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$82+ Cheap flights from Oregon to Midway (MDW)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/15. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — MDW
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheap flight deals from Oregon to Midway

Keep the following information in mind while searching for Oregon to Midway flight deals. Data was last updated September 15, 2025.

Round-trip from

$196
(Frontier)

One-way from

$82
(Southwest)

Popular in

March

Cheapest in

January

Average price

$303

Good round-trip deal

$312 or less

Good one-way deal

$198 or less
From Oregon to Chicago Midway
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One-way flight from Oregon to Chicago Midway
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Highest demand for flights based on searches. 8% potential increase in price ($33 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Oregon to Chicago Midway.
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Price to beat on a one-way flight from Oregon to Chicago Midway.
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Find flight deals from Oregon to Midway

Cheapest flights from Oregon to Midway
Explore the most affordable flight options available from Oregon to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2025.

This Frontier deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2312:43 pmPDX - MDW
1 stop9h 53mFrontier
Sun 10/269:26 pmMDW - PDX
2 stops16h 22mFrontier
Deal found 9/12$196
This Booking.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/2012:43 pmPDX - MDW
1 stop9h 41mFrontier
Thu 10/236:24 pmMDW - PDX
1 stop19h 24mFrontier
Deal found 9/13$198
This Frontier deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/17:15 amPDX - MDW
2 stops21h 56mFrontier
Fri 10/34:48 pmMDW - PDX
1 stop9h 24mFrontier
Deal found 9/14$204
This Kiwi.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/149:02 pmPDX - MDW
1 stop14h 55mFrontier
Mon 11/1712:30 pmMDW - PDX
1 stop25h 26mFrontier
Deal found 9/13$209
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/246:55 pmPDX - MDW
1 stop12h 20mSouthwest
Thu 1/18:45 amMDW - PDX
1 stop8h 35mSouthwest
Deal found 9/14$212
This Booking.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/3012:52 pmPDX - MDW
1 stop20h 38mFrontier
Sun 11/212:30 pmMDW - PDX
1 stop25h 26mFrontier
Deal found 9/14$219
This Frontier deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/266:05 amPDX - MDW
1 stop7h 48mFrontier
Mon 9/294:48 pmMDW - PDX
1 stop9h 24mFrontier
Deal found 9/13$226
This Kiwi.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1312:52 pmPDX - MDW
1 stop20h 38mFrontier
Mon 11/176:54 pmMDW - PDX
2 stops19h 02mFrontier
Deal found 9/13$227
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/316:00 amPDX - MDW
1 stop10h 05mSouthwest
Sun 11/29:50 pmMDW - PDX
Nonstop4h 30mSouthwest
Deal found 9/14$237
This Booking.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/612:52 pmPDX - MDW
1 stop20h 38mFrontier
Sun 11/912:30 pmMDW - PDX
1 stop25h 26mFrontier
Deal found 9/14$238
This Southwest deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/157:20 pmBOI - MDW
1 stop8h 55mSouthwest
Sat 10/185:00 amMDW - BOI
1 stop6h 55mSouthwest
Deal found 9/13$255
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/2411:39 pmBOI - MDW
1 stop9h 01mDelta
Mon 10/279:20 amMDW - BOI
1 stop5h 42mDelta
Deal found 9/14$262

Cheapflights Fare Finder

 
Customize your flight search to find flights from Oregon to Midway 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, Cheapflights users made 2,558,603 searches. Data last updated September 15, 2025.
Use the filters below to find and compare flights from Oregon to Chicago Midway Airport that are best for you.

