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Cheap flights from Portland to Chicago 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 Portland to Chicago departing on 3/8. 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

Enter your travel dates to find the best prices.
Alaska Airlines Logo
11:00 pm - 5:02 am
PDX
-
ORD
4h 02mnonstop
Alaska Airlines Logo
3:37 pm - 10:04 pm
ORD
-
PDX
8h 27m1 stop
$236Alaska Airlines
Thu, Jan 1 - Mon, Jan 5
Alaska Airlines Logo
5:10 am - 2:41 pm
PDX
-
ORD
7h 31m1 stop
Alaska Airlines Logo
2:06 pm - 4:48 pm
ORD
-
PDX
4h 42mnonstop
$237Alaska Airlines
Mon, Jan 5 - Sun, Jan 18
United Airlines Logo
1:24 pm - 9:15 pm
PDX
-
ORD
5h 51m1 stop
United Airlines Logo
8:45 am - 2:46 pm
ORD
-
PDX
8h 01m1 stop
$242United Airlines
Thu, Jan 22 - Sat, Jan 31
United Airlines Logo
11:55 pm - 5:56 am
PDX
-
ORD
4h 01mnonstop
United Airlines Logo
7:58 pm - 10:40 pm
ORD
-
PDX
4h 42mnonstop
$243United Airlines
Tue, Dec 30 - Mon, Jan 5
Alaska Airlines Logo
8:30 am - 4:33 pm
PDX
-
ORD
6h 03m1 stop
Alaska Airlines Logo
5:29 pm - 10:41 pm
ORD
-
PDX
7h 12m1 stop
$246Alaska Airlines
Thu, Feb 12 - Tue, Feb 17
Delta Logo
9:45 pm - 8:43 am
PDX
-
ORD
8h 58m1 stop
Delta Logo
7:20 am - 12:32 pm
ORD
-
PDX
7h 12m1 stop
$247Delta
Mon, Jan 5 - Sun, Jan 18
Alaska Airlines Logo
6:00 am - 2:11 pm
PDX
-
ORD
6h 11m1 stop
Alaska Airlines Logo
5:29 pm - 10:41 pm
ORD
-
PDX
7h 12m1 stop
$251Alaska Airlines
Thu, Feb 12 - Thu, Feb 12
Alaska Airlines Logo
7:18 am - 11:37 pm
PDX
-
ORD
14h 19m1 stop
Alaska Airlines Logo
8:00 am - 12:38 pm
ORD
-
PDX
6h 38m1 stop
$252Alaska Airlines
Sun, Jan 11 - Wed, Jan 14
United Airlines Logo
11:55 pm - 5:56 am
PDX
-
ORD
4h 01mnonstop
United Airlines Logo
2:31 pm - 9:07 pm
ORD
-
PDX
8h 36m1 stop
$253United Airlines
Tue, Dec 30 - Mon, Jan 5
Multiple Airlines Logo
11:00 pm - 5:02 am
PDX
-
ORD
4h 02mnonstop
Multiple Airlines Logo
6:15 am - 4:16 pm
ORD
-
PDX
12h 01m1 stop
$255Multiple Airlines
Sun, Jan 4 - Sun, Jan 11

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
Jan 1
PDX11:00 pmPortland
4h 02m
ORD5:02 amChicago O'Hare Intl
Jan 5
ORD3:37 pmChicago O'Hare Intl
8h 27m
1 stop
PDX10:04 pmPortland
$236
Find similar
Alaska Airlines
Jan 5
PDX7:07 amPortland
4h 09m
ORD1:16 pmChicago O'Hare Intl
Jan 12
ORD2:06 pmChicago O'Hare Intl
4h 42m
PDX4:48 pmPortland
$237
Find similar
Alaska Airlines
Jan 17
PDX1:38 pmPortland
8h 12m
1 stop
ORD11:50 pmChicago O'Hare Intl
Jan 18
ORD8:00 amChicago O'Hare Intl
6h 38m
1 stop
PDX12:38 pmPortland
$243
Find similar

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

Our best United Airlines deals on Portland to Chicago O'Hare Intl Airport flight tickets
United Airlines
Jan 22
PDX1:24 pmPortland
5h 51m
1 stop
ORD9:15 pmChicago O'Hare Intl
Jan 31
ORD8:45 amChicago O'Hare Intl
8h 01m
1 stop
PDX2:46 pmPortland
$242
Find similar
United Airlines
Feb 25
PDX1:18 pmPortland
6h 11m
1 stop
ORD9:29 pmChicago O'Hare Intl
Mar 1
ORD5:50 pmChicago O'Hare Intl
7h 09m
1 stop
PDX10:59 pmPortland
$265
Find similar
United Airlines
Dec 25
PDX7:10 amPortland
4h 05m
ORD1:15 pmChicago O'Hare Intl
Jan 4
ORD8:02 pmChicago O'Hare Intl
4h 41m
PDX10:43 pmPortland
$275
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 December 8, 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

