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Cheap flights from Portland to Chicago from $161

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 - 5:25 amPDX  Portland-MDW Chicago Midway
3h 55mnonstop
Southwest Logo
8:55 pm - 11:15 pmMDW  Chicago Midway-PDX Portland
4h 20mnonstop
$357Southwest
Wed, Sep 16 - Wed, Sep 23
Southwest Logo
10:50 am - 4:40 pmPDX  Portland-MDW Chicago Midway
3h 50mnonstop
Southwest Logo
7:50 pm - 10:20 pmMDW  Chicago Midway-PDX Portland
4h 30mnonstop
$357Southwest
Mon, Feb 1 - Thu, Feb 4
Southwest Logo
11:35 pm - 5:25 amPDX  Portland-MDW Chicago Midway
3h 50mnonstop
Southwest Logo
9:45 pm - 12:10 amMDW  Chicago Midway-PDX Portland
4h 25mnonstop
$357Southwest
Mon, Oct 5 - Thu, Oct 8
Southwest Logo
11:30 pm - 5:25 amPDX  Portland-MDW Chicago Midway
3h 55mnonstop
Southwest Logo
8:50 pm - 11:10 pmMDW  Chicago Midway-PDX Portland
4h 20mnonstop
$357Southwest
Wed, Sep 9 - Mon, Sep 14
Southwest Logo
11:30 pm - 5:15 amPDX  Portland-MDW Chicago Midway
3h 45mnonstop
Southwest Logo
9:15 pm - 11:55 pmMDW  Chicago Midway-PDX Portland
4h 40mnonstop
$357Southwest
Fri, Nov 6 - Mon, Nov 9
Southwest Logo
11:30 pm - 5:25 amPDX  Portland-MDW Chicago Midway
3h 55mnonstop
Southwest Logo
9:45 pm - 12:10 amMDW  Chicago Midway-PDX Portland
4h 25mnonstop
$357Southwest
Sun, Sep 27 - Thu, Oct 1
Southwest Logo
11:30 pm - 5:25 amPDX  Portland-MDW Chicago Midway
3h 55mnonstop
Southwest Logo
8:55 pm - 11:15 pmMDW  Chicago Midway-PDX Portland
4h 20mnonstop
$357Southwest
Thu, Sep 10 - Wed, Sep 16
Southwest Logo
11:30 pm - 5:25 amPDX  Portland-MDW Chicago Midway
3h 55mnonstop
Southwest Logo
8:55 pm - 11:15 pmMDW  Chicago Midway-PDX Portland
4h 20mnonstop
$357Southwest
Mon, Sep 14 - Wed, Sep 16
Delta Logo
12:25 am - 8:48 amPDX  Portland-MDW Chicago Midway
6h 23m1 stop Minneapolis St Paul
Delta Logo
7:13 pm - 11:10 pmMDW  Chicago Midway-PDX Portland
5h 57m1 stop Minneapolis St Paul
$377Delta
Sat, Sep 12 - Mon, Sep 14
Delta Logo
12:25 am - 8:48 amPDX  Portland-MDW Chicago Midway
6h 23m1 stop Minneapolis St Paul
Delta Logo
7:13 pm - 11:10 pmMDW  Chicago Midway-PDX Portland
5h 57m1 stop Minneapolis St Paul
$377Delta
Tue, Sep 8 - Mon, Sep 14

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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
Sep 10
PDX11:30 pmPortland
3h 55m
MDW5:25 amChicago Midway
Sep 16
MDW8:55 pmChicago Midway
4h 20m
PDX11:15 pmPortland
$357
Southwest
Sep 11
PDX8:00 amPortland
7h 00m
1 stop
MDW5:00 pmChicago Midway
Sep 15
MDW8:55 pmChicago Midway
4h 20m
PDX11:15 pmPortland
$363
Southwest
Sep 10
PDX11:30 pmPortland
3h 55m
MDW5:25 amChicago Midway
Sep 16
MDW10:05 amChicago Midway
7h 15m
1 stop
PDX3:20 pmPortland
$367

