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Cheap flights from Portland to Chicago from $99

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 4/14. 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.
Southwest Logo
7:05 pm - 5:40 am
PDX
-
MDW
8h 35m
1 stop
Southwest Logo
5:10 am - 12:55 pm
MDW
-
PDX
9h 45m
1 stop
$227Southwest
Sat, Apr 25 - Sat, May 2
Southwest Logo
11:55 pm - 5:50 am
PDX
-
MDW
3h 55mnonstop
Southwest Logo
10:10 am - 12:30 pm
MDW
-
PDX
4h 20mnonstop
$229Southwest
Sat, Apr 25 - Tue, Apr 28
Southwest Logo
11:55 pm - 5:50 am
PDX
-
MDW
3h 55mnonstop
Southwest Logo
3:40 pm - 8:45 pm
MDW
-
PDX
7h 05m
1 stop
$235Southwest
Sat, Apr 25 - Tue, Apr 28
Southwest Logo
11:55 pm - 5:50 am
PDX
-
MDW
3h 55mnonstop
Southwest Logo
8:50 pm - 11:10 pm
MDW
-
PDX
4h 20mnonstop
$239Southwest
Wed, Apr 15 - Wed, Apr 22
Southwest Logo
11:55 pm - 5:50 am
PDX
-
MDW
3h 55mnonstop
Southwest Logo
4:00 pm - 11:10 pm
MDW
-
PDX
9h 10m
2 stops
$244Southwest
Sat, Apr 25 - Tue, Apr 28
Southwest Logo
6:10 pm - 6:00 am
PDX
-
MDW
9h 50m
1 stop
Southwest Logo
8:50 pm - 11:10 pm
MDW
-
PDX
4h 20mnonstop
$249Southwest
Wed, Apr 15 - Wed, Apr 22
Southwest Logo
11:55 pm - 5:50 am
PDX
-
MDW
3h 55mnonstop
Southwest Logo
6:05 pm - 8:25 pm
MDW
-
PDX
4h 20mnonstop
$251Southwest
Sat, Apr 18 - Sat, Apr 25
Southwest Logo
11:55 pm - 5:50 am
PDX
-
MDW
3h 55mnonstop
Southwest Logo
6:05 pm - 8:25 pm
MDW
-
PDX
4h 20mnonstop
$253Southwest
Thu, May 7 - Sat, May 9
Southwest Logo
7:00 am - 7:35 pm
PDX
-
MDW
10h 35m
2 stops
Southwest Logo
8:50 pm - 11:10 pm
MDW
-
PDX
4h 20mnonstop
$254Southwest
Wed, Apr 15 - Wed, Apr 22
Southwest Logo
5:40 am - 11:35 am
PDX
-
MDW
3h 55mnonstop
Southwest Logo
3:40 pm - 8:45 pm
MDW
-
PDX
7h 05m
1 stop
$257Southwest
Tue, May 12 - Tue, May 12

Southwest flights from Portland to Chicago Midway Airport

Our best Southwest deals on Portland to Chicago Midway Airport flight tickets
Southwest
Apr 25
PDX7:05 pmPortland
8h 35m
1 stop
MDW5:40 amChicago Midway
May 2
MDW5:10 amChicago Midway
9h 45m
1 stop
PDX12:55 pmPortland
$227
Southwest
Apr 25
PDX11:55 pmPortland
3h 55m
MDW5:50 amChicago Midway
Apr 28
MDW10:10 amChicago Midway
4h 20m
PDX12:30 pmPortland
$229
Southwest
Apr 25
PDX11:55 pmPortland
3h 55m
MDW5:50 amChicago Midway
Apr 28
MDW3:40 pmChicago Midway
7h 05m
1 stop
PDX8:45 pmPortland
$235

Delta flights from Portland to Chicago Midway Airport

Our best Delta deals on Portland to Chicago Midway Airport flight tickets
Delta
Apr 25
PDX6:00 amPortland
5h 32m
1 stop
MDW1:32 pmChicago Midway
Apr 28
MDW2:12 pmChicago Midway
7h 55m
1 stop
PDX8:07 pmPortland
$291
Delta
Mar 23
PDX11:15 pmPortland
7h 38m
1 stop
MDW8:53 amChicago Midway
Apr 3
MDW2:05 pmChicago Midway
8h 20m
1 stop
PDX8:25 pmPortland
$423
Delta
Mar 26
PDX6:30 amPortland
8h 52m
1 stop
MDW5:22 pmChicago Midway
Mar 31
MDW12:47 pmChicago Midway
8h 13m
1 stop
PDX7:00 pmPortland
$482

momondo Fare Finder

 
Customize your flight search to find flights from Portland to Chicago Midway 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 March 14, 2026.
Use the filters below to find and compare flights from Portland to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

