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Cheap flights from Portland to Chicago from $113

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 3/16. 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.
Southwest Logo
7:00 pm - 5:05 amPDX-MDW
8h 05m1 stop
Southwest Logo
6:05 pm - 11:35 pmMDW-PDX
7h 30m1 stop
$236Southwest
Find Deal
Sun, Dec 7 - Thu, Dec 18
Southwest Logo
6:30 am - 12:25 pmPDX-MDW
3h 55mnonstop
Southwest Logo
3:35 pm - 6:00 pmMDW-PDX
4h 25mnonstop
$241Southwest
Find Deal
Fri, Jan 9 - Mon, Jan 12
Delta Logo
9:45 pm - 9:51 amPDX-MDW
10h 06m1 stop
Delta Logo
1:05 pm - 10:25 pmMDW-PDX
11h 20m1 stop
$246Delta
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Wed, Apr 15 - Tue, Apr 21
Southwest Logo
6:15 am - 12:10 pmPDX-MDW
3h 55mnonstop
Southwest Logo
8:10 am - 1:55 pmMDW-PDX
7h 45m1 stop
$247Southwest
Find Deal
Fri, Dec 5 - Tue, Dec 9
Delta Logo
12:32 am - 9:19 amPDX-MDW
6h 47m1 stop
Delta Logo
10:49 am - 7:35 pmMDW-PDX
10h 46m1 stop
$248Delta
Find Deal
Mon, Dec 1 - Tue, Dec 9
Southwest Logo
6:15 am - 12:10 pmPDX-MDW
3h 55mnonstop
Southwest Logo
6:00 pm - 10:35 pmMDW-PDX
6h 35m1 stop
$251Southwest
Find Deal
Fri, Dec 5 - Mon, Dec 8
Delta Logo
12:32 am - 9:19 amPDX-MDW
6h 47m1 stop
Delta Logo
1:50 pm - 8:52 pmMDW-PDX
9h 02m1 stop
$252Delta
Find Deal
Mon, Dec 1 - Fri, Dec 5
Delta Logo
12:32 am - 9:19 amPDX-MDW
6h 47m1 stop
Delta Logo
1:50 pm - 8:52 pmMDW-PDX
9h 02m1 stop
$253Delta
Find Deal
Tue, Dec 2 - Mon, Dec 8
Southwest Logo
7:15 am - 5:05 pmPDX-MDW
7h 50m1 stop
Southwest Logo
5:15 pm - 10:30 pmMDW-PDX
7h 15m1 stop
$256Southwest
Find Deal
Fri, Dec 5 - Tue, Dec 9
Southwest Logo
7:15 am - 5:05 pmPDX-MDW
7h 50m1 stop
Southwest Logo
9:50 pm - 12:20 amMDW-PDX
4h 30mnonstop
$257Southwest
Find Deal
Fri, Dec 5 - Sun, Dec 7

Southwest flights from Portland to Chicago Midway Airport

Our best Southwest deals on Portland to Chicago Midway Airport flight tickets
Southwest
Dec 7
PDX7:00 pmPortland
8h 05m
1 stop
MDW5:05 amChicago Midway
Dec 18
MDW6:05 pmChicago Midway
7h 30m
1 stop
PDX11:35 pmPortland
$236
Find similar
Southwest
Jan 9
PDX6:30 amPortland
3h 55m
MDW12:25 pmChicago Midway
Jan 12
MDW3:35 pmChicago Midway
4h 25m
PDX6:00 pmPortland
$241
Find similar
Southwest
Dec 5
PDX6:15 amPortland
3h 55m
MDW12:10 pmChicago Midway
Dec 9
MDW8:10 amChicago Midway
7h 45m
1 stop
PDX1:55 pmPortland
$247
Find similar

Delta flights from Portland to Chicago Midway Airport

Our best Delta deals on Portland to Chicago Midway Airport flight tickets
Delta
Apr 15
PDX9:45 pmPortland
10h 06m
1 stop
MDW9:51 amChicago Midway
Apr 21
MDW1:05 pmChicago Midway
11h 20m
1 stop
PDX10:25 pmPortland
$246
Find similar
Delta
Dec 1
PDX12:32 amPortland
6h 47m
1 stop
MDW9:19 amChicago Midway
Dec 9
MDW10:49 amChicago Midway
10h 46m
1 stop
PDX7:35 pmPortland
$248
Find similar
Delta
Dec 1
PDX12:32 amPortland
6h 47m
1 stop
MDW9:19 amChicago Midway
Dec 5
MDW1:50 pmChicago Midway
9h 02m
1 stop
PDX8:52 pmPortland
$252
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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 November 6, 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

