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Cheap flights from Portland to Chicago from $77

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 4/28. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Portland to Chicago

Cheap round-trip flights

KAYAK's recommended round-trip deals from the most popular airlines that fly from Portland to Chicago.
5:40 pm - 10:55 amPDX-ORD
15h 15m1 stop
9:02 pm - 4:45 pmORD-PDX
21h 43m1 stop
$159Spirit Airlines
Find Deal
Wed, May 7 - Tue, May 13
7:01 pm - 6:33 amPDX-ORD
9h 32m1 stop
7:12 pm - 9:12 amORD-PDX
16h 00m1 stop
$176Spirit Airlines
Find Deal
Wed, Apr 16 - Sun, Apr 20
11:59 pm - 6:00 amPDX-ORD
4h 01mnonstop
7:10 am - 9:42 amORD-PDX
4h 32mnonstop
$179United Airlines
Find Deal
Sat, May 24 - Sat, May 31
5:51 pm - 11:56 pmPDX-ORD
4h 05mnonstop
7:00 am - 9:25 amORD-PDX
4h 25mnonstop
$203Alaska Airlines
Find Deal
Thu, May 29 - Tue, Jun 17
10:59 pm - 5:00 amPDX-ORD
4h 01mnonstop
7:10 am - 9:42 amORD-PDX
4h 32mnonstop
$214United Airlines
Find Deal
Thu, May 29 - Mon, Jun 2
2:30 pm - 10:23 pmPDX-ORD
5h 53m1 stop
7:00 am - 9:23 amORD-PDX
4h 23mnonstop
$224Alaska Airlines
Find Deal
Sat, May 24 - Sat, May 31
6:20 am - 11:41 pmPDX-ORD
15h 21m1 stop
8:14 pm - 3:42 pmORD-PDX
21h 28m1 stop
$241Frontier
Find Deal
Fri, May 2 - Sun, May 4
11:52 pm - 5:57 amPDX-ORD
4h 05mnonstop
8:20 pm - 11:02 pmORD-PDX
4h 42mnonstop
$242American Airlines
Find Deal
Fri, Apr 25 - Sat, Apr 26
9:51 pm - 11:23 amPDX-MDW
11h 32m1 stop
8:03 pm - 12:38 amMDW-PDX
6h 35m1 stop
$278Frontier
Find Deal
Fri, May 2 - Sun, May 4
11:54 pm - 5:50 amPDX-ORD
3h 56mnonstop
8:25 pm - 11:04 pmORD-PDX
4h 39mnonstop
$294American Airlines
Find Deal
Thu, Jul 31 - Mon, Aug 4

United Airlines flights from Portland to Chicago

Our best United Airlines deals on Portland to Chicago flight tickets
United Airlines
May 24
PDX11:59 pmPortland
4h 01m
ORD6:00 amChicago O'Hare Intl
May 31
ORD7:10 amChicago O'Hare Intl
4h 32m
PDX9:42 amPortland
United Airlines
May 29
PDX10:59 pmPortland
4h 01m
ORD5:00 amChicago O'Hare Intl
Jun 2
ORD7:10 amChicago O'Hare Intl
4h 32m
PDX9:42 amPortland
United Airlines
Apr 26
PDX11:59 pmPortland
3h 57m
ORD5:56 amChicago O'Hare Intl
Apr 29
ORD9:17 amChicago O'Hare Intl
4h 35m
PDX11:52 amPortland

Alaska Airlines flights from Portland to Chicago

Our best Alaska Airlines deals on Portland to Chicago flight tickets
Alaska Airlines
May 29
PDX5:51 pmPortland
4h 05m
ORD11:56 pmChicago O'Hare Intl
Jun 17
ORD7:00 amChicago O'Hare Intl
4h 25m
PDX9:25 amPortland
Alaska Airlines
May 24
PDX2:30 pmPortland
5h 53m
1 stop
ORD10:23 pmChicago O'Hare Intl
May 31
ORD7:00 amChicago O'Hare Intl
4h 23m
PDX9:23 amPortland
Alaska Airlines
May 28
PDX5:51 pmPortland
4h 05m
ORD11:56 pmChicago O'Hare Intl
Jun 16
ORD7:00 amChicago O'Hare Intl
4h 25m
PDX9:25 amPortland

See travel insights to Chicago from

How to get the cheapest flight ticket from Portland to Chicago

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?

