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Cheap flights from Portland to Chicago from $110

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 10/16. 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

Frontier Logo
6:05 am - 11:39 pmPDX-ORD
15h 34m2 stops
Frontier Logo
7:15 am - 11:48 amORD-PDX
6h 33m1 stop
$195Frontier
Find Deal
Thu, Oct 2 - Tue, Oct 7
Multiple Airlines Logo
12:07 pm - 9:36 pmPDX-ORD
7h 29m1 stop
Multiple Airlines Logo
10:32 am - 11:48 amORD-PDX
27h 16m1 stop
$196Multiple Airlines
Find Deal
Thu, Oct 2 - Mon, Oct 6
American Airlines Logo
11:58 pm - 5:53 amPDX-ORD
3h 55mnonstop
American Airlines Logo
8:14 am - 10:48 amORD-PDX
4h 34mnonstop
$209American Airlines
Find Deal
Fri, Oct 31 - Wed, Nov 5
American Airlines Logo
11:58 pm - 5:53 amPDX-ORD
3h 55mnonstop
American Airlines Logo
10:00 am - 12:36 pmORD-PDX
4h 36mnonstop
$210American Airlines
Find Deal
Fri, Oct 31 - Sat, Nov 8
Hawaiian Airlines Logo
11:00 pm - 5:01 amPDX-ORD
4h 01mnonstop
Hawaiian Airlines Logo
2:54 pm - 11:33 pmORD-PDX
10h 39m1 stop
$211Hawaiian Airlines
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Fri, Oct 31 - Sat, Nov 8
United Airlines Logo
11:59 pm - 5:52 amPDX-ORD
3h 53mnonstop
United Airlines Logo
9:05 am - 11:48 amORD-PDX
4h 43mnonstop
$222United Airlines
Find Deal
Fri, Oct 31 - Sun, Nov 2
Alaska Airlines Logo
7:00 am - 1:09 pmPDX-ORD
4h 09mnonstop
Alaska Airlines Logo
7:00 am - 9:39 amORD-PDX
4h 39mnonstop
$228Alaska Airlines
Find Deal
Wed, Nov 5 - Mon, Nov 10
United Airlines Logo
11:59 pm - 6:00 amPDX-ORD
4h 01mnonstop
United Airlines Logo
7:50 pm - 10:25 pmORD-PDX
4h 35mnonstop
$231United Airlines
Find Deal
Sat, Oct 18 - Tue, Oct 21
Alaska Airlines Logo
11:00 pm - 5:01 amPDX-ORD
4h 01mnonstop
Alaska Airlines Logo
7:00 am - 9:32 amORD-PDX
4h 32mnonstop
$238Alaska Airlines
Find Deal
Fri, Oct 24 - Sat, Oct 25
Hawaiian Airlines Logo
7:00 am - 1:09 pmPDX-ORD
4h 09mnonstop
Hawaiian Airlines Logo
2:54 pm - 8:46 pmORD-PDX
7h 52m1 stop
$241Hawaiian Airlines
Find Deal
Tue, Oct 28 - Tue, Nov 4

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
Oct 31
PDX11:58 pmPortland
3h 55m
ORD5:53 amChicago O'Hare Intl
Nov 5
ORD8:14 amChicago O'Hare Intl
4h 34m
PDX10:48 amPortland
$209
Find similar
American Airlines
Oct 31
PDX11:58 pmPortland
3h 55m
ORD5:53 amChicago O'Hare Intl
Nov 8
ORD10:00 amChicago O'Hare Intl
4h 36m
PDX12:36 pmPortland
$210
Find similar
American Airlines
Sep 30
PDX6:07 amPortland
4h 05m
ORD12:12 pmChicago O'Hare Intl
Oct 7
ORD7:09 amChicago O'Hare Intl
4h 22m
PDX9:31 amPortland
$335
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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
Oct 2
PDX6:05 amPortland
15h 34m
2 stops
ORD11:39 pmChicago O'Hare Intl
Oct 7
ORD7:15 amChicago O'Hare Intl
6h 33m
1 stop
PDX11:48 amPortland
$195
Find similar
Frontier
Oct 26
PDX12:43 pmPortland
18h 53m
1 stop
ORD9:36 amChicago O'Hare Intl
Oct 31
ORD6:00 amChicago O'Hare Intl
7h 56m
1 stop
PDX11:56 amPortland
$198
Find similar
Frontier
Oct 14
PDX12:43 pmPortland
9h 10m
1 stop
ORD11:53 pmChicago O'Hare Intl
Oct 21
ORD7:15 amChicago O'Hare Intl
6h 33m
1 stop
PDX11:48 amPortland
$199
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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 September 16, 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 10/2

