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Cheap flights from Portland to Chicago O'Hare Intl Airport from $55

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 O'Hare Intl Airport departing on 3/1. 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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Find the cheapest flights from Portland to Chicago

Cheap round-trip flights

These are some of the best round-trip flight deals from Portland to Chicago that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Portland to Chicago.

Cheap last minute flights

Planning a quick getaway from Portland to Chicago? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Chicago, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Portland to Chicago

Find recent round-trip train or bus tickets from Portland to Chicago.

All round-trip flight deals from Portland to Chicago

The cheapest plane tickets from Portland to Chicago found on KAYAK recently.
6:32 am - 5:25 pmPDX-ORD
8h 53m1 stop
7:59 pm - 8:40 amORD-PDX
14h 41m1 stop
$110Frontier
Find Deal
Sat, Mar 1 - Sat, Mar 1
6:32 am - 12:23 amPDX-ORD
15h 51m1 stop
6:45 am - 12:37 amORD-PDX
19h 52m1 stop
$119Frontier
Find Deal
Thu, Mar 6 - Thu, Mar 13
8:28 pm - 6:07 amPDX-ORD
7h 39m1 stop
10:45 pm - 9:21 amORD-PDX
12h 36m1 stop
$158Spirit Airlines
Find Deal
Tue, Feb 18 - Wed, Feb 19
8:28 pm - 6:07 amPDX-ORD
7h 39m1 stop
7:41 am - 1:38 pmORD-PDX
7h 57m1 stop
$168Spirit Airlines
Find Deal
Wed, Feb 26 - Wed, Mar 5
7:00 am - 1:07 pmPDX-ORD
4h 07mnonstop
7:00 pm - 9:58 amORD-PDX
16h 58m1 stop
$232Alaska Airlines
Find Deal
Mon, Feb 10 - Wed, Feb 19
7:00 am - 1:04 pmPDX-ORD
4h 04mnonstop
5:54 pm - 10:56 pmORD-PDX
7h 02m1 stop
$237Alaska Airlines
Find Deal
Wed, Feb 19 - Tue, Feb 25
11:55 pm - 6:00 amPDX-ORD
4h 05mnonstop
8:25 pm - 11:01 pmORD-PDX
4h 36mnonstop
$249American Airlines
Find Deal
Sun, Apr 27 - Fri, May 2
11:58 pm - 5:55 amPDX-ORD
3h 57mnonstop
9:11 am - 11:54 amORD-PDX
4h 43mnonstop
$261United Airlines
Find Deal
Thu, Mar 6 - Wed, Mar 12
11:58 pm - 5:55 amPDX-ORD
3h 57mnonstop
7:59 pm - 10:39 pmORD-PDX
4h 40mnonstop
$272United Airlines
Find Deal
Thu, Mar 6 - Mon, Mar 17
3:00 pm - 9:07 pmPDX-ORD
4h 07mnonstop
5:00 am - 10:55 amORD-PDX
7h 55m1 stop
$292American Airlines
Find Deal
Wed, Apr 23 - Tue, Apr 29
6:32 am - 5:25 pmPDX-ORD
8h 53m1 stop
$55Frontier
Find Deal
Sat, Mar 1
5:16 pm - 11:45 pmPDX-ORD
28h 29m1 stop
$56Frontier
Find Deal
Thu, May 1
8:28 pm - 6:07 amPDX-ORD
7h 39m1 stop
$74Spirit Airlines
Find Deal
Mon, Feb 24
8:28 pm - 6:07 amPDX-ORD
7h 39m1 stop
$78Spirit Airlines
Find Deal
Tue, Feb 18
7:00 am - 1:04 pmPDX-ORD
4h 04mnonstop
$114Alaska Airlines
Find Deal
Sat, Feb 22
7:05 am - 1:05 pmPDX-ORD
4h 00mnonstop
$125United Airlines
Find Deal
Fri, Feb 21
7:00 am - 1:04 pmPDX-ORD
4h 04mnonstop
$134Alaska Airlines
Find Deal
Wed, Mar 12
11:58 pm - 5:55 amPDX-ORD
