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Cheap flights from Portland to Chicago from $158

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 8/11. 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
1 adult, Economy, 0 bags

Find the cheapest flights from Portland to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
11:30 pm - 5:20 am
PDX
-
MDW
3h 50mnonstop
Southwest Logo
8:25 pm - 10:50 pm
MDW
-
PDX
4h 25mnonstop
$320Southwest
Sat, Jul 18 - Sat, Jul 25
Southwest Logo
11:30 pm - 5:20 am
PDX
-
MDW
3h 50mnonstop
Southwest Logo
5:30 am - 9:45 am
MDW
-
PDX
6h 15m
1 stop
$325Southwest
Tue, Jul 21 - Tue, Jul 28
Southwest Logo
11:30 pm - 5:20 am
PDX
-
MDW
3h 50mnonstop
Southwest Logo
9:50 pm - 12:15 am
MDW
-
PDX
4h 25mnonstop
$326Southwest
Tue, Jul 21 - Sun, Jul 26
Southwest Logo
7:45 pm - 5:00 am
PDX
-
MDW
7h 15m
1 stop
Southwest Logo
8:25 pm - 10:50 pm
MDW
-
PDX
4h 25mnonstop
$330Southwest
Sat, Jul 18 - Sat, Jul 25
Southwest Logo
5:50 am - 4:35 pm
PDX
-
MDW
8h 45m
2 stops
Southwest Logo
8:55 pm - 11:10 pm
MDW
-
PDX
4h 15mnonstop
$331Southwest
Tue, Sep 1 - Tue, Sep 8
Southwest Logo
5:30 pm - 5:00 am
PDX
-
MDW
9h 30m
1 stop
Southwest Logo
5:40 am - 10:40 am
MDW
-
PDX
7h 00m
1 stop
$335Southwest
Sat, Aug 8 - Sat, Aug 15
Southwest Logo
7:55 pm - 5:00 am
PDX
-
MDW
7h 05m
1 stop
Southwest Logo
9:50 pm - 12:15 am
MDW
-
PDX
4h 25mnonstop
$336Southwest
Tue, Jul 21 - Sun, Jul 26
Southwest Logo
11:30 pm - 5:20 am
PDX
-
MDW
3h 50mnonstop
Southwest Logo
9:50 pm - 12:15 am
MDW
-
PDX
4h 25mnonstop
$337Southwest
Thu, Jul 30 - Sun, Aug 2
Southwest Logo
12:30 pm - 10:55 pm
PDX
-
MDW
8h 25m
1 stop
Southwest Logo
12:00 pm - 7:50 pm
MDW
-
PDX
9h 50m
2 stops
$340Southwest
Tue, Aug 11 - Tue, Aug 18
Southwest Logo
7:05 am - 5:10 pm
PDX
-
MDW
8h 05m
2 stops
Southwest Logo
6:30 pm - 8:45 pm
MDW
-
PDX
4h 15mnonstop
$341Southwest
Tue, Aug 11 - Thu, Aug 13

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Southwest flights from Portland to Chicago Midway Airport

Our best Southwest deals on Portland to Chicago Midway Airport flight tickets
Southwest
Jul 18
PDX11:30 pmPortland
3h 50m
MDW5:20 amChicago Midway
Jul 25
MDW8:25 pmChicago Midway
4h 25m
PDX10:50 pmPortland
$320
Southwest
Jul 21
PDX11:30 pmPortland
3h 50m
MDW5:20 amChicago Midway
Jul 28
MDW5:30 amChicago Midway
6h 15m
1 stop
PDX9:45 amPortland
$325
Southwest
Jul 21
PDX11:30 pmPortland
3h 50m
MDW5:20 amChicago Midway
Jul 26
MDW9:50 pmChicago Midway
4h 25m
PDX12:15 amPortland
$326

Delta flights from Portland to Chicago Midway Airport

Our best Delta deals on Portland to Chicago Midway Airport flight tickets
Delta
Aug 13
PDX12:35 amPortland
6h 04m
1 stop
MDW8:39 amChicago Midway
Aug 17
MDW7:25 pmChicago Midway
5h 55m
1 stop
PDX11:20 pmPortland
$357
Delta
Jun 26
PDX12:33 amPortland
6h 04m
1 stop
MDW8:37 amChicago Midway
Jul 4
MDW1:49 pmChicago Midway
8h 28m
1 stop
PDX8:17 pmPortland
$394
Delta
Jun 26
PDX11:15 pmPortland
7h 59m
1 stop
MDW9:14 amChicago Midway
Jul 3
MDW1:49 pmChicago Midway
8h 28m
1 stop
PDX8:17 pmPortland
$426