What is the cheapest month to fly to Chicago?

The month of January is, on average, the cheapest month to fly to Chicago from Portland, with most prices found around $263. If you’re not able to fly to Chicago in January, then August is your next best option. Flight prices from Portland to Chicago during August average around $297.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as $470. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Portland to Chicago for around $619.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the afternoon. Flights from Portland to Chicago during this time can be as low as $366. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $561.

What is the cheapest Portland to Chicago flight route?

Fly from Portland to Chicago Midway for the best Portland - Chicago flight prices

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from Portland when booking 11 weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $358 when searching 11 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Portland for as low as $292 on momondo.

What cabin class options are available on Portland to Chicago flights?

There are 4 cabin classes available to choose from on Portland to Chicago 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 flight prices changed over time?

As of March 2025, prices for Portland to Chicago flights are approximately 12% more expensive when compared to flights at the same time last year.

When to book flights from Portland to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Portland to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Portland to Chicago (PDX to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Portland to Chicago

Best Price Found

$77

Fastest flight time

3h 55m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from Portland in the past 72 hours is $77. The best round-trip flight deal from Portland to Chicago found on momondo in the last 72 hours is $159.
The fastest flight from Portland to Chicago takes 3h 55m
Direct flights go from Portland to Chicago every day.
There are 3 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW), Chicago Greater Rockford (RFD)

  • How far is Portland to Chicago by plane?

    Portland and Chicago are 1753.4 mi apart from one another. A reasonable flight in good conditions will take 3h 55m.

  • When did momondo last update prices for flights from Portland Airport to Chicago?

    Prices for flights from Portland Airport to Chicago are refreshed on a daily basis.

  • How many operators does momondo search for flights from Portland Airport to Chicago?

  • How old do you have to be to fly from Portland Airport to Chicago?

    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.

  • What documentation or ID do you need to fly to Chicago?

    The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Portland to Chicago?

  • What is the most popular airline from Portland to Chicago?


Best airlines flying from Portland to Chicago

Compare and see reviews for airlines that fly from Portland to Chicago with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $82Free CancellationRating
6.3
7,882 reviews
Search Spirit Airlines flights
FrontierPriceFrom $108Free CancellationRating
6.0
3,271 reviews
Search Frontier flights
Alaska AirlinesPriceFrom $185Free CancellationRating
8.0
9,798 reviews
Search Alaska Airlines flights
American AirlinesPriceFrom $189Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
Hawaiian AirlinesPriceFrom $202Free CancellationRating
7.9
2,336 reviews
Search Hawaiian Airlines flights
DeltaPriceFrom $207Free CancellationRating
8.0
7,895 reviews
Search Delta flights
United AirlinesPriceFrom $215Free CancellationRating
7.4
8,603 reviews
Search United Airlines flights
SouthwestPriceFrom $249Free CancellationRating
8.0
4,274 reviews
Search Southwest flights
  • Alaska Airlines Flights From Portland to Chicago

    Alaska Airlines flies from Portland to Chicago around 4 times per week, with 9,798 momondo users rating the airline 8.0/10. The cheapest Alaska Airlines deal from Portland to Chicago in the last 72 hours was $185 (round-trip), much lower than the average airfare cost of $340 for Alaska Airlines flights on this route.

  • Southwest Flights From Portland to Chicago

    Another popular option for Portland to Chicago flights is Southwest (8.0/10, 4,274 ratings). Southwest flies from Portland to Chicago around 5 times per week, with deals starting from $249 round-trip and rising to an average price of around $414.


Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Schererville
Crown Point
Munster
Monticello
Chesterton
Porter
Griffith
Saint John

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?

Flights from Portland to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Portland to Chicago?

Once all potential Portland to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Portland to Chicago right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Portland to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.


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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago