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Cheap flights from Portland to Chicago from $90

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 8/31. 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

Southwest Logo
10:35 am - 4:35 pmPDX-MDW
4h 00mnonstop
Southwest Logo
2:10 pm - 4:25 pmMDW-PDX
4h 15mnonstop
$197Southwest
Find Deal
Sat, Sep 6 - Sat, Sep 13
Southwest Logo
1:35 pm - 7:35 pmPDX-MDW
4h 00mnonstop
Southwest Logo
8:20 pm - 10:35 pmMDW-PDX
4h 15mnonstop
$198Southwest
Find Deal
Fri, Aug 29 - Sun, Aug 31
Southwest Logo
6:10 am - 12:10 pmPDX-MDW
4h 00mnonstop
Southwest Logo
2:10 pm - 4:25 pmMDW-PDX
4h 15mnonstop
$207Southwest
Find Deal
Thu, Sep 4 - Sat, Sep 6
Delta Logo
10:57 pm - 8:35 amPDX-MDW
7h 38m1 stop
Delta Logo
1:43 pm - 8:56 pmMDW-PDX
9h 13m1 stop
$208Delta
Find Deal
Sat, Aug 30 - Tue, Sep 23
Southwest Logo
4:00 pm - 5:10 amPDX-MDW
11h 10m1 stop
Southwest Logo
8:30 pm - 10:45 pmMDW-PDX
4h 15mnonstop
$212Southwest
Find Deal
Sat, Sep 13 - Tue, Sep 16
Delta Logo
12:45 am - 8:53 amPDX-MDW
6h 08m1 stop
Delta Logo
9:20 am - 3:51 pmMDW-PDX
8h 31m1 stop
$217Delta
Find Deal
Fri, Sep 12 - Tue, Sep 30
Delta Logo
10:05 pm - 9:36 amPDX-MDW
9h 31m1 stop
Delta Logo
1:43 pm - 8:56 pmMDW-PDX
9h 13m1 stop
$223Delta
Find Deal
Sat, Aug 30 - Tue, Sep 23
Frontier Logo
6:35 am - 8:54 pmPDX-MDW
12h 19m1 stop
Frontier Logo
2:44 pm - 11:24 pmMDW-PDX
10h 40m1 stop
$248Frontier
Find Deal
Thu, Aug 14 - Sat, Aug 16
Frontier Logo
6:05 am - 3:53 pmPDX-MDW
7h 48m1 stop
Frontier Logo
4:48 pm - 12:12 amMDW-PDX
9h 24m1 stop
$257Frontier
Find Deal
Mon, Sep 15 - Mon, Sep 22
Frontier Logo
11:08 am - 10:01 pmPDX-MDW
8h 53m1 stop
Frontier Logo
4:29 pm - 12:16 amMDW-PDX
9h 47m1 stop
$258Frontier
Find Deal
Thu, Oct 9 - Thu, Oct 16

Southwest flights from Portland to Chicago Midway Airport

Our best Southwest deals on Portland to Chicago Midway Airport flight tickets
Southwest
Sep 6
PDX10:35 amPortland
4h 00m
MDW4:35 pmChicago Midway
Sep 13
MDW2:10 pmChicago Midway
4h 15m
PDX4:25 pmPortland
$197
Find similar
Southwest
Aug 29
PDX1:35 pmPortland
4h 00m
MDW7:35 pmChicago Midway
Aug 31
MDW8:20 pmChicago Midway
4h 15m
PDX10:35 pmPortland
$198
Find similar
Southwest
Sep 4
PDX6:10 amPortland
4h 00m
MDW12:10 pmChicago Midway
Sep 6
MDW2:10 pmChicago Midway
4h 15m
PDX4:25 pmPortland
$207
Find similar

Delta flights from Portland to Chicago Midway Airport

Our best Delta deals on Portland to Chicago Midway Airport flight tickets
Delta
Aug 30
PDX10:57 pmPortland
7h 38m
1 stop
MDW8:35 amChicago Midway
Sep 23
MDW1:43 pmChicago Midway
9h 13m
1 stop
PDX8:56 pmPortland
$208
Find similar
Delta
Sep 12
PDX12:45 amPortland
6h 08m
1 stop
MDW8:53 amChicago Midway
Sep 30
MDW9:20 amChicago Midway
8h 31m
1 stop
PDX3:51 pmPortland
$217
Find similar
Delta
Aug 30
PDX10:05 pmPortland
9h 31m
1 stop
MDW9:36 amChicago Midway
Sep 23
MDW1:43 pmChicago Midway
9h 13m
1 stop
PDX8:56 pmPortland
$223
Find similar

