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Cheap flights from Portland to Chicago from $113

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 2/9. 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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Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
12:47 pm - 12:12 amPDX-ORD
9h 25m1 stop
Multiple Airlines Logo
7:44 pm - 3:00 pmORD-PDX
21h 16m2 stops
$239Multiple Airlines
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Thu, Dec 25 - Tue, Dec 30
Frontier Logo
12:47 pm - 12:12 amPDX-ORD
9h 25m1 stop
Frontier Logo
10:01 pm - 10:34 amORD-PDX
14h 33m1 stop
$240Frontier
Find Deal
Sun, Dec 21 - Sun, Jan 11
Alaska Airlines Logo
5:30 pm - 5:04 amPDX-ORD
9h 34m1 stop
Alaska Airlines Logo
7:45 am - 12:36 pmORD-PDX
6h 51m1 stop
$242Alaska Airlines
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Sat, Mar 7 - Sat, Mar 14
United Airlines Logo
11:59 pm - 5:52 amPDX-ORD
3h 53mnonstop
United Airlines Logo
9:05 am - 11:48 amORD-PDX
4h 43mnonstop
$243United Airlines
Find Deal
Mon, Nov 24 - Thu, Nov 27
Alaska Airlines Logo
5:49 pm - 2:39 pmPDX-ORD
18h 50m1 stop
Alaska Airlines Logo
2:12 pm - 4:50 pmORD-PDX
4h 38mnonstop
$245Alaska Airlines
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Fri, Dec 5 - Thu, Dec 18
Delta Logo
2:23 pm - 11:59 pmPDX-ORD
7h 36m1 stop
Delta Logo
2:30 pm - 12:15 amORD-PDX
11h 45m2 stops
$250Delta
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Wed, Dec 3 - Tue, Dec 9
Delta Logo
11:20 pm - 8:04 amPDX-ORD
6h 44m1 stop
Delta Logo
2:14 pm - 6:50 pmORD-PDX
6h 36m1 stop
$251Delta
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Wed, Dec 3 - Thu, Dec 11
American Airlines Logo
11:37 am - 5:52 pmPDX-ORD
4h 15mnonstop
American Airlines Logo
9:57 am - 12:38 pmORD-PDX
4h 41mnonstop
$252American Airlines
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Wed, Dec 10 - Mon, Dec 15
United Airlines Logo
11:59 pm - 5:52 amPDX-ORD
3h 53mnonstop
United Airlines Logo
2:06 pm - 8:29 pmORD-PDX
8h 23m1 stop
$253United Airlines
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Mon, Nov 24 - Thu, Nov 27
American Airlines Logo
11:37 am - 5:52 pmPDX-ORD
4h 15mnonstop
American Airlines Logo
9:57 am - 12:38 pmORD-PDX
4h 41mnonstop
$269American Airlines
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Wed, Dec 3 - Sun, Dec 14

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
Dec 21
PDX12:47 pmPortland
9h 25m
1 stop
ORD12:12 amChicago O'Hare Intl
Jan 11
ORD10:01 pmChicago O'Hare Intl
14h 33m
1 stop
PDX10:34 amPortland
$240
Find similar
Frontier
Nov 10
PDX3:26 pmPortland
6h 49m
1 stop
ORD12:15 amChicago O'Hare Intl
Nov 13
ORD6:00 amChicago O'Hare Intl
7h 56m
1 stop
PDX11:56 amPortland
$252
Find similar
Frontier
Nov 17
PDX3:26 pmPortland
6h 49m
1 stop
ORD12:15 amChicago O'Hare Intl
Nov 23
ORD9:38 pmChicago O'Hare Intl
12h 26m
1 stop
PDX8:04 amPortland
$253
Find similar

Delta flights from Portland to Chicago O'Hare Intl Airport

Our best Delta deals on Portland to Chicago O'Hare Intl Airport flight tickets
Delta
Dec 3
PDX2:23 pmPortland
7h 36m
1 stop
ORD11:59 pmChicago O'Hare Intl
Dec 9
ORD2:30 pmChicago O'Hare Intl
11h 45m
2 stops
PDX12:15 amPortland
$250
Find similar
Delta
Dec 3
PDX11:20 pmPortland
6h 44m
1 stop
ORD8:04 amChicago O'Hare Intl
Dec 11
ORD2:14 pmChicago O'Hare Intl
6h 36m
1 stop
PDX6:50 pmPortland
$251
Find similar
Delta
Dec 7
PDX11:20 pmPortland
8h 40m
1 stop
ORD10:00 amChicago O'Hare Intl
Dec 11
ORD2:14 pmChicago O'Hare Intl
6h 36m
1 stop
PDX6:50 pmPortland
$255
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 November 6, 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 12/25

