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Cheap flights from Portland to Chicago Midway Airport from $59

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 Midway Airport departing on 1/23. 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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Find the cheapest flights from Portland to Chicago

Cheap round-trip flights

These are some of the best round-trip flight deals from Portland to Chicago that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Portland to Chicago.

Cheap last minute flights

Planning a quick getaway from Portland to Chicago? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Chicago, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Portland to Chicago

Find recent round-trip train or bus tickets from Portland to Chicago.

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
12:03 pm - 12:17 amPDX-MDW
10h 14m1 stop
8:44 pm - 8:40 amMDW-PDX
13h 56m1 stop
$108Frontier
Find Deal
Mon, Feb 10 - Sat, Feb 22
7:35 am - 12:17 amPDX-MDW
14h 42m1 stop
7:05 am - 12:37 amMDW-PDX
19h 32m1 stop
$115Frontier
Find Deal
Wed, Feb 5 - Wed, Feb 12
7:35 am - 12:17 amPDX-MDW
14h 42m1 stop
8:15 am - 11:01 amMDW-PDX
28h 46m1 stop
$120Frontier
Find Deal
Wed, Jan 29 - Wed, Feb 5
7:35 am - 12:17 amPDX-MDW
14h 42m1 stop
7:05 am - 12:37 amMDW-PDX
19h 32m1 stop
$121Frontier
Find Deal
Wed, Feb 5 - Wed, Feb 12
8:00 am - 1:55 pmPDX-MDW
3h 55mnonstop
8:30 am - 10:55 amMDW-PDX
4h 25mnonstop
$208Southwest
Find Deal
Thu, Jan 16 - Wed, Jan 22
9:00 am - 2:55 pmPDX-MDW
3h 55mnonstop
8:10 pm - 10:40 pmMDW-PDX
4h 30mnonstop
$218Southwest
Find Deal
Fri, Jan 31 - Sun, Feb 2
12:45 am - 9:39 amPDX-MDW
6h 54m1 stop
1:26 pm - 8:35 pmMDW-PDX
9h 09m1 stop
$236Delta
Find Deal
Sun, Jan 19 - Mon, Jan 27
5:26 pm - 11:44 amPDX-MDW
16h 18m2 stops
1:26 pm - 8:36 pmMDW-PDX
9h 10m1 stop
Thu, Jan 16 - Wed, Jan 22
12:45 pm - 10:20 pmPDX-MDW
7h 35m1 stop
1:26 pm - 5:32 pmMDW-PDX
6h 06m1 stop
$252Delta
Find Deal
Tue, Jan 28 - Mon, Feb 10
5:30 pm - 12:17 amPDX-MDW
28h 47m3 stops
4:48 pm - 12:37 amMDW-PDX
33h 49m2 stops
Mon, Feb 10 - Sat, Feb 22
12:03 pm - 12:17 amPDX-MDW
10h 14m1 stop
$59Frontier
Find Deal
Thu, Jan 23
12:03 pm - 12:17 amPDX-MDW
10h 14m1 stop
$60Frontier
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Mon, Feb 10
9:00 am - 2:55 pmPDX-MDW
3h 55mnonstop
$99Southwest
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Wed, Jan 22
12:45 am - 9:39 amPDX-MDW
6h 54m1 stop
$104Delta
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Mon, Jan 20
12:45 am - 9:39 amPDX-MDW
6h 54m1 stop
$108Delta
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Tue, Jan 21
9:00 am - 2:55 pmPDX-MDW
3h 55mnonstop
$109Southwest
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Thu, Jan 23
11:16 am - 10:09 amPDX-MDW
20h 53m2 stops
$151Allegiant Air
