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Cheap flights from Portland to Chicago from $179

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
10:10 am - 7:40 pmPDX  Portland-MDW Chicago Midway
7h 30m2 stops Denver Intl Cincinnati Cinci./N. Kentucky
Southwest Logo
7:35 pm - 1:15 amMDW  Chicago Midway-PDX Portland
7h 40m1 stop Las Vegas Harry Reid Intl
$354Southwest
Tue, Dec 8 - Sun, Dec 20
Southwest Logo
10:10 am - 7:40 pmPDX  Portland-MDW Chicago Midway
7h 30m2 stops Denver Intl Cincinnati Cinci./N. Kentucky
Southwest Logo
7:35 pm - 1:15 amMDW  Chicago Midway-PDX Portland
7h 40m1 stop Las Vegas Harry Reid Intl
$354Southwest
Tue, Dec 8 - Sun, Dec 20
Southwest Logo
10:15 am - 10:00 pmPDX  Portland-MDW Chicago Midway
9h 45m1 stop San Diego
Southwest Logo
6:05 am - 10:40 amMDW  Chicago Midway-PDX Portland
6h 35m1 stop Denver Intl
$356Southwest
Thu, Dec 10 - Tue, Dec 15
Southwest Logo
11:20 am - 5:05 pmPDX  Portland-MDW Chicago Midway
3h 45mnonstop
Southwest Logo
10:00 am - 12:35 pmMDW  Chicago Midway-PDX Portland
4h 35mnonstop
$357Southwest
Tue, Nov 17 - Wed, Nov 18
Southwest Logo
6:55 pm - 5:45 amPDX  Portland-MDW Chicago Midway
8h 50m1 stop Phoenix Sky Harbor Intl
Southwest Logo
5:50 am - 10:15 amMDW  Chicago Midway-PDX Portland
6h 25m1 stop Denver Intl
$358Southwest
Mon, Mar 1 - Sun, Mar 7
Southwest Logo
10:15 am - 10:00 pmPDX  Portland-MDW Chicago Midway
9h 45m1 stop San Diego
Southwest Logo
6:05 am - 1:10 pmMDW  Chicago Midway-PDX Portland
9h 05m1 stop Denver Intl
$358Southwest
Thu, Dec 31 - Tue, Jan 5
Delta Logo
6:20 am - 4:53 pmPDX  Portland-MDW Chicago Midway
8h 33m1 stop Minneapolis St Paul
Delta Logo
9:38 am - 6:58 pmMDW  Chicago Midway-PDX Portland
11h 20m2 stops Detroit Metropolitan Wayne County Seattle/Tacoma Intl
$359Delta
Sun, Jan 10 - Sat, Jan 16
Delta Logo
5:30 am - 4:39 pmPDX  Portland-MDW Chicago Midway
9h 09m2 stops Seattle/Tacoma Intl Minneapolis St Paul
Delta Logo
1:31 pm - 9:57 pmMDW  Chicago Midway-PDX Portland
10h 26m2 stops Detroit Metropolitan Wayne County Seattle/Tacoma Intl
$359Delta
Tue, Nov 17 - Mon, Nov 23
Southwest Logo
6:00 am - 11:50 amPDX  Portland-MDW Chicago Midway
3h 50mnonstop
Southwest Logo
10:25 am - 1:00 pmMDW  Chicago Midway-PDX Portland
4h 35mnonstop
$359Southwest
Tue, Dec 1 - Sat, Dec 5
Southwest Logo
6:55 am - 5:20 pmPDX  Portland-MDW Chicago Midway
8h 25m2 stops Las Vegas Harry Reid Intl Omaha Eppley Airfield
Southwest Logo
7:35 pm - 1:15 amMDW  Chicago Midway-PDX Portland
7h 40m1 stop Las Vegas Harry Reid Intl
$359Southwest
Wed, Dec 16 - Sun, Dec 20

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Delta flights from Portland to Chicago Midway Airport

Our best Delta deals on Portland to Chicago Midway Airport flight tickets
Delta
Nov 16
PDX11:20 pmPortland
8h 26m
1 stop
MDW9:46 amChicago Midway
Nov 23
MDW10:34 amChicago Midway
13h 23m
2 stops
PDX9:57 pmPortland
$358
Delta
Nov 17
PDX5:30 amPortland
9h 09m
2 stops
MDW4:39 pmChicago Midway
Nov 23
MDW1:31 pmChicago Midway
10h 26m
2 stops
PDX9:57 pmPortland
$359
Delta
Nov 14
PDX12:35 amPortland
6h 15m
1 stop
MDW8:50 amChicago Midway
Nov 21
MDW5:29 pmChicago Midway
8h 17m
1 stop
PDX11:46 pmPortland
$364

