct 31 - Mon, Nov 3
United Airlines Logo
8:30 am - 2:38 pmPDX-ORD
4h 08mnonstop
United Airlines Logo
7:55 pm - 10:30 pmORD-PDX
4h 35mnonstop
$227United Airlines
Find Deal
Wed, Sep 24 - Tue, Sep 30
American Airlines Logo
1:40 pm - 7:49 pmPDX-ORD
4h 09mnonstop
American Airlines Logo
7:25 am - 9:47 amORD-PDX
4h 22mnonstop
$229American Airlines
Find Deal
Tue, Sep 16 - Wed, Oct 1
American Airlines Logo
11:18 am - 5:28 pmPDX-ORD
4h 10mnonstop
American Airlines Logo
8:05 am - 10:28 amORD-PDX
4h 23mnonstop
$231American Airlines
Find Deal
Tue, Sep 16 - Sat, Sep 20
Alaska Airlines Logo
10:55 pm - 5:00 amPDX-ORD
4h 05mnonstop
Alaska Airlines Logo
7:00 am - 9:25 amORD-PDX
4h 25mnonstop
$232Alaska Airlines
Find Deal
Fri, Sep 26 - Sat, Sep 27

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
Sep 11
PDX6:05 amPortland
15h 54m
1 stop
ORD11:59 pmChicago O'Hare Intl
Sep 15
ORD6:00 amChicago O'Hare Intl
20h 12m
1 stop
PDX12:12 amPortland
$179
Find similar
Frontier
Sep 7
PDX10:27 amPortland
10h 13m
1 stop
ORD10:40 pmChicago O'Hare Intl
Sep 10
ORD7:20 amChicago O'Hare Intl
17h 14m
1 stop
PDX10:34 pmPortland
$181
Find similar
Frontier
Sep 28
PDX6:05 amPortland
25h 32m
1 stop
ORD9:37 amChicago O'Hare Intl
Oct 5
ORD10:42 amChicago O'Hare Intl
15h 30m
1 stop
PDX12:12 amPortland
$184
Find similar

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

Our best Spirit Airlines deals on Portland to Chicago O'Hare Intl Airport flight tickets
Spirit Airlines
Aug 30
PDX7:52 pmPortland
13h 51m
1 stop
ORD11:43 amChicago O'Hare Intl
Sep 5
ORD6:15 amChicago O'Hare Intl
6h 56m
1 stop
PDX11:11 amPortland
$195
Find similar
Spirit Airlines
Sep 17
PDX12:07 pmPortland
7h 25m
1 stop
ORD9:32 pmChicago O'Hare Intl
Sep 19
ORD6:15 amChicago O'Hare Intl
6h 56m
1 stop
PDX11:11 amPortland
$216
Find similar
Spirit Airlines
Sep 10
PDX12:07 pmPortland
7h 25m
1 stop
ORD9:32 pmChicago O'Hare Intl
Sep 16
ORD5:05 amChicago O'Hare Intl
32h 06m
3 stops
PDX11:11 amPortland
$228
Find similar

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 August 26, 2025.
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

PortlandChicago

PDX - ORD

PDXORD

Portland

Wed 9/10

12:07 pm-9:32 pm

1 stop7h 25m

Chicago O'Hare Intl

Sun 9/14

6:00 am-12:12 am

1 stop20h 12m

$176

PortlandChicago

PDX - ORD

PDXORD

Portland

Thu 9/11

6:05 am-11:59 pm

1 stop15h 54m

Chicago O'Hare Intl

Mon 9/15

6:00 am-12:12 am

1 stop20h 12m

$179

PortlandChicago

PDX - ORD

PDXORD

Portland

Wed 10/22

12:43 pm-11:53 pm

1 stop9h 10m

Chicago O'Hare Intl

Wed 10/29

6:35 am-7:36 pm

1 stop15h 01m

$181

PortlandChicago

PDX - ORD

PDXORD

Portland

Wed 10/29

8:36 pm-12:31 pm

1 stop13h 55m

Chicago O'Hare Intl

Mon 11/3

6:00 am-11:56 am

1 stop7h 56m

$182

PortlandChicago

PDX - ORD

PDXORD

Portland

Sun 9/28

6:05 am-9:37 am

1 stop25h 32m

Chicago O'Hare Intl

Sun 10/5

10:42 am-12:12 am

1 stop15h 30m

$184

PortlandChicago

PDX - ORD

PDXORD

Portland

Fri 10/31

11:00 pm-5:01 am

Nonstop4h 01m

Chicago O'Hare Intl

Mon 11/3

7:00 am-9:39 am

Nonstop4h 39m

$214

PortlandChicago

PDX - ORD

PDXORD

Portland

Wed 9/24

8:30 am-2:38 pm

Nonstop4h 08m

Chicago O'Hare Intl

Tue 9/30

7:55 pm-10:30 pm

Nonstop4h 35m

$227

PortlandChicago

PDX - ORD

PDXORD

Portland

Tue 9/16

1:40 pm-7:49 pm

Nonstop4h 09m

Chicago O'Hare Intl

Wed 10/1

7:25 am-9:47 am

Nonstop4h 22m

$229

PortlandChicago

PDX - ORD

PDXORD

Portland

Tue 9/16

11:18 am-5:28 pm

Nonstop4h 10m

Chicago O'Hare Intl

Sat 9/20

8:05 am-10:28 am

Nonstop4h 23m

$231

PortlandChicago

PDX - ORD

PDXORD

Portland

Fri 9/26

10:55 pm-5:00 am

Nonstop4h 05m

Chicago O'Hare Intl

Sat 9/27

7:00 am-9:25 am

Nonstop4h 25m

$232

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 January is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Portland averaging around $287.

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 Friday when prices can be found for as low as $458. This is often the case because there is less demand to fly during this day of the week. On the other hand, Sunday 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 $579.

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 $310 when looking at flights departing in the afternoon. Try not to purchase tickets in the morning because they tend to be around $531. 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 $358 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 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 9% 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 August 2025, prices for Portland to Chicago O'Hare Intl Airport flights are approximately 45% 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

$174

Fastest flight time

3h 53m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Portland in the past 72 hours is $174. The best round-trip flight deal from Portland to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $321.
The fastest flight from Portland to Chicago O'Hare Intl Airport takes 3h 53m
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 4h 01m, 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 $98Free CancellationRating
6.3
8,031 reviews
Search Spirit Airlines flights
FrontierPriceFrom $108Free CancellationRating
5.8
3,200 reviews
Search Frontier flights
DeltaPriceFrom $123Free CancellationRating
7.9
7,979 reviews
Search Delta flights
Hawaiian AirlinesPriceFrom $125Free CancellationRating
7.8
2,681 reviews
Search Hawaiian Airlines flights
Alaska AirlinesPriceFrom $195Free CancellationRating
8.0
10,000 reviews
Search Alaska Airlines flights
American AirlinesPriceFrom $197Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $224Free CancellationRating
7.4
8,943 reviews
Search United 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 $342, with the best Alaska Airlines deals starting from $195 round-trip. 10,000 users have rated Alaska Airlines on momondo, with an average score of 8.0/10.

  • 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 $286 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. 2,681 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
Rockford
South Haven
Schaumburg
Merrillville
Gurnee
Naperville
Rosemont
Kenosha
New Buffalo
Joliet
Oak Brook
Racine
Hammond
Tinley Park
Orland Park
Elgin
Aurora
Janesville
Benton Harbor

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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