Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Chicago Midway Airport to Portland from $153

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 6/3. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

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
4:40 pm - 7:00 pm
MDW
-
PDX
4h 20mnonstop
Southwest Logo
11:30 pm - 5:20 am
PDX
-
MDW
3h 50mnonstop
$310Southwest
Fri, Jul 3 - Tue, Jul 7
Southwest Logo
8:25 pm - 10:45 pm
MDW
-
PDX
4h 20mnonstop
Southwest Logo
11:30 pm - 5:20 am
PDX
-
MDW
3h 50mnonstop
$315Southwest
Sat, Jun 13 - Sat, Jun 20
Southwest Logo
9:35 pm - 11:55 pm
MDW
-
PDX
4h 20mnonstop
Southwest Logo
7:50 pm - 5:45 am
PDX
-
MDW
7h 55m
1 stop
$320Southwest
Fri, Jul 3 - Tue, Jul 7
Southwest Logo
9:50 pm - 12:10 am
MDW
-
PDX
4h 20mnonstop
Southwest Logo
5:40 am - 11:35 am
PDX
-
MDW
3h 55mnonstop
$321Southwest
Fri, May 29 - Tue, Jun 2
Southwest Logo
6:00 pm - 8:15 pm
MDW
-
PDX
4h 15mnonstop
Southwest Logo
11:30 pm - 5:25 am
PDX
-
MDW
3h 55mnonstop
$325Southwest
Sat, Aug 8 - Wed, Aug 12
Southwest Logo
9:35 pm - 11:55 pm
MDW
-
PDX
4h 20mnonstop
Southwest Logo
11:30 pm - 5:20 am
PDX
-
MDW
3h 50mnonstop
$326Southwest
Fri, Jul 24 - Wed, Jul 29
Southwest Logo
2:35 pm - 7:40 pm
MDW
-
PDX
7h 05m
1 stop
Southwest Logo
11:30 pm - 5:20 am
PDX
-
MDW
3h 50mnonstop
$330Southwest
Sat, Jun 27 - Fri, Jul 3
Southwest Logo
7:40 pm - 12:55 am
MDW
-
PDX
7h 15m
1 stop
Southwest Logo
11:55 pm - 5:50 am
PDX
-
MDW
3h 55mnonstop
$331Southwest
Fri, May 29 - Tue, Jun 2
Delta Logo
1:52 pm - 8:17 pm
MDW
-
PDX
8h 25m
1 stop
Delta Logo
12:32 am - 8:40 am
PDX
-
MDW
6h 08m
1 stop
$335Delta
Sat, Aug 8 - Fri, Aug 14
Southwest Logo
6:40 am - 10:50 am
MDW
-
PDX
6h 10m
1 stop
Southwest Logo
11:30 pm - 5:25 am
PDX
-
MDW
3h 55mnonstop
$336Southwest
Wed, Aug 19 - Sun, Aug 23

Southwest flights from Chicago Midway Airport to Portland

Our best Southwest deals on Chicago Midway Airport to Portland flight tickets
Southwest
Jul 3
MDW4:40 pmChicago Midway
4h 20m
PDX7:00 pmPortland
Jul 7
PDX11:30 pmPortland
3h 50m
MDW5:20 amChicago Midway
$310
Southwest
Jun 13
MDW8:25 pmChicago Midway
4h 20m
PDX10:45 pmPortland
Jun 20
PDX11:30 pmPortland
3h 50m
MDW5:20 amChicago Midway
$315
Southwest
Jul 3
MDW9:35 pmChicago Midway
4h 20m
PDX11:55 pmPortland
Jul 7
PDX7:50 pmPortland
7h 55m
1 stop
MDW5:45 amChicago Midway
$320