Southwest flights from Portland to Chicago Midway Airport

Our best Southwest deals on Portland to Chicago Midway Airport flight tickets
Southwest
Dec 8
PDX10:10 amPortland
7h 30m
2 stops
MDW7:40 pmChicago Midway
Dec 20
MDW7:35 pmChicago Midway
7h 40m
1 stop
PDX1:15 amPortland
$354
Southwest
Dec 10
PDX10:15 amPortland
9h 45m
1 stop
MDW10:00 pmChicago Midway
Dec 15
MDW6:05 amChicago Midway
6h 35m
1 stop
PDX10:40 amPortland
$356
Southwest
Nov 17
PDX11:20 amPortland
3h 45m
MDW5:05 pmChicago Midway
Nov 18
MDW10:00 amChicago Midway
4h 35m
PDX12:35 pmPortland
$357

momondo Fare Finder

 
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 Portland - MDW Chicago Midway

PDXMDW

Portland

Tue 12/8

10:10 am-7:40 pm

2 stops7h 30m

Chicago Midway

Sun 12/20

7:35 pm-1:15 am

1 stop7h 40m

$354

PortlandChicago

PDX Portland - MDW Chicago Midway

PDXMDW

Portland

Tue 12/8

10:10 am-7:40 pm

2 stops7h 30m

Chicago Midway

Sun 12/20

7:35 pm-1:15 am

1 stop7h 40m

$354

PortlandChicago

PDX Portland - MDW Chicago Midway

PDXMDW

Portland

Thu 12/10

10:15 am-10:00 pm

1 stop9h 45m

Chicago Midway

Tue 12/15

6:05 am-10:40 am

1 stop6h 35m

$356
Quickest round-trip

PortlandChicago

PDX Portland - MDW Chicago Midway

PDXMDW

Portland

Tue 11/17

11:20 am-5:05 pm

Nonstop3h 45m

Chicago Midway

Wed 11/18

10:00 am-12:35 pm

Nonstop4h 35m

$357

PortlandChicago

PDX Portland - MDW Chicago Midway

PDXMDW

Portland

Mon 3/1

6:55 pm-5:45 am

1 stop8h 50m

Chicago Midway

Sun 3/7

5:50 am-10:15 am

1 stop6h 25m

$358

PortlandChicago

PDX Portland - MDW Chicago Midway

PDXMDW

Portland

Thu 12/31

10:15 am-10:00 pm

1 stop9h 45m

Chicago Midway

Tue 1/5

6:05 am-1:10 pm

1 stop9h 05m

$358

PortlandChicago

PDX Portland - MDW Chicago Midway

PDXMDW

Portland

Sun 1/10

6:20 am-4:53 pm

1 stop8h 33m

Chicago Midway

Sat 1/16

9:38 am-6:58 pm

2 stops11h 20m

$359

PortlandChicago

PDX Portland - MDW Chicago Midway

PDXMDW

Portland

Tue 11/17

5:30 am-4:39 pm

2 stops9h 09m

Chicago Midway

Mon 11/23

1:31 pm-9:57 pm

2 stops10h 26m

$359

PortlandChicago

PDX Portland - MDW Chicago Midway

PDXMDW

Portland

Tue 12/1

6:00 am-11:50 am

Nonstop3h 50m

Chicago Midway

Sat 12/5

10:25 am-1:00 pm

Nonstop4h 35m

$359

PortlandChicago

PDX Portland - MDW Chicago Midway

PDXMDW

Portland

Wed 12/16

6:55 am-5:20 pm

2 stops8h 25m

Chicago Midway

Sun 12/20

7:35 pm-1:15 am

1 stop7h 40m

$359

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?

Prices are currently low for flights on this route.

Typical prices usually range from $417 to $561.
The lowest price recently found on this route was $354.

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 $293. If you are unable to visit Chicago Midway Airport during the month of February, then departing from Portland during the month April is also very affordable. Most momondo users find prices during this month for around $297.

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 $434. 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 $557.

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 evening is the least expensive time of day to depart. momondo users have found prices as low as $456 when looking at flights departing in the evening. Try not to purchase tickets in the morning because they tend to be around $467. 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 43% 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

$179

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 $179. The best round-trip flight deal from Portland to Chicago Midway Airport found on momondo in the last 72 hours is $354.
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 $266Free CancellationRating
7.9
4,224 reviews
Search Southwest flights

  • Southwest Flights From Portland to Chicago Midway Airport

    Southwest operates around 10 flights from Portland to Chicago Midway Airport every week. The average price of these flights found in the last 72 hours has been $374, but momondo users have found Southwest deals from Portland to Chicago Midway Airport from as low as $266 round-trip. Southwest has been scored 7.9/10 in 4,224 reviews.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Portage
Saint Joseph
Benton Harbor
Lansing
Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
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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