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Cheap flights from Chicago Midway Airport to Portland from $103

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Portland departing on 11/24. 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 Chicago Midway Airport to Portland

Cheap round-trip flights

Frontier Logo
6:24 pm - 11:48 amMDW-PDX
19h 24m1 stop
Frontier Logo
12:43 pm - 12:36 amPDX-MDW
9h 53m1 stop
$204Frontier
Find Deal
Fri, Oct 10 - Sun, Oct 12
Southwest Logo
8:45 am - 3:20 pmMDW-PDX
8h 35m1 stop
Southwest Logo
5:30 am - 7:45 pmPDX-MDW
12h 15m2 stops
$205Southwest
Find Deal
Wed, Nov 12 - Sun, Nov 16
Southwest Logo
6:25 pm - 12:15 amMDW-PDX
7h 50m2 stops
Southwest Logo
5:30 am - 7:45 pmPDX-MDW
12h 15m2 stops
$210Southwest
Find Deal
Thu, Nov 13 - Sun, Nov 16
Southwest Logo
9:50 pm - 12:20 amMDW-PDX
4h 30mnonstop
Southwest Logo
7:40 pm - 5:05 amPDX-MDW
7h 25m1 stop
$213Southwest
Find Deal
Thu, Nov 13 - Sat, Nov 22
Frontier Logo
6:24 pm - 11:48 amMDW-PDX
19h 24m1 stop
Frontier Logo
12:43 pm - 12:36 amPDX-MDW
9h 53m1 stop
$218Frontier
Find Deal
Thu, Oct 16 - Sun, Oct 19
Southwest Logo
3:45 pm - 6:05 pmMDW-PDX
4h 20mnonstop
Southwest Logo
6:00 am - 6:05 pmPDX-MDW
10h 05m1 stop
$224Southwest
Find Deal
Sat, Oct 25 - Fri, Oct 31
Southwest Logo
8:00 pm - 1:05 amMDW-PDX
7h 05m1 stop
Southwest Logo
7:00 pm - 5:05 amPDX-MDW
8h 05m1 stop
$228Southwest
Find Deal
Sat, Nov 22 - Mon, Nov 24
Delta Logo
3:00 pm - 8:26 pmMDW-PDX
7h 26m1 stop
Delta Logo
11:26 am - 10:14 pmPDX-MDW
8h 48m1 stop
$229Delta
Find Deal
Sat, Oct 25 - Fri, Oct 31
Delta Logo
1:48 pm - 8:26 pmMDW-PDX
8h 38m1 stop
Delta Logo
12:40 am - 8:55 amPDX-MDW
6h 15m1 stop
$251Delta
Find Deal
Tue, Oct 21 - Tue, Oct 28
Delta Logo
3:00 pm - 8:26 pmMDW-PDX
7h 26m1 stop
Delta Logo
12:40 am - 8:55 amPDX-MDW
6h 15m1 stop
$264Delta
Find Deal
Sat, Oct 25 - Sat, Oct 25

Southwest flights from Chicago Midway Airport to Portland

Our best Southwest deals on Chicago Midway Airport to Portland flight tickets
Southwest
Nov 12
MDW8:45 amChicago Midway
8h 35m
1 stop
PDX3:20 pmPortland
Nov 16
PDX5:30 amPortland
12h 15m
2 stops
MDW7:45 pmChicago Midway
$205
Find similar
Southwest
Nov 13
MDW6:25 pmChicago Midway
7h 50m
2 stops
PDX12:15 amPortland
Nov 16
PDX5:30 amPortland
12h 15m
2 stops
MDW7:45 pmChicago Midway
$210
Find similar
Southwest
Nov 13
MDW9:50 pmChicago Midway
4h 30m
PDX12:20 amPortland
Nov 22
PDX7:40 pmPortland
7h 25m
1 stop
MDW5:05 amChicago Midway
$213
Find similar

Frontier flights from Chicago Midway Airport to Portland

Our best Frontier deals on Chicago Midway Airport to Portland flight tickets
Frontier
Oct 10
MDW6:24 pmChicago Midway
19h 24m
1 stop
PDX11:48 amPortland
Oct 12
PDX12:43 pmPortland
9h 53m
1 stop
MDW12:36 amChicago Midway
$204
Find similar
Frontier
Oct 16
MDW6:24 pmChicago Midway
19h 24m
1 stop
PDX11:48 amPortland
Oct 19
PDX12:43 pmPortland
9h 53m
1 stop
MDW12:36 amChicago Midway
$218
Find similar
Frontier
Sep 26
MDW4:48 pmChicago Midway
9h 24m
1 stop
PDX12:12 amPortland
Oct 23
PDX12:43 pmPortland
9h 53m
1 stop
MDW12:36 amChicago Midway
$234
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Portland 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 September 17, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Portland that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Fri 10/10