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 June 17, 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
Quickest round-trip

PortlandChicago

PDX - MDW

PDXMDW

Portland

Sat 7/18

11:30 pm-5:20 am

Nonstop3h 50m

Chicago Midway

Sat 7/25

8:25 pm-10:50 pm

Nonstop4h 25m

$320

PortlandChicago

PDX - MDW

PDXMDW

Portland

Tue 7/21

11:30 pm-5:20 am

Nonstop3h 50m

Chicago Midway

Tue 7/28

5:30 am-9:45 am

1 stop6h 15m

$325

PortlandChicago

PDX - MDW

PDXMDW

Portland

Tue 7/21

11:30 pm-5:20 am

Nonstop3h 50m

Chicago Midway

Sun 7/26

9:50 pm-12:15 am

Nonstop4h 25m

$326

PortlandChicago

PDX - MDW

PDXMDW

Portland

Sat 7/18

7:45 pm-5:00 am

1 stop7h 15m

Chicago Midway

Sat 7/25

8:25 pm-10:50 pm

Nonstop4h 25m

$330

PortlandChicago

PDX - MDW

PDXMDW

Portland

Tue 9/1

5:50 am-4:35 pm

2 stops8h 45m

Chicago Midway

Tue 9/8

8:55 pm-11:10 pm

Nonstop4h 15m

$331

PortlandChicago

PDX - MDW

PDXMDW

Portland

Sat 8/8

5:30 pm-5:00 am

1 stop9h 30m

Chicago Midway

Sat 8/15

5:40 am-10:40 am

1 stop7h 00m

$335

PortlandChicago

PDX - MDW

PDXMDW

Portland

Tue 7/21

7:55 pm-5:00 am

1 stop7h 05m

Chicago Midway

Sun 7/26

9:50 pm-12:15 am

Nonstop4h 25m

$336

PortlandChicago

PDX - MDW

PDXMDW

Portland

Thu 7/30

11:30 pm-5:20 am

Nonstop3h 50m

Chicago Midway

Sun 8/2

9:50 pm-12:15 am

Nonstop4h 25m

$337

PortlandChicago

PDX - MDW

PDXMDW

Portland

Tue 8/11

12:30 pm-10:55 pm

1 stop8h 25m

Chicago Midway

Tue 8/18

12:00 pm-7:50 pm

2 stops9h 50m

$340

PortlandChicago

PDX - MDW

PDXMDW

Portland

Tue 8/11

7:05 am-5:10 pm

2 stops8h 05m

Chicago Midway

Thu 8/13

6:30 pm-8:45 pm

Nonstop4h 15m

$341

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 typical price of a round-trip flight between Portland and Chicago Midway Airport?

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 December is also very affordable. Most momondo users find prices during this month for around $277.

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

According to our data, Tuesday is the cheapest day to fly to Chicago Midway Airport from Portland. The lowest ticket price found for a Tuesday departure recently was $417. 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 $504.

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 $333 when looking at flights departing at noon. Try not to purchase tickets in the evening because they tend to be around $453. 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 Airport flights?

There is only 1 cabin class available to choose from on Portland to Chicago Midway Airport 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 35% 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

$229

Fastest flight time

3h 45m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Portland in the past 72 hours is $229. The best round-trip flight deal from Portland to Chicago Midway Airport found on momondo in the last 72 hours is $422.
The fastest flight from Portland to Chicago Midway Airport takes 3h 45m
Direct flights go from Portland to Chicago Midway Airport every day.
Search flight deals

Frequently asked questions about flying from Portland to Chicago Midway Airport

  • 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 45m.

  • 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 $217Free CancellationRating
7.9
4,235 reviews
Search Southwest flights

  • Southwest Flights From Portland to Chicago Midway Airport

    Southwest operates around 17 flights from Portland to Chicago Midway Airport every week. The average price of these flights found in the last 72 hours has been $357, but momondo users have found Southwest deals from Portland to Chicago Midway Airport from as low as $217 round-trip. Southwest has been scored 7.9/10 in 4,235 reviews.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Portage
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Schererville
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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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