PortlandChicago

PDX - MDW

PDXMDW

Portland

Sat 4/25

7:05 pm-5:40 am

1 stop8h 35m

Chicago Midway

Sat 5/2

5:10 am-12:55 pm

1 stop9h 45m

$227
Quickest round-trip

PortlandChicago

PDX - MDW

PDXMDW

Portland

Sat 4/25

11:55 pm-5:50 am

Nonstop3h 55m

Chicago Midway

Tue 4/28

10:10 am-12:30 pm

Nonstop4h 20m

$229

PortlandChicago

PDX - MDW

PDXMDW

Portland

Sat 4/25

11:55 pm-5:50 am

Nonstop3h 55m

Chicago Midway

Tue 4/28

3:40 pm-8:45 pm

1 stop7h 05m

$235

PortlandChicago

PDX - MDW

PDXMDW

Portland

Wed 4/15

11:55 pm-5:50 am

Nonstop3h 55m

Chicago Midway

Wed 4/22

8:50 pm-11:10 pm

Nonstop4h 20m

$239

PortlandChicago

PDX - MDW

PDXMDW

Portland

Sat 4/25

11:55 pm-5:50 am

Nonstop3h 55m

Chicago Midway

Tue 4/28

4:00 pm-11:10 pm

2 stops9h 10m

$244

PortlandChicago

PDX - MDW

PDXMDW

Portland

Wed 4/15

6:10 pm-6:00 am

1 stop9h 50m

Chicago Midway

Wed 4/22

8:50 pm-11:10 pm

Nonstop4h 20m

$249

PortlandChicago

PDX - MDW

PDXMDW

Portland

Sat 4/18

11:55 pm-5:50 am

Nonstop3h 55m

Chicago Midway

Sat 4/25

6:05 pm-8:25 pm

Nonstop4h 20m

$251

PortlandChicago

PDX - MDW

PDXMDW

Portland

Thu 5/7

11:55 pm-5:50 am

Nonstop3h 55m

Chicago Midway

Sat 5/9

6:05 pm-8:25 pm

Nonstop4h 20m

$253

PortlandChicago

PDX - MDW

PDXMDW

Portland

Wed 4/15

7:00 am-7:35 pm

2 stops10h 35m

Chicago Midway

Wed 4/22

8:50 pm-11:10 pm

Nonstop4h 20m

$254

PortlandChicago

PDX - MDW

PDXMDW

Portland

Tue 5/12

5:40 am-11:35 am

Nonstop3h 55m

Chicago Midway

Tue 5/12

3:40 pm-8:45 pm

1 stop7h 05m

$257

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 Midway 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 Midway Airport?

The month of January is, on average, the cheapest month to fly to Chicago Midway Airport from Portland, with most prices found around $197. If you are unable to visit Chicago Midway Airport during the month of January, then departing from Portland during the month September is also very affordable. Most momondo users find prices during this month for around $242.

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

According to our data, Thursday is the cheapest day to fly to Chicago Midway Airport from Portland. The lowest ticket price found for a Thursday departure recently was $407. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. 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 $470.

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

Flying to Chicago Midway Airport from Portland at noon is the least expensive time of day to depart. momondo users have found prices as low as $372 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $431. 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 Midway flight route?

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

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

There is only 1 cabin class available to choose from on Portland to Chicago Midway 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 Midway Airport flights?

You could potentially save up to 1% on your flight if you consider stops on a Portland to Chicago Midway Airport flight.

When to book flights from Portland to Chicago Midway Airport

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

Cheap Portland to Chicago Midway Airport (PDX to MDW) flight deals and tips

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

Best Price Found

$178

Fastest flight time

3h 50m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Portland in the past 72 hours is $178. The best round-trip flight deal from Portland to Chicago Midway Airport found on momondo in the last 72 hours is $374.
The fastest flight from Portland to Chicago Midway Airport takes 3h 50m
Direct flights go from Portland to Chicago Midway Airport every day.
Search flight deals

  • How far is Portland to Chicago Midway by plane?

    Chicago Midway is 1749.8 mi away from Portland. By plane, this route typically takes 3h 50m.

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

    Prices for flights from Portland Airport to Chicago Midway Airport were last updated today.

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

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

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

    The travel and health documents required for your trip to Chicago Midway 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 Midway 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 Midway Airport?

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

Best airlines flying from Portland to Chicago Midway Airport

Compare and see reviews for airlines that fly from Portland to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $231Free CancellationRating
8.0
4,317 reviews
Search Southwest flights
DeltaPriceFrom $268Free CancellationRating
7.9
8,291 reviews
Search Delta flights

  • Southwest Flights From Portland to Chicago Midway Airport

    Southwest operates around 11 flights from Portland to Chicago Midway Airport every week. The average price of these flights found in the last 72 hours has been $369, but momondo users have found Southwest deals from Portland to Chicago Midway Airport from as low as $231 round-trip. Southwest has been scored 8.0/10 in 4,317 reviews.

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
Valparaiso
Schererville
Munster
Crown Point
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Portland to Chicago?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Portland to Chicago. Millions of users trust and use momondo every year so you are in good hands.

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?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Portland to Chicago.

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

Yes momondo offers price alerts on flights to Chicago from Portland. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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