6:24 pm-11:48 am

1 stop19h 24m

Portland

Sun 10/12

12:43 pm-12:36 am

1 stop9h 53m

$204

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Wed 11/12

8:45 am-3:20 pm

1 stop8h 35m

Portland

Sun 11/16

5:30 am-7:45 pm

2 stops12h 15m

$205

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Thu 11/13

6:25 pm-12:15 am

2 stops7h 50m

Portland

Sun 11/16

5:30 am-7:45 pm

2 stops12h 15m

$210

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Thu 11/13

9:50 pm-12:20 am

Nonstop4h 30m

Portland

Sat 11/22

7:40 pm-5:05 am

1 stop7h 25m

$213

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Thu 10/16

6:24 pm-11:48 am

1 stop19h 24m

Portland

Sun 10/19

12:43 pm-12:36 am

1 stop9h 53m

$218

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Sat 10/25

3:45 pm-6:05 pm

Nonstop4h 20m

Portland

Fri 10/31

6:00 am-6:05 pm

1 stop10h 05m

$224

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Sat 11/22

8:00 pm-1:05 am

1 stop7h 05m

Portland

Mon 11/24

7:00 pm-5:05 am

1 stop8h 05m

$228

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Sat 10/25

3:00 pm-8:26 pm

1 stop7h 26m

Portland

Fri 10/31

11:26 am-10:14 pm

1 stop8h 48m

$229

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Tue 10/21

1:48 pm-8:26 pm

1 stop8h 38m

Portland

Tue 10/28

12:40 am-8:55 am

1 stop6h 15m

$251

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Sat 10/25

3:00 pm-8:26 pm

1 stop7h 26m

Portland

Sat 10/25

12:40 am-8:55 am

1 stop6h 15m

$264

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 Portland from

How to get the cheapest flight ticket from Chicago Midway Airport to Portland

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 Portland?

The cheapest month to fly to Portland from Chicago Midway Airport is in January. Flight prices, which tend to average around $254, are often lower during this time because this is during the off-season. If you don’t want to visit Portland in January, then you should wait until February to fly from Chicago Midway Airport, when ticket prices are also cheap, with an average price of $288.

What is the cheapest day to depart on your flight to Portland?

The cheapest day to depart on your flight to Portland is on a Wednesday when prices can be found for as low as $330. This is often the case because there is less demand to fly during this day of the week. The most expensive day to fly to Portland is Monday, with ticket prices averaging around $406.

What is the cheapest time of day to depart on your flight to Portland?

The cheapest time of day to fly to Portland is in the evening when flights can be purchased for as low as $326. At noon is when there is more demand to fly to Portland, so prices are often more expensive at around $449 per ticket.

What is the cheapest Chicago Midway to Portland flight route?

Fly from Chicago Midway to Portland for the best Chicago Midway - Portland flight prices

What cabin class options are available on Chicago Midway to Portland flights?

There is only 1 cabin class available to choose from on Chicago Midway to Portland 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 Chicago Midway Airport to Portland flights?

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

When to book flights from Chicago Midway Airport to Portland

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to Portland according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago Midway Airport to Portland (MDW to PDX) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Portland

Best Price Found

$89

Fastest flight time

4h 15m

Direct flights

Every day

Airports in Portland

1 airport
The best one-way flight to Portland from Chicago Midway Airport in the past 72 hours is $89. The best round-trip flight deal from Chicago Midway Airport to Portland found on momondo in the last 72 hours is $249.
The fastest flight from Chicago Midway Airport to Portland takes 4h 15m
Direct flights go from Chicago Midway Airport to Portland every day.
There is 1 airport near Portland: Portland (PDX)
Search flight deals

  • How far is Chicago Midway to Portland by plane?

    The distance between Chicago Midway and Portland is about 1749.8 mi. A reasonable flight in good conditions will take 4h 20m.

  • When did momondo last update prices for flights from Chicago Midway Airport to Portland Airport?

    Prices for flights from Chicago Midway Airport to Portland Airport are refreshed on a daily basis.

  • How many operators does momondo search for flights from Chicago Midway Airport to Portland Airport?

  • How old do you have to be to fly from Chicago Midway Airport to Portland Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago Midway Airport to Portland Airport.

  • What documentation or ID do you need to fly to Portland Airport?

    The necessary travel and health documents for your Portland Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Chicago Midway Airport to Portland?

  • What is the most popular airline from Chicago Midway Airport to Portland?

Best airlines flying from Chicago Midway Airport to Portland

Compare and see reviews for airlines that fly from Chicago Midway Airport to Portland with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $108Free CancellationRating
5.8
3,173 reviews
Search Frontier flights
SouthwestPriceFrom $238Free CancellationRating
8.0
4,242 reviews
Search Southwest flights

  • Southwest Flights From Chicago Midway Airport to Portland

    Southwest is one of the most popular airlines flying from Chicago Midway Airport to Portland, operating 15 flights/week on average for this route. A good Southwest flight deal for Chicago Midway Airport to Portland starts from $238 round-trip, up to an average price of $453. Our users have rated Southwest at 8.0/10.

Traveling to a place near Portland?

Book flights to Portland if you plan to visit one of these locations
Lincoln City
Seaside
Cannon Beach
Vancouver
Salem
Astoria
Long Beach
Depoe Bay
Rockaway Beach
Beaverton
Hillsboro
Hood River
Gresham
McMinnville
Longview
Tigard
The Dalles
Pacific City
Tillamook
Manzanita

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Portland?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Portland from Chicago.

Can I find flights from Chicago to Portland with flexible booking policies on momondo?

Flights from Chicago to Portland 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 Chicago to Portland?

momondo provides multiple filters to help you find the best flight to Portland from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Chicago to Portland right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Chicago to Portland now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Portland and let you know when they change.

An easier way to manage your Portland trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
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