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Cheap flights from Chicago Midway Airport to Portland from $179

1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Chicago Midway Airport to Portland

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
1:20 pm - 9:50 pmMDW  Chicago Midway-PDX Portland
10h 30m2 stops Louisville Intl Las Vegas Harry Reid Intl
Southwest Logo
1:10 pm - 8:50 pmPDX  Portland-MDW Chicago Midway
5h 40m1 stop Denver Intl
$359Southwest
Wed, Dec 2 - Sat, Dec 5
Southwest Logo
6:05 am - 10:40 amMDW  Chicago Midway-PDX Portland
6h 35m1 stop Denver Intl
Southwest Logo
6:20 am - 5:05 pmPDX  Portland-MDW Chicago Midway
8h 45m2 stops Denver Intl Birmingham
$359Southwest
Wed, Dec 2 - Mon, Dec 7
Delta Logo
9:38 am - 6:58 pmMDW  Chicago Midway-PDX Portland
11h 20m2 stops Detroit Metropolitan Wayne County Seattle/Tacoma Intl
Delta Logo
12:47 pm - 11:55 pmPDX  Portland-MDW Chicago Midway
9h 08m1 stop Atlanta Hartsfield-Jackson
$359Delta
Thu, Jan 21 - Sun, Jan 24
Delta Logo
9:38 am - 6:58 pmMDW  Chicago Midway-PDX Portland
11h 20m2 stops Detroit Metropolitan Wayne County Seattle/Tacoma Intl
Delta Logo
6:20 am - 4:53 pmPDX  Portland-MDW Chicago Midway
8h 33m1 stop Minneapolis St Paul
$359Delta
Fri, Feb 5 - Sun, Feb 7
Southwest Logo
5:20 am - 1:05 pmMDW  Chicago Midway-PDX Portland
9h 45m2 stops Phoenix Sky Harbor Intl Sacramento Intl
Southwest Logo
2:50 pm - 12:05 amPDX  Portland-MDW Chicago Midway
7h 15m1 stop Denver Intl
$359Southwest
Thu, Jan 28 - Sun, Jan 31
Southwest Logo
10:15 am - 6:05 pmMDW  Chicago Midway-PDX Portland
9h 50m2 stops Oklahoma City Will Rogers World Denver Intl
Southwest Logo
4:25 pm - 4:25 amPDX  Portland-MDW Chicago Midway
10h 00m1 stop San Diego
$359Southwest
Wed, Dec 16 - Sun, Dec 20
Southwest Logo
10:10 am - 7:45 pmMDW  Chicago Midway-PDX Portland
11h 35m1 stop San Diego
Southwest Logo
2:50 pm - 12:05 amPDX  Portland-MDW Chicago Midway
7h 15m1 stop Denver Intl
$359Southwest
Fri, Feb 5 - Sun, Feb 7
Delta Logo
6:00 am - 4:28 pmMDW  Chicago Midway-PDX Portland
12h 28m2 stops Atlanta Hartsfield-Jackson Salt Lake City
Delta Logo
6:20 am - 4:53 pmPDX  Portland-MDW Chicago Midway
8h 33m1 stop Minneapolis St Paul
$359Delta
Wed, Jan 20 - Sun, Jan 24
Southwest Logo
5:20 pm - 10:45 pmMDW  Chicago Midway-PDX Portland
7h 25m2 stops Omaha Eppley Airfield Denver Intl
Southwest Logo
7:35 am - 5:35 pmPDX  Portland-MDW Chicago Midway
8h 00m2 stops Phoenix Sky Harbor Intl Wichita Eisenhower National
$360Southwest
Fri, Dec 11 - Sun, Dec 13
Southwest Logo
1:20 pm - 10:20 pmMDW  Chicago Midway-PDX Portland
11h 00m2 stops Detroit Metropolitan Wayne County Denver Intl
Southwest Logo
7:35 am - 5:35 pmPDX  Portland-MDW Chicago Midway
8h 00m2 stops Phoenix Sky Harbor Intl Wichita Eisenhower National
$360Southwest
Fri, Dec 4 - Sun, Dec 6

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Southwest flights from Chicago Midway Airport to Portland

Our best Southwest deals on Chicago Midway Airport to Portland flight tickets
Southwest
Dec 2
MDW1:20 pmChicago Midway
10h 30m
2 stops
PDX9:50 pmPortland
Dec 5
PDX1:10 pmPortland
5h 40m
1 stop
MDW8:50 pmChicago Midway
$359
Southwest
Dec 4
MDW1:20 pmChicago Midway
11h 00m
2 stops
PDX10:20 pmPortland
Dec 6
PDX7:35 amPortland
8h 00m
2 stops
MDW5:35 pmChicago Midway
$360
Southwest
Dec 20
MDW9:30 pmChicago Midway
4h 45m
PDX12:15 amPortland
Jan 4
PDX11:30 pmPortland
3h 45m
MDW5:15 amChicago Midway
$367

Delta flights from Chicago Midway Airport to Portland

Our best Delta deals on Chicago Midway Airport to Portland flight tickets
Delta
Nov 10
MDW9:30 amChicago Midway
8h 59m
2 stops
PDX4:29 pmPortland
Nov 14
PDX12:35 amPortland
6h 15m
1 stop
MDW8:50 amChicago Midway
$363
Delta
Jan 21
MDW9:30 amChicago Midway
11h 33m
2 stops
PDX7:03 pmPortland
Jan 24
PDX6:15 amPortland
8h 35m
1 stop
MDW4:50 pmChicago Midway
$364
Delta
Nov 13
MDW1:05 pmChicago Midway
8h 09m
1 stop
PDX7:14 pmPortland
Nov 14
PDX12:35 amPortland
6h 15m
1 stop
MDW8:50 amChicago Midway
$368

momondo Fare Finder

 
Use the filters below to find and compare flights from Chicago Midway Airport to Portland that are best for you.