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Thu, Mar 6
12:45 pm - 10:09 amPDX-MDW
19h 24m2 stops
$168Allegiant Air
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Thu, Mar 13
7:20 am - 5:36 pmPDX-MDW
32h 16m3 stops
Wed, Mar 5
7:20 am - 5:36 pmPDX-MDW
32h 16m3 stops
Wed, Mar 5
6:19 pm - 9:49 amPDX-MDW
13h 30m1 stop
10:27 pm - 3:59 pmMDW-PDX
19h 32m1 stop
$622Frontier
Find Deal
Wed, Dec 25 - Wed, Jan 1
11:30 am - 5:25 pmPDX-MDW
3h 55mnonstop
6:50 pm - 9:20 pmMDW-PDX
4h 30mnonstop
$628Southwest
Find Deal
Tue, Dec 24 - Thu, Jan 2
10:10 am - 10:00 pmPDX-MDW
9h 50m1 stop
6:50 pm - 9:20 pmMDW-PDX
4h 30mnonstop
$637Southwest
Find Deal
Tue, Dec 24 - Thu, Jan 2
6:05 am - 5:15 pmPDX-MDW
9h 10m2 stops
6:50 pm - 9:20 pmMDW-PDX
4h 30mnonstop
$642Southwest
Find Deal
Tue, Dec 24 - Thu, Jan 2
10:46 am - 5:33 amPDX-MDW
16h 47m1 stop
10:04 pm - 3:44 pmMDW-PDX
19h 40m1 stop
$670Frontier
Find Deal
Thu, Dec 26 - Mon, Dec 30
11:30 am - 5:25 pmPDX-MDW
3h 55mnonstop
5:25 pm - 10:35 pmMDW-PDX
7h 10m1 stop
$682Southwest
Find Deal
Wed, Dec 25 - Wed, Jan 1
6:19 pm - 9:49 amPDX-MDW
13h 30m1 stop
7:00 am - 3:44 pmMDW-PDX
10h 44m1 stop
$718Frontier
Find Deal
Wed, Dec 25 - Sat, Dec 28
6:20 am - 5:11 pmPDX-MDW
8h 51m1 stop
12:10 pm - 6:59 pmMDW-PDX
8h 49m1 stop
$797Delta
Find Deal
Tue, Dec 24 - Fri, Jan 3
6:20 am - 5:11 pmPDX-MDW
8h 51m1 stop
5:04 pm - 9:13 pmMDW-PDX
30h 09m2 stops
$885Delta
Find Deal
Tue, Dec 24 - Thu, Jan 2
6:20 am - 5:11 pmPDX-MDW
8h 51m1 stop
5:04 pm - 8:21 pmMDW-PDX
29h 17m1 stop
$897Delta
Find Deal
Tue, Dec 24 - Thu, Jan 2
8:00 am - 1:55 pmPDX-MDW
3h 55mnonstop
8:30 am - 10:55 amMDW-PDX
4h 25mnonstop
$208Southwest
Find Deal
Thu, Jan 16 - Wed, Jan 22
9:00 am - 2:55 pmPDX-MDW
3h 55mnonstop
8:10 pm - 10:40 pmMDW-PDX
4h 30mnonstop
$218Southwest
Find Deal
Fri, Jan 31 - Sun, Feb 2
8:00 am - 1:55 pmPDX-MDW
3h 55mnonstop
8:10 pm - 10:40 pmMDW-PDX
4h 30mnonstop
$258Southwest
Find Deal
Fri, Jan 17 - Mon, Jan 20
8:00 am - 1:55 pmPDX-MDW
3h 55mnonstop
8:30 am - 10:55 amMDW-PDX
4h 25mnonstop
$263Southwest
Find Deal
Fri, Jan 17 - Sun, Jan 19
8:00 am - 1:55 pmPDX-MDW
3h 55mnonstop
8:30 am - 10:55 amMDW-PDX
4h 25mnonstop
$274Southwest
Find Deal
Mon, Jan 20 - Mon, Jan 27
12:10 pm - 6:05 pmPDX-MDW
3h 55mnonstop
5:45 pm - 8:05 pmMDW-PDX
4h 20mnonstop
$304Southwest
Find Deal
Wed, Mar 12 - Wed, Mar 19
9:00 am - 2:55 pmPDX-MDW
3h 55mnonstop
8:10 pm - 10:40 pmMDW-PDX
4h 30mnonstop
$319Southwest
Find Deal
Fri, Jan 10 - Sun, Jan 12
7:50 am - 1:45 pmPDX-MDW
3h 55mnonstop
8:30 am - 10:55 amMDW-PDX
4h 25mnonstop
$424Southwest
Find Deal
Sat, Jan 4 - Wed, Jan 8
12:55 pm - 6:50 pmPDX-MDW
3h 55mnonstop
2:50 pm - 5:10 pmMDW-PDX
4h 20mnonstop
$430Southwest
Find Deal
Mon, Mar 31 - Mon, Apr 7
11:30 am - 5:25 pmPDX-MDW
3h 55mnonstop
7:40 pm - 10:10 pmMDW-PDX
4h 30mnonstop
$453Southwest
Find Deal
Wed, Jan 1 - Mon, Jan 6

