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Cheap flights from Portland to Chicago from $108

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 5/4. 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
7:46 pm - 4:53 pm
PDX
-
ORD
19h 07m
1 stop
Multiple Airlines Logo
7:21 pm - 11:57 am
ORD
-
PDX
18h 36m
1 stop
$216Multiple Airlines
Sun, Apr 19 - Sat, Apr 25
Alaska Airlines Logo
7:00 am - 1:11 pm
PDX
-
ORD
4h 11mnonstop
Alaska Airlines Logo
5:29 pm - 11:44 pm
ORD
-
PDX
8h 15m
1 stop
$217Alaska Airlines
Tue, Mar 3 - Mon, Mar 9
Frontier Logo
11:48 am - 9:50 am
PDX
-
ORD
20h 02m
1 stop
Frontier Logo
10:55 am - 1:02 pm
ORD
-
PDX
28h 07m
1 stop
$222Frontier
Thu, Apr 23 - Mon, Apr 27
American Airlines Logo
11:35 pm - 5:32 am
PDX
-
ORD
3h 57mnonstop
American Airlines Logo
8:25 am - 10:58 am
ORD
-
PDX
4h 33mnonstop
$224American Airlines
Sat, Feb 21 - Mon, Feb 23
Alaska Airlines Logo
9:26 pm - 2:58 pm
PDX
-
ORD
15h 32m
1 stop
Alaska Airlines Logo
2:07 pm - 4:50 pm
ORD
-
PDX
4h 43mnonstop
$225Alaska Airlines
Fri, Mar 13 - Tue, Mar 17
Alaska Airlines Logo
7:00 am - 1:11 pm
PDX
-
ORD
4h 11mnonstop
Alaska Airlines Logo
5:29 pm - 10:41 pm
ORD
-
PDX
7h 12m
1 stop
$227Alaska Airlines
Mon, Mar 2 - Tue, Mar 10
Frontier Logo
12:27 pm - 6:47 am
PDX
-
ORD
16h 20m
2 stops
Frontier Logo
7:21 pm - 11:57 am
ORD
-
PDX
18h 36m
1 stop
$230Frontier
Sat, Apr 18 - Sat, Apr 25
American Airlines Logo
11:59 pm - 5:56 am
PDX
-
ORD
3h 57mnonstop
American Airlines Logo
9:49 pm - 12:20 am
ORD
-
PDX
4h 31mnonstop
$231American Airlines
Thu, Mar 26 - Tue, Mar 31
Alaska Airlines Logo
7:00 am - 1:11 pm
PDX
-
ORD
4h 11mnonstop
Alaska Airlines Logo
2:07 pm - 4:50 pm
ORD
-
PDX
4h 43mnonstop
$232Alaska Airlines
Wed, Feb 25 - Mon, Mar 9
Frontier Logo
1:48 pm - 3:11 pm
PDX
-
ORD
23h 23m
2 stops
Frontier Logo
7:21 pm - 11:57 am
ORD
-
PDX
18h 36m
1 stop
$233Frontier
Tue, Apr 14 - Sat, Apr 18

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
Feb 21
PDX11:35 pmPortland
3h 57m
ORD5:32 amChicago O'Hare Intl
Feb 23
ORD8:25 amChicago O'Hare Intl
4h 33m
PDX10:58 amPortland
$224
American Airlines
Mar 26
PDX11:59 pmPortland
3h 57m
ORD5:56 amChicago O'Hare Intl
Mar 31
ORD9:49 pmChicago O'Hare Intl
4h 31m
PDX12:20 amPortland
$231
American Airlines
Apr 23
PDX3:16 pmPortland
4h 18m
ORD9:34 pmChicago O'Hare Intl
Apr 26
ORD9:22 pmChicago O'Hare Intl
4h 31m
PDX11:53 pmPortland
$242

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
Mar 3
PDX1:53 pmPortland
5h 37m
1 stop
ORD9:30 pmChicago O'Hare Intl
Mar 10
ORD1:57 pmChicago O'Hare Intl
9h 56m
1 stop
PDX9:53 pmPortland
$217
Delta
Feb 21
PDX3:59 pmPortland
5h 53m
1 stop
ORD11:52 pmChicago O'Hare Intl
Feb 24
ORD2:20 pmChicago O'Hare Intl
6h 28m
1 stop
PDX6:48 pmPortland
$234
Delta
Mar 2
PDX3:59 pmPortland
5h 53m
1 stop
ORD11:52 pmChicago O'Hare Intl
Mar 9
ORD1:19 pmChicago O'Hare Intl
6h 56m
1 stop
PDX6:15 pmPortland
$237