Thu 1/1

11:00 pm-5:02 am

Nonstop4h 02m

Chicago O'Hare Intl

Mon 1/5

3:37 pm-10:04 pm

1 stop8h 27m

$236

PortlandChicago

PDX - ORD

PDXORD

Portland

Mon 1/5

5:10 am-2:41 pm

1 stop7h 31m

Chicago O'Hare Intl

Sun 1/18

2:06 pm-4:48 pm

Nonstop4h 42m

$237

PortlandChicago

PDX - ORD

PDXORD

Portland

Thu 1/22

1:24 pm-9:15 pm

1 stop5h 51m

Chicago O'Hare Intl

Sat 1/31

8:45 am-2:46 pm

1 stop8h 01m

$242

PortlandChicago

PDX - ORD

PDXORD

Portland

Tue 12/30

11:55 pm-5:56 am

Nonstop4h 01m

Chicago O'Hare Intl

Mon 1/5

7:58 pm-10:40 pm

Nonstop4h 42m

$243

PortlandChicago

PDX - ORD

PDXORD

Portland

Thu 2/12

8:30 am-4:33 pm

1 stop6h 03m

Chicago O'Hare Intl

Tue 2/17

5:29 pm-10:41 pm

1 stop7h 12m

$246

PortlandChicago

PDX - ORD

PDXORD

Portland

Mon 1/5

9:45 pm-8:43 am

1 stop8h 58m

Chicago O'Hare Intl

Sun 1/18

7:20 am-12:32 pm

1 stop7h 12m

$247

PortlandChicago

PDX - ORD

PDXORD

Portland

Thu 2/12

6:00 am-2:11 pm

1 stop6h 11m

Chicago O'Hare Intl

Thu 2/12

5:29 pm-10:41 pm

1 stop7h 12m

$251

PortlandChicago

PDX - ORD

PDXORD

Portland

Sun 1/11

7:18 am-11:37 pm

1 stop14h 19m

Chicago O'Hare Intl

Wed 1/14

8:00 am-12:38 pm

1 stop6h 38m

$252

PortlandChicago

PDX - ORD

PDXORD

Portland

Tue 12/30

11:55 pm-5:56 am

Nonstop4h 01m

Chicago O'Hare Intl

Mon 1/5

2:31 pm-9:07 pm

1 stop8h 36m

$253

PortlandChicago

PDX - ORD

PDXORD

Portland

Sun 1/4

11:00 pm-5:02 am

Nonstop4h 02m

Chicago O'Hare Intl

Sun 1/11

6:15 am-4:16 pm

1 stop12h 01m

$255

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 $301.

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 $432. 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 $555.

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 $318 when looking at flights departing in the afternoon. Try not to purchase tickets in the morning because they tend to be around $505. 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 $353 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 $293 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?

No. A direct flight is the cheapest option for a flight between Portland to Chicago O'Hare Intl Airport.

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

As of December 2025, prices for Portland to Chicago O'Hare Intl Airport flights are approximately 27% 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

$179

Fastest flight time

3h 44m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Portland in the past 72 hours is $179. The best round-trip flight deal from Portland to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $348.
The fastest flight from Portland to Chicago O'Hare Intl Airport takes 3h 44m
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
FrontierPriceFrom $96Free CancellationRating
5.8
3,088 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $119Free CancellationRating
6.3
8,168 reviews
Search Spirit Airlines flights
DeltaPriceFrom $123Free CancellationRating
7.9
8,012 reviews
Search Delta flights
Hawaiian AirlinesPriceFrom $125Free CancellationRating
7.8
2,818 reviews
Search Hawaiian Airlines flights
American AirlinesPriceFrom $194Free CancellationRating
7.2
11,042 reviews
Search American Airlines flights
Alaska AirlinesPriceFrom $217Free CancellationRating
8.0
11,413 reviews
Search Alaska Airlines flights
United AirlinesPriceFrom $221Free CancellationRating
7.4
9,076 reviews
Search United Airlines flights

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

    Across 4 Alaska Airlines flights from Portland to Chicago O'Hare Intl Airport this week, the average price was $346, with the best Alaska Airlines deals starting from $217 round-trip. 11,413 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 $284 round-trip. Hawaiian Airlines operates 4 flights out of Portland into Chicago O'Hare Intl Airport in an average week, so prices vary by time and availability. 2,818 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
South Haven
Schaumburg
Rockford
Merrillville
Gurnee
Naperville
Rosemont
Kenosha
New Buffalo
Joliet
Oak Brook
Orland Park
Racine
Hammond
Tinley Park
Janesville
Aurora
Elgin
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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