Frontier flights from Portland to Chicago Midway Airport

Our best Frontier deals on Portland to Chicago Midway Airport flight tickets
Frontier
Feb 10
PDX12:03 pmPortland
10h 14m
1 stop
MDW12:17 amChicago Midway
Feb 22
MDW8:44 pmChicago Midway
13h 56m
1 stop
PDX8:40 amPortland
Frontier
Feb 5
PDX7:35 amPortland
14h 42m
1 stop
MDW12:17 amChicago Midway
Feb 12
MDW7:05 amChicago Midway
19h 32m
1 stop
PDX12:37 amPortland
Frontier
Jan 29
PDX7:35 amPortland
14h 42m
1 stop
MDW12:17 amChicago Midway
Feb 5
MDW8:15 amChicago Midway
28h 46m
1 stop
PDX11:01 amPortland

Southwest flights from Portland to Chicago Midway Airport

Our best Southwest deals on Portland to Chicago Midway Airport flight tickets
Southwest
Jan 16
PDX8:00 amPortland
3h 55m
MDW1:55 pmChicago Midway
Jan 22
MDW8:30 amChicago Midway
4h 25m
PDX10:55 amPortland
Southwest
Jan 31
PDX9:00 amPortland
3h 55m
MDW2:55 pmChicago Midway
Feb 2
MDW8:10 pmChicago Midway
4h 30m
PDX10:40 pmPortland
Southwest
Jan 17
PDX8:00 amPortland
3h 55m
MDW1:55 pmChicago Midway
Jan 19
MDW8:30 amChicago Midway
4h 25m
PDX10:55 amPortland

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 May is, on average, the cheapest month to fly to Chicago Midway Airport from Portland, with most prices found around $267. If you are unable to visit Chicago Midway Airport during the month of May, then departing from Portland during the month July is also very affordable. Most momondo users find prices during this month for around $282.

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

According to our data, Wednesday is the cheapest day to fly to Chicago Midway Airport from Portland. The lowest ticket price found for a Wednesday departure recently was $285. 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 $559.

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 $318 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $455. 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.

Can stopping save me money on Portland to Chicago Midway Airport flights?

You could potentially save up to 40% 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

$59

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 $59. The best round-trip flight deal from Portland to Chicago Midway Airport found on momondo in the last 72 hours is $108.
The fastest flight from Portland to Chicago Midway Airport takes 3h 55m
Direct flights go from Portland to Chicago Midway Airport every day.

  • 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 $134Free CancellationRating
6.1
3,472 reviews
Search Frontier flights
DeltaPriceFrom $216Free CancellationRating
8.0
8,594 reviews
Search Delta flights
SouthwestPriceFrom $233Free CancellationRating
8.1
4,804 reviews
Search Southwest flights
  • Southwest Flights From Portland to Chicago Midway Airport

    Southwest operates around 9 flights from Portland to Chicago Midway Airport every week. The average price of these flights found in the last 72 hours has been $551, but momondo users have found Southwest deals from Portland to Chicago Midway Airport from as low as $233 round-trip. Southwest has been scored 8.1/10 in 4,804 reviews.


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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