Fly from

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Route

Depart

Return

Price

Cheapest round-trip

ChicagoPortland

MDW Chicago Midway - PDX Portland

MDWPDX

Chicago Midway

Wed 12/2

1:20 pm-9:50 pm

2 stops10h 30m

Portland

Sat 12/5

1:10 pm-8:50 pm

1 stop5h 40m

$359
Quickest round-trip

ChicagoPortland

MDW Chicago Midway - PDX Portland

MDWPDX

Chicago Midway

Wed 12/2

6:05 am-10:40 am

1 stop6h 35m

Portland

Mon 12/7

6:20 am-5:05 pm

2 stops8h 45m

$359

ChicagoPortland

MDW Chicago Midway - PDX Portland

MDWPDX

Chicago Midway

Thu 1/21

9:38 am-6:58 pm

2 stops11h 20m

Portland

Sun 1/24

12:47 pm-11:55 pm

1 stop9h 08m

$359

ChicagoPortland

MDW Chicago Midway - PDX Portland

MDWPDX

Chicago Midway

Fri 2/5

9:38 am-6:58 pm

2 stops11h 20m

Portland

Sun 2/7

6:20 am-4:53 pm

1 stop8h 33m

$359

ChicagoPortland

MDW Chicago Midway - PDX Portland

MDWPDX

Chicago Midway

Thu 1/28

5:20 am-1:05 pm

2 stops9h 45m

Portland

Sun 1/31

2:50 pm-12:05 am

1 stop7h 15m

$359

ChicagoPortland

MDW Chicago Midway - PDX Portland

MDWPDX

Chicago Midway

Wed 12/16

10:15 am-6:05 pm

2 stops9h 50m

Portland

Sun 12/20

4:25 pm-4:25 am

1 stop10h 00m

$359

ChicagoPortland

MDW Chicago Midway - PDX Portland

MDWPDX

Chicago Midway

Fri 2/5

10:10 am-7:45 pm

1 stop11h 35m

Portland

Sun 2/7

2:50 pm-12:05 am

1 stop7h 15m

$359

ChicagoPortland

MDW Chicago Midway - PDX Portland

MDWPDX

Chicago Midway

Wed 1/20

6:00 am-4:28 pm

2 stops12h 28m

Portland

Sun 1/24

6:20 am-4:53 pm

1 stop8h 33m

$359

ChicagoPortland

MDW Chicago Midway - PDX Portland

MDWPDX

Chicago Midway

Fri 12/11

5:20 pm-10:45 pm

2 stops7h 25m

Portland

Sun 12/13

7:35 am-5:35 pm

2 stops8h 00m

$360

ChicagoPortland

MDW Chicago Midway - PDX Portland

MDWPDX

Chicago Midway

Fri 12/4

1:20 pm-10:20 pm

2 stops11h 00m

Portland

Sun 12/6

7:35 am-5:35 pm

2 stops8h 00m

$360

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 typical price of a round-trip flight between Chicago Midway Airport and Portland?

Prices are currently low for flights on this route.

Typical prices usually range from $360 to $371.
The lowest price recently found on this route was $359.

What is the cheapest month to fly to Portland?

The cheapest month to fly to Portland from Chicago Midway Airport is in March. Flight prices, which tend to average around $227, are often lower during this time because this is during the off-season. If you don’t want to visit Portland in March, then you should wait until September to fly from Chicago Midway Airport, when ticket prices are also cheap, with an average price of $338.

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 Tuesday when prices can be found for as low as $360. 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 Sunday, with ticket prices averaging around $447.

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 $350. At noon is when there is more demand to fly to Portland, so prices are often more expensive at around $461 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 Airport to Portland flights?

There is only 1 cabin class available to choose from on Chicago Midway Airport to Portland flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

How have Chicago Midway Airport to Portland flight prices changed over time?

As of October 2026, prices for Chicago Midway Airport to Portland flights are approximately 115% more expensive when compared to flights at the same time last year.

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

$179

Fastest flight time

4h 25m

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 $179. The best round-trip flight deal from Chicago Midway Airport to Portland found on momondo in the last 72 hours is $359.
The fastest flight from Chicago Midway Airport to Portland takes 4h 25m
Direct flights go from Chicago Midway Airport to Portland every day.
There is 1 airport in Portland. From Chicago Midway Airport there are direct flights to Portland (PDX).
Search flight deals

Frequently asked questions about flying from Chicago Midway Airport to Portland

  • 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 25m.

  • 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
SouthwestPriceFrom $239Free CancellationRating
7.9
4,219 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 9 flights/week on average for this route. A good Southwest flight deal for Chicago Midway Airport to Portland starts from $239 round-trip, up to an average price of $374. Our users have rated Southwest at 7.9/10.

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
Beaverton
Long Beach
Rockaway Beach
Hillsboro
Tigard
Longview
Hood River
Newberg
Clackamas
Gresham
Troutdale
Wilsonville
Depoe Bay
McMinnville

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.

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