Delta flights from Portland to Chicago Midway Airport

Our best Delta deals on Portland to Chicago Midway Airport flight tickets
Delta
Oct 10
PDX6:00 amPortland
8h 47m
1 stop
MDW4:47 pmChicago Midway
Oct 15
MDW10:01 amChicago Midway
15h 43m
1 stop
PDX11:44 pmPortland
$389
Delta
Sep 10
PDX12:25 amPortland
6h 23m
1 stop
MDW8:48 amChicago Midway
Sep 14
MDW7:13 pmChicago Midway
5h 57m
1 stop
PDX11:10 pmPortland
$393
Delta
Sep 8
PDX12:25 amPortland
6h 23m
1 stop
MDW8:48 amChicago Midway
Sep 15
MDW1:00 pmChicago Midway
10h 47m
1 stop
PDX9:47 pmPortland
$397

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
Quickest round-trip

PortlandChicago

PDX Portland - MDW Chicago Midway

PDXMDW

Portland

Wed 9/16

11:30 pm-5:25 am

Nonstop3h 55m

Chicago Midway

Wed 9/23

8:55 pm-11:15 pm

Nonstop4h 20m

$357

PortlandChicago

PDX Portland - MDW Chicago Midway

PDXMDW

Portland

Mon 2/1

10:50 am-4:40 pm

Nonstop3h 50m

Chicago Midway

Thu 2/4

7:50 pm-10:20 pm

Nonstop4h 30m

$357

PortlandChicago

PDX Portland - MDW Chicago Midway

PDXMDW

Portland

Mon 10/5

11:35 pm-5:25 am

Nonstop3h 50m

Chicago Midway

Thu 10/8

9:45 pm-12:10 am

Nonstop4h 25m

$357

PortlandChicago

PDX Portland - MDW Chicago Midway

PDXMDW

Portland

Wed 9/9

11:30 pm-5:25 am

Nonstop3h 55m

Chicago Midway

Mon 9/14

8:50 pm-11:10 pm

Nonstop4h 20m

$357

PortlandChicago

PDX Portland - MDW Chicago Midway

PDXMDW

Portland

Fri 11/6

11:30 pm-5:15 am

Nonstop3h 45m

Chicago Midway

Mon 11/9

9:15 pm-11:55 pm

Nonstop4h 40m

$357

PortlandChicago

PDX Portland - MDW Chicago Midway

PDXMDW

Portland

Sun 9/27

11:30 pm-5:25 am

Nonstop3h 55m

Chicago Midway

Thu 10/1

9:45 pm-12:10 am

Nonstop4h 25m

$357

PortlandChicago

PDX Portland - MDW Chicago Midway

PDXMDW

Portland

Thu 9/10

11:30 pm-5:25 am

Nonstop3h 55m

Chicago Midway

Wed 9/16

8:55 pm-11:15 pm

Nonstop4h 20m

$357

PortlandChicago

PDX Portland - MDW Chicago Midway

PDXMDW

Portland

Mon 9/14

11:30 pm-5:25 am

Nonstop3h 55m

Chicago Midway

Wed 9/16

8:55 pm-11:15 pm

Nonstop4h 20m

$357

PortlandChicago

PDX Portland - MDW Chicago Midway

PDXMDW

Portland

Sat 9/12

12:25 am-8:48 am

1 stop6h 23m

Chicago Midway

Mon 9/14

7:13 pm-11:10 pm

1 stop5h 57m

$377

PortlandChicago

PDX Portland - MDW Chicago Midway

PDXMDW

Portland

Tue 9/8

12:25 am-8:48 am

1 stop6h 23m

Chicago Midway

Mon 9/14

7:13 pm-11:10 pm

1 stop5h 57m

$377

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 $382 to $427.
The lowest price recently found on this route was $357.

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 $432. 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 $521.

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 $405 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $458. 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 31% 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

$161

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 $161. The best round-trip flight deal from Portland to Chicago Midway Airport found on momondo in the last 72 hours is $357.
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
8.0
4,217 reviews
Search Southwest flights

  • Southwest Flights From Portland to Chicago Midway Airport

    Southwest operates around 23 flights from Portland to Chicago Midway Airport every week. The average price of these flights found in the last 72 hours has been $365, but momondo users have found Southwest deals from Portland to Chicago Midway Airport from as low as $266 round-trip. Southwest has been scored 8.0/10 in 4,217 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
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
Monticello
Porter
Crown Point
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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