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Cheap flights from Portland to Chicago from $109

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 12/25. 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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Find the cheapest flights from Portland to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Alaska Airlines Logo
6:00 am - 2:11 pm
PDX
-
ORD
6h 11m1 stop
Alaska Airlines Logo
5:29 pm - 11:44 pm
ORD
-
PDX
8h 15m1 stop
$236Alaska Airlines
Sat, Feb 14 - Tue, Feb 17
Delta Logo
1:30 pm - 11:53 pm
PDX
-
ORD
8h 23m1 stop
Delta Logo
8:50 am - 12:46 pm
ORD
-
PDX
5h 56m1 stop
$237Delta
Wed, Jan 7 - Wed, Jan 14
Southwest Logo
6:30 am - 12:25 pm
PDX
-
MDW
3h 55mnonstop
Southwest Logo
4:10 pm - 10:30 pm
MDW
-
PDX
8h 20m1 stop
$237Southwest
Thu, Jan 8 - Tue, Jan 13
United Airlines Logo
1:24 pm - 9:15 pm
PDX
-
ORD
5h 51m1 stop
United Airlines Logo
5:16 pm - 11:06 pm
ORD
-
PDX
7h 50m1 stop
$242United Airlines
Wed, Jan 28 - Fri, Jan 30
Southwest Logo
6:30 am - 12:25 pm
PDX
-
MDW
3h 55mnonstop
Southwest Logo
8:10 am - 3:40 pm
MDW
-
PDX
9h 30m2 stops
$242Southwest
Tue, Jan 6 - Thu, Jan 8
United Airlines Logo
1:24 pm - 9:15 pm
PDX
-
ORD
5h 51m1 stop
United Airlines Logo
4:15 pm - 6:56 pm
ORD
-
PDX
4h 41mnonstop
$243United Airlines
Thu, Jan 8 - Mon, Jan 12
Frontier Logo
12:04 pm - 1:07 am
PDX
-
ORD
11h 03m1 stop
Frontier Logo
10:53 am - 11:09 am
ORD
-
PDX
26h 16m1 stop
$244Frontier
Fri, Mar 6 - Sun, Mar 8
Multiple Airlines Logo
11:59 am - 9:24 pm
PDX
-
ORD
7h 25m1 stop
Multiple Airlines Logo
8:00 am - 10:46 pm
ORD
-
PDX
16h 46m1 stop
$249Multiple Airlines
Thu, Jan 15 - Mon, Jan 19
Frontier Logo
12:05 pm - 2:05 pm
PDX
-
MDW
24h 00m1 stop
Frontier Logo
11:05 am - 10:33 am
MDW
-
PDX
25h 28m2 stops
$255Frontier
Thu, Jan 8 - Thu, Jan 15
Multiple Airlines Logo
2:29 pm - 7:45 pm
PDX
-
RFD
27h 16m2 stops
Multiple Airlines Logo
12:15 pm - 1:24 pm
RFD
-
PDX
27h 09m1 stop
$589Multiple Airlines
Thu, Dec 25 - Sat, Jan 3

Frontier flights from Portland to Chicago

Our best Frontier deals on Portland to Chicago flight tickets
Frontier
Mar 6
PDX12:04 pmPortland
11h 03m
1 stop
ORD1:07 amChicago O'Hare Intl
Mar 8
ORD10:53 amChicago O'Hare Intl
26h 16m
1 stop
PDX11:09 amPortland
$244
Find similar
Frontier
Jan 8
PDX12:05 pmPortland
24h 00m
1 stop
MDW2:05 pmChicago Midway
Jan 15
MDW11:05 amChicago Midway
25h 28m
2 stops
PDX10:33 amPortland
$255
Find similar
Frontier
Jan 8
PDX12:05 pmPortland
24h 00m
1 stop
MDW2:05 pmChicago Midway
Jan 13
MDW6:30 pmChicago Midway
42h 03m
2 stops
PDX10:33 amPortland
$259
Find similar

Alaska Airlines flights from Portland to Chicago

Our best Alaska Airlines deals on Portland to Chicago flight tickets
Alaska Airlines
Feb 14
PDX6:00 amPortland
6h 11m
1 stop
ORD2:11 pmChicago O'Hare Intl
Feb 17
ORD5:29 pmChicago O'Hare Intl
8h 15m
1 stop
PDX11:44 pmPortland
$236
Find similar
Alaska Airlines
Jan 8
PDX7:10 amPortland
8h 00m
1 stop
ORD5:10 pmChicago O'Hare Intl
Jan 13
ORD6:06 pmChicago O'Hare Intl
6h 40m
1 stop
PDX10:46 pmPortland
$246
Find similar
Alaska Airlines
Feb 1
PDX7:05 amPortland
4h 05m
ORD1:10 pmChicago O'Hare Intl
Feb 5
ORD9:00 amChicago O'Hare Intl
9h 44m
1 stop
PDX4:44 pmPortland
$247
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Portland to Chicago 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 December 11, 2025.
Use the filters below to find and compare flights from Portland to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

