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Cheap flights from Chicago Midway Airport to Portland from $109

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 3/24. 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

Enter your travel dates to find the best prices.
Southwest Logo
6:05 pm - 8:25 pm
MDW
-
PDX
4h 20mnonstop
Southwest Logo
11:55 pm - 5:50 am
PDX
-
MDW
3h 55mnonstop
$207Southwest
Sat, May 2 - Sat, May 9
Southwest Logo
8:30 pm - 11:00 pm
MDW
-
PDX
4h 30mnonstop
Southwest Logo
7:25 am - 5:15 pm
PDX
-
MDW
7h 50m
1 stop
$208Southwest
Sat, Feb 28 - Wed, Mar 4
Southwest Logo
8:10 pm - 1:40 am
MDW
-
PDX
7h 30m
1 stop
Southwest Logo
6:20 pm - 5:55 am
PDX
-
MDW
9h 35m
1 stop
$211Southwest
Sat, Mar 7 - Sat, Mar 14
Southwest Logo
8:10 am - 10:45 am
MDW
-
PDX
4h 35mnonstop
Southwest Logo
5:20 am - 11:15 am
PDX
-
MDW
3h 55mnonstop
$217Southwest
Mon, Mar 2 - Fri, Mar 6
Southwest Logo
10:30 pm - 12:55 am
MDW
-
PDX
4h 25mnonstop
Southwest Logo
11:55 pm - 5:45 am
PDX
-
MDW
3h 50mnonstop
$221Southwest
Sat, Mar 7 - Sat, Mar 14
Southwest Logo
8:30 pm - 11:00 pm
MDW
-
PDX
4h 30mnonstop
Southwest Logo
6:30 am - 12:25 pm
PDX
-
MDW
3h 55mnonstop
$224Southwest
Sat, Feb 28 - Wed, Mar 4
Southwest Logo
10:30 pm - 12:55 am
MDW
-
PDX
4h 25mnonstop
Southwest Logo
7:15 pm - 5:00 am
PDX
-
MDW
7h 45m
1 stop
$225Southwest
Sat, Mar 21 - Fri, Mar 27
Southwest Logo
8:10 am - 10:45 am
MDW
-
PDX
4h 35mnonstop
Southwest Logo
8:55 pm - 5:45 am
PDX
-
MDW
6h 50m
1 stop
$227Southwest
Mon, Mar 2 - Thu, Mar 5
Southwest Logo
9:50 pm - 12:10 am
MDW
-
PDX
4h 20mnonstop
Southwest Logo
11:55 pm - 5:50 am
PDX
-
MDW
3h 55mnonstop
$231Southwest
Mon, May 18 - Sat, May 23
Southwest Logo
5:35 pm - 11:00 pm
MDW
-
PDX
7h 25m
1 stop
Southwest Logo
7:05 pm - 5:40 am
PDX
-
MDW
8h 35m
1 stop
$232Southwest
Tue, Apr 7 - Sat, Apr 11

Southwest flights from Chicago Midway Airport to Portland

Our best Southwest deals on Chicago Midway Airport to Portland flight tickets
Southwest
May 2
MDW6:05 pmChicago Midway
4h 20m
PDX8:25 pmPortland
May 9
PDX11:55 pmPortland
3h 55m
MDW5:50 amChicago Midway
$207
Southwest
Feb 28
MDW8:30 pmChicago Midway
4h 30m
PDX11:00 pmPortland
Mar 4
PDX7:25 amPortland
7h 50m
1 stop
MDW5:15 pmChicago Midway
$208
Southwest
Mar 7
MDW8:10 pmChicago Midway
7h 30m
1 stop
PDX1:40 amPortland
Mar 14
PDX6:20 pmPortland
9h 35m
1 stop
MDW5:55 amChicago Midway
$211

Delta flights from Chicago Midway Airport to Portland

Our best Delta deals on Chicago Midway Airport to Portland flight tickets
Delta
Apr 11
MDW2:05 pmChicago Midway
8h 20m
1 stop
PDX8:25 pmPortland
Apr 18
PDX6:00 amPortland
5h 32m
1 stop
MDW1:32 pmChicago Midway
$238
Delta
Mar 2
MDW1:49 pmChicago Midway
8h 41m
1 stop
PDX8:30 pmPortland
Mar 9
PDX10:30 pmPortland
9h 26m
1 stop
MDW9:56 amChicago Midway
$247
Delta
May 4
MDW2:12 pmChicago Midway
7h 53m
1 stop
PDX8:05 pmPortland
May 4
PDX12:30 amPortland
6h 21m
1 stop
MDW8:51 amChicago Midway
$258

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 February 11, 2026.
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

Sat 5/2

6:05 pm-8:25 pm

Nonstop4h 20m

Portland

Sat 5/9

11:55 pm-5:50 am

Nonstop3h 55m

$207

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Sat 2/28

8:30 pm-11:00 pm

Nonstop4h 30m

Portland

Wed 3/4

7:25 am-5:15 pm

1 stop7h 50m

$208

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Sat 3/7

8:10 pm-1:40 am

1 stop7h 30m

Portland

Sat 3/14

6:20 pm-5:55 am

1 stop9h 35m

$211

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Mon 3/2

8:10 am-10:45 am

Nonstop4h 35m

Portland

Fri 3/6

5:20 am-11:15 am

Nonstop3h 55m

$217

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Sat 3/7

10:30 pm-12:55 am

Nonstop4h 25m

Portland

Sat 3/14

11:55 pm-5:45 am

Nonstop3h 50m

$221

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Sat 2/28

8:30 pm-11:00 pm

Nonstop4h 30m

Portland

Wed 3/4

6:30 am-12:25 pm

Nonstop3h 55m

$224

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Sat 3/21

10:30 pm-12:55 am

Nonstop4h 25m

Portland

Fri 3/27

7:15 pm-5:00 am

1 stop7h 45m

$225

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Mon 3/2

8:10 am-10:45 am

Nonstop4h 35m

Portland

Thu 3/5

8:55 pm-5:45 am

1 stop6h 50m

$227

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Mon 5/18

9:50 pm-12:10 am

Nonstop4h 20m

Portland

Sat 5/23

11:55 pm-5:50 am

Nonstop3h 55m

$231

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Tue 4/7

5:35 pm-11:00 pm

1 stop7h 25m

Portland

Sat 4/11

7:05 pm-5:40 am

1 stop8h 35m

$232

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 December. Flight prices, which tend to average around $313, are often lower during this time because this is during the off-season. If you don’t want to visit Portland in December, then you should wait until February to fly from Chicago Midway Airport, when ticket prices are also cheap, with an average price of $350.

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 $380.

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 $312. At noon is when there is more demand to fly to Portland, so prices are often more expensive at around $447 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.

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

As of February 2026, prices for Chicago Midway Airport to Portland flights are approximately 228% 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

$108

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 $108. The best round-trip flight deal from Chicago Midway Airport to Portland found on momondo in the last 72 hours is $231.
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 in Portland. From Chicago Midway Airport there are direct flights to 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 15m.

  • 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 $234Free CancellationRating
8.0
4,280 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 4 flights/week on average for this route. A good Southwest flight deal for Chicago Midway Airport to Portland starts from $234 round-trip, up to an average price of $413. 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
Tigard
Longview
McMinnville
Gresham
Pacific City
The Dalles
Manzanita
Newberg

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

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