Fly from

Oregon

Fly to

Midway

Route

Depart

Return

Price

BoiseChicago

BOI - MDW

BOIMDW

Boise Air Term. Gowen Fld

Wed 10/15

7:20 pm-5:15 am

1 stop8h 55m

Chicago Midway

Sat 10/18

5:00 am-10:55 am

1 stop6h 55m

$255

BoiseChicago

BOI - MDW

BOIMDW

Boise Air Term. Gowen Fld

Tue 10/28

3:15 pm-12:25 am

1 stop8h 10m

Chicago Midway

Wed 10/29

4:15 pm-11:05 pm

1 stop7h 50m

$255

PortlandChicago

PDX - MDW

PDXMDW

Portland

Fri 11/14

6:30 am-12:25 pm

Nonstop3h 55m

Chicago Midway

Mon 11/17

4:50 pm-7:20 pm

Nonstop4h 30m

$257

BoiseChicago

BOI - MDW

BOIMDW

Boise Air Term. Gowen Fld

Tue 11/4

5:42 am-1:08 pm

1 stop6h 26m

Chicago Midway

Wed 11/12

12:47 pm-12:35 am

2 stops12h 48m

$260

BoiseChicago

BOI - MDW

BOIMDW

Boise Air Term. Gowen Fld

Fri 10/24

11:39 pm-9:40 am

1 stop9h 01m

Chicago Midway

Mon 10/27

9:20 am-2:02 pm

1 stop5h 42m

$262

PortlandChicago

PDX - MDW

PDXMDW

Portland

Fri 10/17

10:58 pm-8:40 am

1 stop7h 42m

Chicago Midway

Sat 10/25

3:00 pm-8:26 pm

1 stop7h 26m

$264

PortlandChicago

PDX - MDW

PDXMDW

Portland

Tue 3/10

6:04 am-4:25 pm

1 stop8h 21m

Chicago Midway

Wed 3/11

9:20 am-4:51 pm

1 stop9h 31m

$267

PortlandChicago

PDX - MDW

PDXMDW

Portland

Fri 11/14

3:55 pm-12:05 am

1 stop6h 10m

Chicago Midway

Sun 11/16

9:50 pm-12:20 am

Nonstop4h 30m

$267

BoiseChicago

BOI - MDW

BOIMDW

Boise Air Term. Gowen Fld

Sat 11/22

8:40 pm-5:05 am

1 stop7h 25m

Chicago Midway

Sat 12/6

8:30 am-8:20 pm

2 stops12h 50m

$268

PortlandChicago

PDX - MDW

PDXMDW

Portland

Wed 2/11

12:55 am-8:54 am

1 stop5h 59m

Chicago Midway

Tue 2/17

9:20 am-4:51 pm

1 stop9h 31m

$270

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/12

Showing 1-10 of 60 results
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Best time to book a flight from Oregon to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Oregon with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Oregon to Chicago Midway Airport

What is the cheapest month to book a flight from Oregon to Chicago Midway Airport?

Currently, April is the cheapest month in which you can book a flight from Oregon to Chicago Midway Airport (average of $160). Flying from Oregon to Chicago Midway Airport in November is currently the most expensive (average of $249). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from OR to MDW?

Find hourly flight availability from Oregon to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 15, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Oregon to Chicago Midway Airport as you normally would.

Related info for your journey

Find useful and relevant information for your journey from Oregon to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Oregon to Chicago Midway Airport?

    A quick flight from Oregon to Chicago Midway Airport can take about 6h 26m. Southwest provides one of the quickest options available for as low as $260. The distance from Oregon to Chicago Midway Airport is about 1444 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Oregon to Chicago Midway Airport one-way?

    $87 is the cheapest one-way deal found within the past few days, from Southwest. You may also be able to find cheap deals on Frontier and Delta, with prices starting from $95 and $105, respectively.

  • What are the most popular routes from Oregon to Chicago Midway Airport?

    When deciding which route to take from Oregon to Chicago Midway Airport consider Portland - Chicago Midway, Boise Air Term. Gowen Fld - Chicago Midway or Eugene - Chicago Midway as they are the most popular.

  • What are the cheapest flights from Oregon to Chicago Midway Airport?

    Looking at all options, your cheapest flight can be booked for $98. While the most popular route (Portland - Chicago Midway) can be booked for $212 on average, our data indicates $304 when flying from Oregon to Chicago Midway Airport.

  • Can I find deals for flights from Oregon to Midway that include hotel bookings?

    Yes. In addition to deals on Oregon to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Oregon to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Oregon to Midway.

  • Can I find deals for business class flights from Oregon to Midway?

    Yes. Cheapflights offers flight deals from Oregon to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Oregon to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Oregon to Chicago Midway Airport (average of $160). Flying from Oregon to Chicago Midway Airport in November is currently the most expensive (average of $249). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Oregon to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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Dallas/Fort Worth to Midway flights
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Fort Lauderdale to O'Hare Intl flights
Hobby to Midway flights
Love Field to Midway flights
Denver to Midway flights
Seattle to Midway flights
Providence to O'Hare Intl flights
Reagan-National to Midway flights

Top 3 airlines flying from Oregon to Midway

Discover the top 3 airlines that operate flights from Oregon to Midway. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$108Average$288FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$233Average$443FlexibilityNo cancel feeOn-time63%
DeltaCheapest$256Average$377FlexibilityNo cancel feeOn-timeN/A

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