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 August 2, 2025.
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

PortlandChicago

PDX - MDW

PDXMDW

Portland

Sat 9/6

10:35 am-4:35 pm

Nonstop4h 00m

Chicago Midway

Sat 9/13

2:10 pm-4:25 pm

Nonstop4h 15m

$197

PortlandChicago

PDX - MDW

PDXMDW

Portland

Fri 8/29

1:35 pm-7:35 pm

Nonstop4h 00m

Chicago Midway

Sun 8/31

8:20 pm-10:35 pm

Nonstop4h 15m

$198

PortlandChicago

PDX - MDW

PDXMDW

Portland

Thu 9/4

6:10 am-12:10 pm

Nonstop4h 00m

Chicago Midway

Sat 9/6

2:10 pm-4:25 pm

Nonstop4h 15m

$207

PortlandChicago

PDX - MDW

PDXMDW

Portland

Sat 8/30

10:57 pm-8:35 am

1 stop7h 38m

Chicago Midway

Tue 9/23

1:43 pm-8:56 pm

1 stop9h 13m

$208

PortlandChicago

PDX - MDW

PDXMDW

Portland

Sat 9/13

4:00 pm-5:10 am

1 stop11h 10m

Chicago Midway

Tue 9/16

8:30 pm-10:45 pm

Nonstop4h 15m

$212

PortlandChicago

PDX - MDW

PDXMDW

Portland

Fri 9/12

12:45 am-8:53 am

1 stop6h 08m

Chicago Midway

Tue 9/30

9:20 am-3:51 pm

1 stop8h 31m

$217

PortlandChicago

PDX - MDW

PDXMDW

Portland

Sat 8/30

10:05 pm-9:36 am

1 stop9h 31m

Chicago Midway

Tue 9/23

1:43 pm-8:56 pm

1 stop9h 13m

$223

PortlandChicago

PDX - MDW

PDXMDW

Portland

Thu 8/14

6:35 am-8:54 pm

1 stop12h 19m

Chicago Midway

Sat 8/16

2:44 pm-11:24 pm

1 stop10h 40m

$248

PortlandChicago

PDX - MDW

PDXMDW

Portland

Mon 9/15

6:05 am-3:53 pm

1 stop7h 48m

Chicago Midway

Mon 9/22

4:48 pm-12:12 am

1 stop9h 24m

$257

PortlandChicago

PDX - MDW

PDXMDW

Portland

Thu 10/9

11:08 am-10:01 pm

1 stop8h 53m

Chicago Midway

Thu 10/16

4:29 pm-12:16 am

1 stop9h 47m

$258

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 February is, on average, the cheapest month to fly to Chicago Midway Airport from Portland, with most prices found around $253. If you are unable to visit Chicago Midway Airport during the month of February, then departing from Portland during the month September is also very affordable. Most momondo users find prices during this month for around $289.

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

According to our data, Friday is the cheapest day to fly to Chicago Midway Airport from Portland. The lowest ticket price found for a Friday departure recently was $428. 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 $525.

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

Flying to Chicago Midway Airport from Portland in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $289 when looking at flights departing in the afternoon. Try not to purchase tickets in the morning because they tend to be around $451. 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 are 1 cabin classes 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.

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

$90

Fastest flight time

3h 55m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Portland in the past 72 hours is $90. The best round-trip flight deal from Portland to Chicago Midway Airport found on momondo in the last 72 hours is $197.
The fastest flight from Portland to Chicago Midway Airport takes 3h 55m
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 55m.

  • 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
FrontierPriceFrom $108Free CancellationRating
5.8
3,241 reviews
Search Frontier flights
SouthwestPriceFrom $249Free CancellationRating
8.0
4,246 reviews
Search Southwest flights

  • Southwest Flights From Portland to Chicago Midway Airport

    Southwest operates around 7 flights from Portland to Chicago Midway Airport every week. The average price of these flights found in the last 72 hours has been $437, but momondo users have found Southwest deals from Portland to Chicago Midway Airport from as low as $249 round-trip. Southwest has been scored 8.0/10 in 4,246 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
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?

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.

An easier way to manage your Chicago Midway Airport trip

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