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Midway

$108+ 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 9/27. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — MDW
Aug 4 — Aug 111
Mon 8/4
Mon 8/11
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 July 30, 2025.

Round-trip from

$205
(Southwest)

One-way from

$108
(Delta)

Popular in

March

Cheapest in

January

Average price

$317

Good round-trip deal

$250 or less

Good one-way deal

$179 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. 10% potential increase in price ($38 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 30, 2025.

This Southwest deal was found by Cheapflights users on 7/28. 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.
Tue 8/261:30 pmPDX - MDW
Nonstop4h 00mSouthwest
Sat 8/302:10 pmMDW - PDX
Nonstop4h 15mSouthwest
Deal found 7/28$205
This Delta deal was found by Cheapflights users on 7/30. 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.
Sat 8/3010:05 pmPDX - MDW
1 stop9h 31mDelta
Tue 9/231:43 pmMDW - PDX
1 stop9h 13mDelta
Deal found 7/30$208
This Delta deal was found by Cheapflights users on 7/28. 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.
Sat 9/205:25 amBOI - MDW
1 stop6h 38mDelta
Wed 10/19:20 amMDW - BOI
1 stop5h 55mDelta
Deal found 7/28$215
This Southwest deal was found by Cheapflights users on 7/28. 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.
Tue 9/2312:45 pmBOI - MDW
1 stop8h 15mSouthwest
Tue 10/77:10 amMDW - BOI
1 stop7h 35mSouthwest
Deal found 7/28$235
This Frontier deal was found by Cheapflights users on 7/29. 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.
Sat 8/166:35 amPDX - MDW
1 stop12h 19mFrontier
Fri 8/226:31 pmMDW - PDX
1 stop7h 44mFrontier
Deal found 7/29$248
This Southwest deal was found by Cheapflights users on 7/29. 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.
Tue 8/196:50 amEUG - MDW
1 stop7h 15mSouthwest
Thu 8/218:00 amMDW - EUG
1 stop10h 35mSouthwest
Deal found 7/29$292
This Delta deal was found by Cheapflights users on 7/30. 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.
Sat 10/116:00 amMFR - MDW
2 stops9h 43mDelta
Sat 10/1811:10 amMDW - MFR
2 stops13h 56mDelta
Deal found 7/30$319
This Delta deal was found by Cheapflights users on 7/29. 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.
Wed 9/35:45 amEUG - MDW
2 stops9h 52mDelta
Sat 9/61:43 pmMDW - EUG
2 stops11h 11mDelta
Deal found 7/29$320
This Delta deal was found by Cheapflights users on 7/30. 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.
Sat 9/137:30 pmRDM - MDW
2 stops11h 23mDelta
Sat 9/209:20 amMDW - RDM
2 stops11h 30mDelta
Deal found 7/30$329

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 July 30, 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

PortlandChicago

PDX - MDW

PDXMDW

Portland

Tue 8/26

1:30 pm-7:30 pm

Nonstop4h 00m

Chicago Midway

Sat 8/30

2:10 pm-4:25 pm

Nonstop4h 15m

$205

PortlandChicago

PDX - MDW

PDXMDW

Portland

Sat 8/30

10:05 pm-9:36 am

1 stop9h 31m

Chicago Midway

Tue 9/23

1:43 pm-8:56 pm

1 stop9h 13m

$208

BoiseChicago

BOI - MDW

BOIMDW

Boise Air Term. Gowen Fld

Sat 9/20

5:25 am-1:03 pm

1 stop6h 38m

Chicago Midway

Sat 10/4

7:15 pm-11:59 pm

1 stop5h 44m

$215

BoiseChicago

BOI - MDW

BOIMDW

Boise Air Term. Gowen Fld

Tue 9/23

12:45 pm-10:00 pm

1 stop8h 15m

Chicago Midway

Tue 10/7

7:10 am-1:45 pm

1 stop7h 35m

$235

PortlandChicago

PDX - MDW

PDXMDW

Portland

Sat 8/16

6:35 am-8:54 pm

1 stop12h 19m

Chicago Midway

Fri 8/22

6:31 pm-12:15 am

1 stop7h 44m

$248

EugeneChicago

EUG - MDW

EUGMDW

Eugene

Tue 8/19

6:50 am-4:05 pm

1 stop7h 15m

Chicago Midway

Thu 8/21

8:00 am-4:35 pm

1 stop10h 35m

$292

MedfordChicago

MFR - MDW

MFRMDW

Medford

Sat 10/11

6:00 am-5:43 pm

2 stops9h 43m

Chicago Midway

Sat 10/18

11:10 am-11:06 pm

2 stops13h 56m

$319

EugeneChicago

EUG - MDW

EUGMDW

Eugene

Wed 9/3

5:45 am-5:37 pm

2 stops9h 52m

Chicago Midway

Sat 9/6

1:43 pm-10:54 pm

2 stops11h 11m

$320

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Sat 9/13

7:30 pm-8:53 am

2 stops11h 23m

Chicago Midway

Sat 9/20

9:20 am-6:50 pm

2 stops11h 30m

$329

BoiseChicago

BOI - MDW

BOIMDW

Boise Air Term. Gowen Fld

Sat 9/27

5:25 am-1:03 pm

1 stop6h 38m

$108

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/28

Showing 1-10 of 21 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 July 30, 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.

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated July 30, 2025.
Read through reviews of airlines operating flights from Oregon to Chicago Midway Airport, such as Southwest, Delta, and Frontier. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,241 reviews

Entertainment

7.5

Food

7.0

Overall

8.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Entertainment

7.5

Food

7.0

Overall

8.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,980 reviews
Southwest
8.0
Very good
4,241 reviews

Entertainment

7.5

Food

7.0

Overall

8.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Frontier
5.9
Fair
3,237 reviews
Southwest
8.0
Very good
4,241 reviews

Entertainment

7.5

Food

7.0

Overall

8.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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.

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

    $108 is the cheapest one-way deal found within the past few days, from Delta. You may also be able to find cheap deals on Southwest and Frontier, with prices starting from $114 and $119, 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, Bend/Redmond - Chicago Midway or Boise Air Term. Gowen Fld - 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 $108. While the most popular route (Portland - Chicago Midway) can be booked for $197 on average our data indicates $288 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
Valparaiso
Chesterton

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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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Top 2 airlines flying from Oregon to Midway

Discover the top 2 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 July 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$108Average$261FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$249Average$443FlexibilityNo cancel feeOn-time63%

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