12:47 pm-12:12 am

1 stop9h 25m

Chicago O'Hare Intl

Tue 12/30

7:44 pm-3:00 pm

2 stops21h 16m

$239

PortlandChicago

PDX - ORD

PDXORD

Portland

Sun 12/21

12:47 pm-12:12 am

1 stop9h 25m

Chicago O'Hare Intl

Sun 1/11

10:01 pm-10:34 am

1 stop14h 33m

$240

PortlandChicago

PDX - ORD

PDXORD

Portland

Sat 3/7

5:30 pm-5:04 am

1 stop9h 34m

Chicago O'Hare Intl

Sat 3/14

7:45 am-12:36 pm

1 stop6h 51m

$242

PortlandChicago

PDX - ORD

PDXORD

Portland

Mon 11/24

11:59 pm-5:52 am

Nonstop3h 53m

Chicago O'Hare Intl

Thu 11/27

9:05 am-11:48 am

Nonstop4h 43m

$243

PortlandChicago

PDX - ORD

PDXORD

Portland

Fri 12/5

5:49 pm-2:39 pm

1 stop18h 50m

Chicago O'Hare Intl

Thu 12/18

2:12 pm-4:50 pm

Nonstop4h 38m

$245

PortlandChicago

PDX - ORD

PDXORD

Portland

Wed 12/3

2:23 pm-11:59 pm

1 stop7h 36m

Chicago O'Hare Intl

Tue 12/9

2:30 pm-12:15 am

2 stops11h 45m

$250

PortlandChicago

PDX - ORD

PDXORD

Portland

Wed 12/3

11:20 pm-8:04 am

1 stop6h 44m

Chicago O'Hare Intl

Thu 12/11

2:14 pm-6:50 pm

1 stop6h 36m

$251

PortlandChicago

PDX - ORD

PDXORD

Portland

Wed 12/10

11:37 am-5:52 pm

Nonstop4h 15m

Chicago O'Hare Intl

Mon 12/15

9:57 am-12:38 pm

Nonstop4h 41m

$252

PortlandChicago

PDX - ORD

PDXORD

Portland

Mon 11/24

11:59 pm-5:52 am

Nonstop3h 53m

Chicago O'Hare Intl

Thu 11/27

2:06 pm-8:29 pm

1 stop8h 23m

$253

PortlandChicago

PDX - ORD

PDXORD

Portland

Wed 12/3

11:37 am-5:52 pm

Nonstop4h 15m

Chicago O'Hare Intl

Sun 12/14

9:57 am-12:38 pm

Nonstop4h 41m

$269

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 Friday when prices can be found for as low as $438. 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 $570.

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 $316 when looking at flights departing in the afternoon. Try not to purchase tickets in the morning because they tend to be around $513. 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 $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?

You could potentially save up to 12% 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 November 2025, prices for Portland to Chicago O'Hare Intl Airport flights are approximately 13% 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

$190

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 $190. The best round-trip flight deal from Portland to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $346.
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 3h 53m, 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 $94Free CancellationRating
5.8
3,116 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $119Free CancellationRating
6.3
8,115 reviews
Search Spirit Airlines flights
DeltaPriceFrom $123Free CancellationRating
7.9
8,001 reviews
Search Delta flights
Hawaiian AirlinesPriceFrom $125Free CancellationRating
7.8
2,804 reviews
Search Hawaiian Airlines flights
American AirlinesPriceFrom $192Free CancellationRating
7.2
11,040 reviews
Search American Airlines flights
Alaska AirlinesPriceFrom $216Free CancellationRating
8.0
11,243 reviews
Search Alaska Airlines flights
United AirlinesPriceFrom $222Free CancellationRating
7.4
9,003 reviews
Search United Airlines flights

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

    Across 12 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 $216 round-trip. 11,243 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 13 flights out of Portland into Chicago O'Hare Intl Airport in an average week, so prices vary by time and availability. 2,804 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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