Sun 12/7

7:00 pm-5:05 am

1 stop8h 05m

Chicago Midway

Thu 12/18

6:05 pm-11:35 pm

1 stop7h 30m

$236

PortlandChicago

PDX - MDW

PDXMDW

Portland

Fri 1/9

6:30 am-12:25 pm

Nonstop3h 55m

Chicago Midway

Mon 1/12

3:35 pm-6:00 pm

Nonstop4h 25m

$241

PortlandChicago

PDX - MDW

PDXMDW

Portland

Wed 4/15

9:45 pm-9:51 am

1 stop10h 06m

Chicago Midway

Tue 4/21

1:05 pm-10:25 pm

1 stop11h 20m

$246

PortlandChicago

PDX - MDW

PDXMDW

Portland

Fri 12/5

6:15 am-12:10 pm

Nonstop3h 55m

Chicago Midway

Tue 12/9

8:10 am-1:55 pm

1 stop7h 45m

$247

PortlandChicago

PDX - MDW

PDXMDW

Portland

Mon 12/1

12:32 am-9:19 am

1 stop6h 47m

Chicago Midway

Tue 12/9

10:49 am-7:35 pm

1 stop10h 46m

$248

PortlandChicago

PDX - MDW

PDXMDW

Portland

Fri 12/5

6:15 am-12:10 pm

Nonstop3h 55m

Chicago Midway

Mon 12/8

6:00 pm-10:35 pm

1 stop6h 35m

$251

PortlandChicago

PDX - MDW

PDXMDW

Portland

Mon 12/1

12:32 am-9:19 am

1 stop6h 47m

Chicago Midway

Fri 12/5

1:50 pm-8:52 pm

1 stop9h 02m

$252

PortlandChicago

PDX - MDW

PDXMDW

Portland

Tue 12/2

12:32 am-9:19 am

1 stop6h 47m

Chicago Midway

Mon 12/8

1:50 pm-8:52 pm

1 stop9h 02m

$253

PortlandChicago

PDX - MDW

PDXMDW

Portland

Fri 12/5

7:15 am-5:05 pm

1 stop7h 50m

Chicago Midway

Tue 12/9

5:15 pm-10:30 pm

1 stop7h 15m

$256

PortlandChicago

PDX - MDW

PDXMDW

Portland

Fri 12/5

7:15 am-5:05 pm

1 stop7h 50m

Chicago Midway

Sun 12/7

9:50 pm-12:20 am

Nonstop4h 30m

$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, Friday is the cheapest day to fly to Chicago Midway Airport from Portland. The lowest ticket price found for a Friday departure recently was $418. 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 $490.

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 $391 when looking at flights departing at noon. Try not to purchase tickets in the evening because they tend to be around $636. 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

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

You are more likely to see cheaper flights to Chicago Midway Airport from Portland when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $363 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago Midway Airport from Portland for as low as $260 on momondo.

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?

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

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

$186

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 $186. The best round-trip flight deal from Portland to Chicago Midway Airport found on momondo in the last 72 hours is $287.
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 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 $128Free CancellationRating
5.8
3,116 reviews
Search Frontier flights
Alaska AirlinesPriceFrom $197Free CancellationRating
8.0
11,243 reviews
Search Alaska Airlines flights
SouthwestPriceFrom $246Free CancellationRating
8.0
4,240 reviews
Search Southwest flights
DeltaPriceFrom $268Free CancellationRating
7.9
8,001 reviews
Search Delta flights

  • Southwest Flights From Portland to Chicago Midway Airport

    Southwest operates around 6 flights from Portland to Chicago Midway Airport every week. The average price of these flights found in the last 72 hours has been $404, but momondo users have found Southwest deals from Portland to Chicago Midway Airport from as low as $246 round-trip. Southwest has been scored 8.0/10 in 4,239 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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