6:05 am-11:39 pm

2 stops15h 34m

Chicago O'Hare Intl

Tue 10/7

7:15 am-11:48 am

1 stop6h 33m

$195

PortlandChicago

PDX - ORD

PDXORD

Portland

Thu 10/2

12:07 pm-9:36 pm

1 stop7h 29m

Chicago O'Hare Intl

Mon 10/6

10:32 am-11:48 am

1 stop27h 16m

$196

PortlandChicago

PDX - ORD

PDXORD

Portland

Fri 10/31

11:58 pm-5:53 am

Nonstop3h 55m

Chicago O'Hare Intl

Wed 11/5

8:14 am-10:48 am

Nonstop4h 34m

$209

PortlandChicago

PDX - ORD

PDXORD

Portland

Fri 10/31

11:58 pm-5:53 am

Nonstop3h 55m

Chicago O'Hare Intl

Sat 11/8

10:00 am-12:36 pm

Nonstop4h 36m

$210

PortlandChicago

PDX - ORD

PDXORD

Portland

Fri 10/31

11:00 pm-5:01 am

Nonstop4h 01m

Chicago O'Hare Intl

Sat 11/8

2:54 pm-11:33 pm

1 stop10h 39m

$211

PortlandChicago

PDX - ORD

PDXORD

Portland

Fri 10/31

11:59 pm-5:52 am

Nonstop3h 53m

Chicago O'Hare Intl

Sun 11/2

9:05 am-11:48 am

Nonstop4h 43m

$222

PortlandChicago

PDX - ORD

PDXORD

Portland

Wed 11/5

7:00 am-1:09 pm

Nonstop4h 09m

Chicago O'Hare Intl

Mon 11/10

7:00 am-9:39 am

Nonstop4h 39m

$228

PortlandChicago

PDX - ORD

PDXORD

Portland

Sat 10/18

11:59 pm-6:00 am

Nonstop4h 01m

Chicago O'Hare Intl

Tue 10/21

7:50 pm-10:25 pm

Nonstop4h 35m

$231

PortlandChicago

PDX - ORD

PDXORD

Portland

Fri 10/24

11:00 pm-5:01 am

Nonstop4h 01m

Chicago O'Hare Intl

Sat 10/25

7:00 am-9:32 am

Nonstop4h 32m

$238

PortlandChicago

PDX - ORD

PDXORD

Portland

Tue 10/28

7:00 am-1:09 pm

Nonstop4h 09m

Chicago O'Hare Intl

Tue 11/4

2:54 pm-8:46 pm

1 stop7h 52m

$241

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 $298.

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 $453. 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 $576.

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 $312 when looking at flights departing in the afternoon. Try not to purchase tickets in the morning because they tend to be around $523. 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 $360 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.

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

As of September 2025, prices for Portland to Chicago O'Hare Intl Airport flights are approximately 4% 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

$169

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 $169. The best round-trip flight deal from Portland to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $324.
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 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
Spirit AirlinesPriceFrom $93Free CancellationRating
6.3
8,019 reviews
Search Spirit Airlines flights
FrontierPriceFrom $108Free CancellationRating
5.8
3,174 reviews
Search Frontier flights
DeltaPriceFrom $123Free CancellationRating
7.9
7,957 reviews
Search Delta flights
Hawaiian AirlinesPriceFrom $125Free CancellationRating
7.8
2,724 reviews
Search Hawaiian Airlines flights
American AirlinesPriceFrom $195Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
Alaska AirlinesPriceFrom $200Free CancellationRating
8.0
10,000 reviews
Search Alaska Airlines flights
United AirlinesPriceFrom $226Free CancellationRating
7.4
8,924 reviews
Search United Airlines flights

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

    Across 3 Alaska Airlines flights from Portland to Chicago O'Hare Intl Airport this week, the average price was $348, with the best Alaska Airlines deals starting from $200 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 3 flights out of Portland into Chicago O'Hare Intl Airport in an average week, so prices vary by time and availability. 2,724 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
Rockford
Schaumburg
Merrillville
Gurnee
Naperville
Rosemont
Kenosha
New Buffalo
Joliet
Oak Brook
Racine
Hammond
Orland Park
Tinley 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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