3h 57mnonstop
$148United Airlines
Find Deal
Thu, Mar 6
11:55 pm - 6:00 amPDX-ORD
4h 05mnonstop
$169American Airlines
Find Deal
Thu, May 1
11:59 pm - 9:55 amPDX-ORD
7h 56m1 stop
$179American Airlines
Find Deal
Fri, Jun 20
12:03 pm - 12:32 amPDX-ORD
10h 29m1 stop
10:47 pm - 9:21 amORD-PDX
12h 34m1 stop
Sun, Jan 26 - Thu, Jan 30
5:30 pm - 5:31 amPDX-ORD
10h 01m1 stop
10:47 pm - 9:21 amORD-PDX
12h 34m1 stop
$232Spirit Airlines
Find Deal
Fri, Jan 24 - Thu, Jan 30
7:00 am - 1:07 pmPDX-ORD
4h 07mnonstop
4:05 pm - 6:44 pmORD-PDX
4h 39mnonstop
$478Alaska Airlines
Find Deal
Thu, Jan 23 - Sat, Feb 15
12:45 am - 11:20 amPDX-ORD
8h 35m1 stop
2:55 pm - 9:53 pmORD-PDX
8h 58m1 stop
$513Delta
Find Deal
Sun, Jan 26 - Mon, Feb 3
12:45 am - 8:59 amPDX-ORD
6h 14m1 stop
4:15 pm - 8:35 pmORD-PDX
6h 20m1 stop
$587Delta
Find Deal
Sun, Jan 26 - Mon, Jan 27
10:56 am - 4:57 pmPDX-ORD
4h 01mnonstop
4:15 pm - 6:48 pmORD-PDX
4h 33mnonstop
$589United Airlines
Find Deal
Thu, Jan 23 - Sat, Feb 15
7:00 am - 1:07 pmPDX-ORD
4h 07mnonstop
3:35 pm - 6:18 pmORD-PDX
4h 43mnonstop
$637Alaska Airlines
Find Deal
Thu, Jan 23 - Mon, Jan 27
6:45 am - 7:40 pmPDX-ORD
10h 55m1 stop
6:15 am - 1:55 pmORD-PDX
9h 40m2 stops
$662Southwest
Find Deal
Sat, Jan 25 - Wed, Jan 29
5:20 am - 6:10 pmPDX-ORD
10h 50m2 stops
5:45 am - 3:10 pmORD-PDX
11h 25m2 stops
$667Southwest
Find Deal
Sat, Jan 25 - Wed, Jan 29
7:00 am - 1:01 pmPDX-ORD
4h 01mnonstop
7:10 am - 6:05 pmORD-PDX
12h 55m1 stop
$700United Airlines
Find Deal
Wed, Jan 22 - Sat, Feb 1
2:02 pm - 8:08 pmPDX-ORD
4h 06mnonstop
4:13 pm - 6:45 pmORD-PDX
4h 32mnonstop
$227United Airlines
Find Deal
Tue, Apr 29 - Sat, May 3
7:00 am - 1:04 pmPDX-ORD
4h 04mnonstop
4:05 pm - 6:44 pmORD-PDX
4h 39mnonstop
$238Alaska Airlines
Find Deal
Fri, Feb 21 - Tue, Feb 25
7:00 am - 1:04 pmPDX-ORD
4h 04mnonstop
4:05 pm - 6:44 pmORD-PDX
4h 39mnonstop
$241Alaska Airlines
Find Deal
Sat, Mar 1 - Sat, Mar 1
7:00 am - 1:04 pmPDX-ORD
4h 04mnonstop
4:05 pm - 6:44 pmORD-PDX
4h 39mnonstop
$247Alaska Airlines
Find Deal
Wed, Feb 19 - Sat, Mar 1
7:00 am - 1:04 pmPDX-ORD
4h 04mnonstop
4:05 pm - 6:44 pmORD-PDX
4h 39mnonstop
$248Alaska Airlines
Find Deal
Tue, Feb 18 - Tue, Feb 25
11:55 pm - 6:00 amPDX-ORD
4h 05mnonstop
8:25 pm - 11:01 pmORD-PDX
4h 36mnonstop
$249American Airlines
Find Deal
Sun, Apr 27 - Fri, May 2
11:58 pm - 5:55 amPDX-ORD
3h 57mnonstop
9:11 am - 11:54 amORD-PDX
4h 43mnonstop
$261United Airlines
Find Deal
Thu, Mar 6 - Wed, Mar 12
11:58 pm - 5:55 amPDX-ORD
3h 57mnonstop
7:59 pm - 10:39 pmORD-PDX
4h 40mnonstop
$272United Airlines
Find Deal
Thu, Mar 6 - Mon, Mar 17
11:41 pm - 5:36 amPDX-ORD
3h 55mnonstop
7:10 am - 9:34 amORD-PDX
4h 24mnonstop
$282American Airlines
Find Deal
Sat, Jul 19 - Tue, Jul 22
3:00 pm - 9:07 pmPDX-ORD
4h 07mnonstop
10:05 am - 12:32 pmORD-PDX
4h 27mnonstop
$293American Airlines
Find Deal
Fri, Apr 25 - Sun, Apr 27