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 February 3, 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

PortlandChicago

PDX - ORD

PDXORD

Portland

Sun 4/19

7:46 pm-4:53 pm

1 stop19h 07m

Chicago O'Hare Intl

Sat 4/25

7:21 pm-11:57 am

1 stop18h 36m

$216

PortlandChicago

PDX - ORD

PDXORD

Portland

Tue 3/3

7:00 am-1:11 pm

Nonstop4h 11m

Chicago O'Hare Intl

Mon 3/9

5:29 pm-11:44 pm

1 stop8h 15m

$217

PortlandChicago

PDX - ORD

PDXORD

Portland

Thu 4/23

11:48 am-9:50 am

1 stop20h 02m

Chicago O'Hare Intl

Mon 4/27

10:55 am-1:02 pm

1 stop28h 07m

$222

PortlandChicago

PDX - ORD

PDXORD

Portland

Sat 2/21

11:35 pm-5:32 am

Nonstop3h 57m

Chicago O'Hare Intl

Mon 2/23

8:25 am-10:58 am

Nonstop4h 33m

$224

PortlandChicago

PDX - ORD

PDXORD

Portland

Fri 3/13

9:26 pm-2:58 pm

1 stop15h 32m

Chicago O'Hare Intl

Tue 3/17

2:07 pm-4:50 pm

Nonstop4h 43m

$225

PortlandChicago

PDX - ORD

PDXORD

Portland

Mon 3/2

7:00 am-1:11 pm

Nonstop4h 11m

Chicago O'Hare Intl

Tue 3/10

5:29 pm-10:41 pm

1 stop7h 12m

$227

PortlandChicago

PDX - ORD

PDXORD

Portland

Sat 4/18

12:27 pm-6:47 am

2 stops16h 20m

Chicago O'Hare Intl

Sat 4/25

7:21 pm-11:57 am

1 stop18h 36m

$230

PortlandChicago

PDX - ORD

PDXORD

Portland

Thu 3/26

11:59 pm-5:56 am

Nonstop3h 57m

Chicago O'Hare Intl

Tue 3/31

9:49 pm-12:20 am

Nonstop4h 31m

$231

PortlandChicago

PDX - ORD

PDXORD

Portland

Wed 2/25

7:00 am-1:11 pm

Nonstop4h 11m

Chicago O'Hare Intl

Mon 3/9

2:07 pm-4:50 pm

Nonstop4h 43m

$232

PortlandChicago

PDX - ORD

PDXORD

Portland

Tue 4/14

1:48 pm-3:11 pm

2 stops23h 23m

Chicago O'Hare Intl

Sat 4/18

7:21 pm-11:57 am

1 stop18h 36m

$233

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 February is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Portland averaging around $297.

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 $430. 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 $552.

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 $314 when looking at flights departing in the afternoon. Try not to purchase tickets in the morning because they tend to be around $494. 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 $347 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 $303 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 1% 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 February 2026, prices for Portland to Chicago O'Hare Intl Airport flights are approximately 21% 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

$166

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 $166. The best round-trip flight deal from Portland to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $318.
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
FrontierPriceFrom $86Free CancellationRating
5.7
3,051 reviews
Search Frontier flights
DeltaPriceFrom $99Free CancellationRating
7.9
8,139 reviews
Search Delta flights
Spirit AirlinesPriceFrom $119Free CancellationRating
6.3
8,409 reviews
Search Spirit Airlines flights
Hawaiian AirlinesPriceFrom $125Free CancellationRating
7.8
2,831 reviews
Search Hawaiian Airlines flights
American AirlinesPriceFrom $196Free CancellationRating
7.2
11,218 reviews
Search American Airlines flights
United AirlinesPriceFrom $205Free CancellationRating
7.4
9,236 reviews
Search United Airlines flights
Alaska AirlinesPriceFrom $215Free CancellationRating
8.0
11,835 reviews
Search Alaska 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 $349, with the best Alaska Airlines deals starting from $215 round-trip. 11,835 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 $283 round-trip. Hawaiian Airlines operates 5 flights out of Portland into Chicago O'Hare Intl Airport in an average week, so prices vary by time and availability. 2,831 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
Naperville
Rosemont
New Buffalo
Kenosha
Joliet
Oak Brook
Orland Park
Racine
Hammond
Janesville
Tinley Park
Elgin
Aurora
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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