Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Chicago Midway Airport to Portland from $90

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 8/30. 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

Discover deals from 900+ travel sites with momondo.

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

Southwest Logo
2:10 pm - 4:25 pmMDW-PDX
4h 15mnonstop
Southwest Logo
6:55 am - 12:55 pmPDX-MDW
4h 00mnonstop
$179Southwest
Find Deal
Sat, Aug 30 - Sun, Aug 31
Southwest Logo
8:30 pm - 10:45 pmMDW-PDX
4h 15mnonstop
Southwest Logo
6:55 am - 12:55 pmPDX-MDW
4h 00mnonstop
$188Southwest
Find Deal
Tue, Aug 26 - Sun, Aug 31
Southwest Logo
11:40 am - 8:35 pmMDW-PDX
10h 55m1 stop
Southwest Logo
6:55 am - 12:55 pmPDX-MDW
4h 00mnonstop
$189Southwest
Find Deal
Sat, Aug 30 - Sun, Aug 31
Southwest Logo
3:45 pm - 6:05 pmMDW-PDX
4h 20mnonstop
Southwest Logo
1:25 pm - 7:20 pmPDX-MDW
3h 55mnonstop
$197Southwest
Find Deal
Sat, Oct 25 - Tue, Oct 28
Delta Logo
6:00 am - 12:59 pmMDW-PDX
8h 59m1 stop
Delta Logo
12:50 am - 8:55 amPDX-MDW
6h 05m1 stop
$208Delta
Find Deal
Sat, Oct 25 - Thu, Oct 30
Delta Logo
9:20 am - 3:51 pmMDW-PDX
8h 31m1 stop
Delta Logo
10:45 pm - 8:40 amPDX-MDW
7h 55m1 stop
$217Delta
Find Deal
Sat, Sep 13 - Sat, Sep 13
Delta Logo
6:00 am - 12:59 pmMDW-PDX
8h 59m1 stop
Delta Logo
11:36 am - 10:14 pmPDX-MDW
8h 38m1 stop
$223Delta
Find Deal
Sat, Oct 25 - Fri, Oct 31
Frontier Logo
12:35 pm - 12:15 amMDW-PDX
13h 40m1 stop
Frontier Logo
7:01 pm - 8:54 pmPDX-MDW
23h 53m1 stop
$257Frontier
Find Deal
Fri, Aug 15 - Sat, Aug 16
Frontier Logo
4:48 pm - 12:12 amMDW-PDX
9h 24m1 stop
Frontier Logo
10:27 am - 9:58 pmPDX-MDW
9h 31m1 stop
$258Frontier
Find Deal
Fri, Sep 5 - Sun, Sep 7
Frontier Logo
2:44 pm - 12:16 amMDW-PDX
11h 32m1 stop
Frontier Logo
6:35 am - 11:41 amPDX-MDW
27h 06m1 stop
$265Frontier
Find Deal
Thu, Aug 14 - Sun, Aug 17

Frontier flights from Chicago Midway Airport to Portland

Our best Frontier deals on Chicago Midway Airport to Portland flight tickets
Frontier
Aug 9
MDW2:44 pmChicago Midway
10h 40m
1 stop
PDX11:24 pmPortland
Aug 16
PDX6:35 amPortland
12h 19m
1 stop
MDW8:54 pmChicago Midway
$238
Find similar
Frontier
Aug 15
MDW12:35 pmChicago Midway
13h 40m
1 stop
PDX12:15 amPortland
Aug 16
PDX7:01 pmPortland
23h 53m
1 stop
MDW8:54 pmChicago Midway
$257
Find similar
Frontier
Sep 5
MDW4:48 pmChicago Midway
9h 24m
1 stop
PDX12:12 amPortland
Sep 7
PDX10:27 amPortland
9h 31m
1 stop
MDW9:58 pmChicago Midway
$258
Find similar

Southwest flights from Chicago Midway Airport to Portland

Our best Southwest deals on Chicago Midway Airport to Portland flight tickets
Southwest
Aug 30
MDW2:10 pmChicago Midway
4h 15m
PDX4:25 pmPortland
Aug 31
PDX6:55 amPortland
4h 00m
MDW12:55 pmChicago Midway
$179
Find similar
Southwest
Aug 26
MDW8:30 pmChicago Midway
4h 15m
PDX10:45 pmPortland
Aug 31
PDX6:55 amPortland
4h 00m
MDW12:55 pmChicago Midway
$188
Find similar
Southwest
Aug 30
MDW11:40 amChicago Midway
10h 55m
1 stop
PDX8:35 pmPortland
Aug 31
PDX6:55 amPortland
4h 00m
MDW12:55 pmChicago Midway
$189
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 July 31, 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

Sat 8/30

2:10 pm-4:25 pm

Nonstop4h 15m

Portland

Sun 8/31

6:55 am-12:55 pm

Nonstop4h 00m

$179

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Tue 8/26

8:30 pm-10:45 pm

Nonstop4h 15m

Portland

Sun 8/31

6:55 am-12:55 pm

Nonstop4h 00m

$188

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Sat 8/30

11:40 am-8:35 pm

1 stop10h 55m

Portland

Sun 8/31

6:55 am-12:55 pm

Nonstop4h 00m

$189

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Sat 10/25

3:45 pm-6:05 pm

Nonstop4h 20m

Portland

Tue 10/28

1:25 pm-7:20 pm

Nonstop3h 55m

$197

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Sat 10/25

6:00 am-12:59 pm

1 stop8h 59m

Portland

Thu 10/30

12:50 am-8:55 am

1 stop6h 05m

$208

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Sat 9/13

9:20 am-3:51 pm

1 stop8h 31m

Portland

Sat 9/13

10:45 pm-8:40 am

1 stop7h 55m

$217

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Sat 10/25

6:00 am-12:59 pm

1 stop8h 59m

Portland

Fri 10/31

11:36 am-10:14 pm

1 stop8h 38m

$223

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Fri 8/15

12:35 pm-12:15 am

1 stop13h 40m

Portland

Sat 8/16

7:01 pm-8:54 pm

1 stop23h 53m

$257

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Fri 9/5

4:48 pm-12:12 am

1 stop9h 24m

Portland

Sun 9/7

10:27 am-9:58 pm

1 stop9h 31m

$258

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Thu 8/14

2:44 pm-12:16 am

1 stop11h 32m

Portland

Sun 8/17

6:35 am-11:41 am

1 stop27h 06m

$265

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 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 $266, 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 $328. 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 $401.

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 $306. At noon is when there is more demand to fly to Portland, so prices are often more expensive at around $412 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 are 1 cabin classes 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

$90

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 $90. The best round-trip flight deal from Chicago Midway Airport to Portland found on momondo in the last 72 hours is $179.
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 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
FrontierPriceFrom $108Free CancellationRating
5.9
3,239 reviews
Search Frontier flights
SouthwestPriceFrom $238Free CancellationRating
8.0
4,246 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 $238 round-trip, up to an average price of $433. 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
Beaverton
Rockaway Beach
Hood River
Hillsboro
Gresham
McMinnville
Tigard
Longview
Pacific City
Manzanita
The Dalles
Tillamook

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
Tue 8/5
Tue 8/12
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the United States