Delta flights from Chicago Midway Airport to Portland

Our best Delta deals on Chicago Midway Airport to Portland flight tickets
Delta
Aug 8
MDW1:52 pmChicago Midway
8h 25m
1 stop
PDX8:17 pmPortland
Aug 14
PDX12:32 amPortland
6h 08m
1 stop
MDW8:40 amChicago Midway
$335
Delta
May 27
MDW12:53 pmChicago Midway
7h 45m
1 stop
PDX6:38 pmPortland
Jun 2
PDX9:39 pmPortland
10h 21m
1 stop
MDW10:00 amChicago Midway
$341
Delta
Jul 10
MDW7:06 pmChicago Midway
6h 12m
1 stop
PDX11:18 pmPortland
Jul 13
PDX11:15 pmPortland
7h 53m
1 stop
MDW9:08 amChicago Midway
$357

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 May 15, 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

Cheapest round-trip
Quickest round-trip

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Fri 7/3

4:40 pm-7:00 pm

Nonstop4h 20m

Portland

Tue 7/7

11:30 pm-5:20 am

Nonstop3h 50m

$310

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Sat 6/13

8:25 pm-10:45 pm

Nonstop4h 20m

Portland

Sat 6/20

11:30 pm-5:20 am

Nonstop3h 50m

$315

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Fri 7/3

9:35 pm-11:55 pm

Nonstop4h 20m

Portland

Tue 7/7

7:50 pm-5:45 am

1 stop7h 55m

$320

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Fri 5/29

9:50 pm-12:10 am

Nonstop4h 20m

Portland

Tue 6/2

5:40 am-11:35 am

Nonstop3h 55m

$321

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Sat 8/8

6:00 pm-8:15 pm

Nonstop4h 15m

Portland

Wed 8/12

11:30 pm-5:25 am

Nonstop3h 55m

$325

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Fri 7/24

9:35 pm-11:55 pm

Nonstop4h 20m

Portland

Wed 7/29

11:30 pm-5:20 am

Nonstop3h 50m

$326

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Sat 6/27

2:35 pm-7:40 pm

1 stop7h 05m

Portland

Fri 7/3

11:30 pm-5:20 am

Nonstop3h 50m

$330

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Fri 5/29

7:40 pm-12:55 am

1 stop7h 15m

Portland

Tue 6/2

11:55 pm-5:50 am

Nonstop3h 55m

$331

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Sat 8/8

1:52 pm-8:17 pm

1 stop8h 25m

Portland

Fri 8/14

12:32 am-8:40 am

1 stop6h 08m

$335

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Wed 8/19

6:40 am-10:50 am

1 stop6h 10m

Portland

Sun 8/23

11:30 pm-5:25 am

Nonstop3h 55m

$336

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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?

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 August to fly from Chicago Midway Airport, when ticket prices are also cheap, with an average price of $285.

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 $324. 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 $387.

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 $322. At noon is when there is more demand to fly to Portland, so prices are often more expensive at around $464 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

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

You could potentially save up to 27% on your flight if you consider stops on a Chicago Midway Airport to Portland flight.

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

As of May 2026, prices for Chicago Midway Airport to Portland flights are approximately 66% cheaper 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

$163

Fastest flight time

4h 10m

Direct flights

Tue, Wed, Thu, Fri, Sat and Sun

Airports in Portland

1 airport
The best one-way flight to Portland from Chicago Midway Airport in the past 72 hours is $163. The best round-trip flight deal from Chicago Midway Airport to Portland found on momondo in the last 72 hours is $305.
The fastest flight from Chicago Midway Airport to Portland takes 4h 10m
Direct flights go from Chicago Midway Airport to Portland on Tuesday, Wednesday, Thursday, Friday, Saturday and Sunday. The only airline offering direct flights is Southwest.
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 10m.

  • 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 $227Free CancellationRating
8.0
4,299 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 12 flights/week on average for this route. A good Southwest flight deal for Chicago Midway Airport to Portland starts from $227 round-trip, up to an average price of $358. 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
Rockaway Beach
Beaverton
Depoe Bay
Hillsboro
Tigard
Longview
Hood River
Troutdale
Newberg
The Dalles
Gresham
McMinnville
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.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Sun 6/14
Sun 6/21
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the United States