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
Mar 6
PDX11:58 pmPortland
3h 57m
ORD5:55 amChicago O'Hare Intl
Mar 12
ORD9:11 amChicago O'Hare Intl
4h 43m
PDX11:54 amPortland
United Airlines
Mar 6
PDX11:58 pmPortland
3h 57m
ORD5:55 amChicago O'Hare Intl
Mar 17
ORD7:59 pmChicago O'Hare Intl
4h 40m
PDX10:39 pmPortland
United Airlines
Feb 10
PDX11:59 pmPortland
4h 01m
ORD6:00 amChicago O'Hare Intl
Feb 22
ORD9:11 amChicago O'Hare Intl
4h 43m
PDX11:54 amPortland

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
Feb 18
PDX8:28 pmPortland
7h 39m
1 stop
ORD6:07 amChicago O'Hare Intl
Feb 19
ORD10:45 pmChicago O'Hare Intl
12h 36m
1 stop
PDX9:21 amPortland
Spirit Airlines
Feb 26
PDX8:28 pmPortland
7h 39m
1 stop
ORD6:07 amChicago O'Hare Intl
Mar 5
ORD7:41 amChicago O'Hare Intl
7h 57m
1 stop
PDX1:38 pmPortland
Spirit Airlines
Feb 26
PDX8:28 pmPortland
7h 39m
1 stop
ORD6:07 amChicago O'Hare Intl
Mar 4
ORD1:32 pmChicago O'Hare Intl
7h 59m
1 stop
PDX7:31 pmPortland

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 $307.

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 Thursday when prices can be found for as low as $488. 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 $635.

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 evening is the least expensive time of day to depart. momondo users have found prices as low as $277 when looking at flights departing in the evening. Try not to purchase tickets in the morning because they tend to be around $400. 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 6 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 6 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 $290 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 January 2025, prices for Portland to Chicago O'Hare Intl Airport flights are approximately 44% 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

$55

Fastest flight time

3h 57m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Portland in the past 72 hours is $55. The best round-trip flight deal from Portland to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $110.
The fastest flight from Portland to Chicago O'Hare Intl Airport takes 3h 57m
Direct flights go from Portland to Chicago O'Hare Intl Airport every day.

  • 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 57m, 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 $82Free CancellationRating
6.3
8,116 reviews
Search Spirit Airlines flights
FrontierPriceFrom $108Free CancellationRating
6.0
3,443 reviews
Search Frontier flights
Alaska AirlinesPriceFrom $178Free CancellationRating
8.0
9,706 reviews
Search Alaska Airlines flights
American AirlinesPriceFrom $188Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
DeltaPriceFrom $207Free CancellationRating
8.0
8,521 reviews
Search Delta flights
United AirlinesPriceFrom $217Free CancellationRating
7.4
8,984 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 $343, with the best Alaska Airlines deals starting from $178 round-trip. 9,706 users have rated Alaska Airlines on momondo, with an average score of 8.0/10.

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

    The best United Airlines deal for Portland to Chicago O'Hare Intl Airport flight tickets found on momondo in the last 72 hours was $217, round-trip. It should be noted that an average United Airlines flight deal for this route in this time was higher, at $412 round-trip. United Airlines operates 22 flights out of Portland into Chicago O'Hare Intl Airport in an average week, so prices vary by time and availability. 8,984 United Airlines reviews by users on momondo have scored the airline at 7.4/10.


Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Rockford
Lake Geneva
Schaumburg
Merrillville
Rosemont
Gurnee
Naperville
Kenosha
Joliet
South Haven
Racine
Hammond
Oak Brook
South Holland
Tinley Park
New Buffalo
Elk Grove Village
Aurora
Elgin
Waukegan

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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