PortlandChicago

PDX - ORD

PDXORD

Portland

Sat 2/14

6:00 am-2:11 pm

1 stop6h 11m

Chicago O'Hare Intl

Tue 2/17

5:29 pm-11:44 pm

1 stop8h 15m

$236

PortlandChicago

PDX - ORD

PDXORD

Portland

Wed 1/7

1:30 pm-11:53 pm

1 stop8h 23m

Chicago O'Hare Intl

Wed 1/14

8:50 am-12:46 pm

1 stop5h 56m

$237

PortlandChicago

PDX - MDW

PDXMDW

Portland

Thu 1/8

6:30 am-12:25 pm

Nonstop3h 55m

Chicago Midway

Tue 1/13

4:10 pm-10:30 pm

1 stop8h 20m

$237

PortlandChicago

PDX - ORD

PDXORD

Portland

Wed 1/28

1:24 pm-9:15 pm

1 stop5h 51m

Chicago O'Hare Intl

Fri 1/30

5:16 pm-11:06 pm

1 stop7h 50m

$242

PortlandChicago

PDX - MDW

PDXMDW

Portland

Tue 1/6

6:30 am-12:25 pm

Nonstop3h 55m

Chicago Midway

Thu 1/8

8:10 am-3:40 pm

2 stops9h 30m

$242

PortlandChicago

PDX - ORD

PDXORD

Portland

Thu 1/8

1:24 pm-9:15 pm

1 stop5h 51m

Chicago O'Hare Intl

Mon 1/12

4:15 pm-6:56 pm

Nonstop4h 41m

$243

PortlandChicago

PDX - ORD

PDXORD

Portland

Fri 3/6

12:04 pm-1:07 am

1 stop11h 03m

Chicago O'Hare Intl

Sun 3/8

10:53 am-11:09 am

1 stop26h 16m

$244

PortlandChicago

PDX - ORD

PDXORD

Portland

Thu 1/15

11:59 am-9:24 pm

1 stop7h 25m

Chicago O'Hare Intl

Mon 1/19

8:00 am-10:46 pm

1 stop16h 46m

$249

PortlandChicago

PDX - MDW

PDXMDW

Portland

Thu 1/8

12:05 pm-2:05 pm

1 stop24h 00m

Chicago Midway

Thu 1/15

11:05 am-10:33 am

2 stops25h 28m

$255

PortlandChicago

PDX - RFD

PDXRFD

Portland

Thu 12/25

2:29 pm-7:45 pm

2 stops27h 16m

Chicago Greater Rockford

Sat 1/3

12:15 pm-1:24 pm

1 stop27h 09m

$589

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

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?

The month of August is, on average, the cheapest month to fly to Chicago from Portland, with most prices found around $293. If you’re not able to fly to Chicago in August, then September is your next best option. Flight prices from Portland to Chicago during September average around $293.

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 Friday when prices can be found for as low as $429. 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 $544.

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 $318. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $487.

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 weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $353 when searching 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 $293 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.

Can stopping save me money on Portland to Chicago flights?

No. A direct flight is the cheapest option for a flight between Portland to Chicago.

How have Portland to Chicago flight prices changed over time?

As of December 2025, prices for Portland to Chicago flights are approximately 29% 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

$179

Fastest flight time

3h 44m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from Portland in the past 72 hours is $179. The best round-trip flight deal from Portland to Chicago found on momondo in the last 72 hours is $348.
The fastest flight from Portland to Chicago takes 3h 44m
Direct flights go from Portland to Chicago every day.
There are 3 airports in Chicago. From Portland there are direct flights to Chicago O'Hare Intl (ORD), Chicago Midway (MDW).
Search flight deals

  • 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 44m.

  • 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
FrontierPriceFrom $96Free CancellationRating
5.8
3,084 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $119Free CancellationRating
6.3
8,174 reviews
Search Spirit Airlines flights
DeltaPriceFrom $123Free CancellationRating
7.9
8,009 reviews
Search Delta flights
Hawaiian AirlinesPriceFrom $125Free CancellationRating
7.8
2,818 reviews
Search Hawaiian Airlines flights
American AirlinesPriceFrom $194Free CancellationRating
7.2
11,049 reviews
Search American Airlines flights
Alaska AirlinesPriceFrom $217Free CancellationRating
8.0
11,431 reviews
Search Alaska Airlines flights
United AirlinesPriceFrom $221Free CancellationRating
7.4
9,095 reviews
Search United Airlines flights
SouthwestPriceFrom $238Free CancellationRating
7.9
4,252 reviews
Search Southwest flights

  • Alaska Airlines Flights From Portland to Chicago

    Alaska Airlines flies from Portland to Chicago around 8 times per week, with 11,431 momondo users rating the airline 8.0/10. The cheapest Alaska Airlines deal from Portland to Chicago in the last 72 hours was $217 (round-trip), much lower than the average airfare cost of $346 for Alaska Airlines flights on this route.

  • Southwest Flights From Portland to Chicago

    Another popular option for Portland to Chicago flights is Southwest (7.9/10, 4,252 ratings). Southwest flies from Portland to Chicago around 4 times per week, with deals starting from $238 round-trip and rising to an average price of around $382.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
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
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport