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$71+ 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 1/11. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — MDW
Dec 3 — Dec 101
Wed 12/3
Wed 12/10
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 November 3, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$227
(Southwest)

One-way from

$71
(Kiwi.com)

Popular in

March

Cheapest in

August

Average price

$365

Good round-trip deal

$287 or less

Good one-way deal

$186 or less
Provider with most accurate pricing for Portland-Chicago (CHI) flight deals.
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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 ($31 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 November 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 November 3, 2025.

This Booking.com deal was found by Cheapflights users on 11/2. 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 11/1312:52 pmPDX - MDW
1 stop20h 38mFrontier
Mon 11/1712:30 pmMDW - PDX
1 stop25h 26mFrontier
Deal found 11/2$228
This Kiwi.com deal was found by Cheapflights users on 11/2. 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.
Sun 11/233:59 pmPDX - MDW
1 stop20h 32mFrontier
Thu 11/274:00 pmMDW - PDX
2 stops18h 04mFrontier
Deal found 11/2$229
This Southwest deal was found by Cheapflights users on 11/2. 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 12/35:30 amPDX - MDW
1 stop7h 30mSouthwest
Wed 12/105:15 amMDW - PDX
1 stop8h 10mSouthwest
Deal found 11/2$236
This Delta deal was found by Cheapflights users on 11/2. 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.
Tue 12/212:32 amPDX - MDW
1 stop6h 47mDelta
Wed 12/101:50 pmMDW - PDX
1 stop9h 02mDelta
Deal found 11/2$237
This Southwest deal was found by Cheapflights users on 11/2. 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 12/37:15 amPDX - MDW
1 stop7h 50mSouthwest
Mon 12/86:00 pmMDW - PDX
1 stop6h 35mSouthwest
Deal found 11/2$246
This Delta deal was found by Cheapflights users on 11/2. 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.
Thu 12/410:10 pmPDX - MDW
1 stop9h 44mDelta
Wed 12/1012:50 pmMDW - PDX
1 stop8h 45mDelta
Deal found 11/2$247
This Southwest deal was found by Cheapflights users on 11/1. 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 12/127:00 pmPDX - MDW
1 stop8h 05mSouthwest
Mon 12/156:00 pmMDW - PDX
1 stop6h 35mSouthwest
Deal found 11/1$256
This Southwest deal was found by Cheapflights users on 11/2. 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.
Sun 11/233:55 pmPDX - MDW
1 stop6h 10mSouthwest
Thu 11/278:35 amMDW - PDX
Nonstop4h 30mSouthwest
Deal found 11/2$257
This Kiwi.com deal was found by Cheapflights users on 11/1. 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.
Sat 11/1512:52 pmPDX - MDW
2 stops21h 45mFrontier
Sat 11/229:58 pmMDW - PDX
1 stop19h 09mFrontier
Deal found 11/1$260
This Southwest deal was found by Cheapflights users on 10/31. 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 12/510:50 amPDX - MDW
1 stop7h 15mSouthwest
Sun 12/79:50 pmMDW - PDX
Nonstop4h 30mSouthwest
Deal found 10/31$267
This Delta deal was found by Cheapflights users on 11/2. 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.
Mon 12/112:32 amPDX - MDW
1 stop6h 47mDelta
Fri 12/51:50 pmMDW - PDX
1 stop9h 02mDelta
Deal found 11/2$273
This Delta deal was found by Cheapflights users on 11/1. 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.
Thu 12/411:10 amBOI - MDW
2 stops11h 37mDelta
Mon 12/81:50 pmMDW - BOI
2 stops11h 14mDelta
Deal found 11/1$302

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 November 3, 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 1/6

7:25 am-5:15 pm

1 stop7h 50m

Chicago Midway

Wed 1/7

6:10 am-11:45 am

1 stop7h 35m

$236

PortlandChicago

PDX - MDW

PDXMDW

Portland

Sat 1/17

6:00 am-4:16 pm

1 stop8h 16m

Chicago Midway

Tue 1/27

10:53 am-7:13 pm

1 stop10h 20m

$237

PortlandChicago

PDX - MDW

PDXMDW

Portland

Fri 12/5

6:15 am-12:10 pm

Nonstop3h 55m

Chicago Midway

Wed 12/10

2:35 pm-6:50 pm

1 stop6h 15m

$237

PortlandChicago

PDX - MDW

PDXMDW

Portland

Mon 12/8

6:15 am-12:10 pm

Nonstop3h 55m

Chicago Midway

Fri 12/12

9:50 pm-12:20 am

Nonstop4h 30m

$237

PortlandChicago

PDX - MDW

PDXMDW

Portland

Fri 12/5

10:10 pm-9:54 am

1 stop9h 44m

Chicago Midway

Wed 12/10

1:50 pm-8:52 pm

1 stop9h 02m

$247

PortlandChicago

PDX - MDW

PDXMDW

Portland

Mon 12/8

10:10 pm-9:54 am

1 stop9h 44m

Chicago Midway

Fri 12/12

1:50 pm-8:52 pm

1 stop9h 02m

$257

PortlandChicago

PDX - MDW

PDXMDW

Portland

Sun 2/1

12:40 am-9:08 am

1 stop6h 28m

Chicago Midway

Wed 2/11

1:49 pm-8:32 pm

1 stop8h 43m

$263

PortlandChicago

PDX - MDW

PDXMDW

Portland

Wed 12/10

7:15 am-5:05 pm

1 stop7h 50m

Chicago Midway

Thu 12/11

5:15 am-11:25 am

1 stop8h 10m

$266

PortlandChicago

PDX - MDW

PDXMDW

Portland

Fri 12/5

11:20 pm-8:49 am

1 stop7h 29m

Chicago Midway

Sun 12/7

12:50 pm-7:35 pm

1 stop8h 45m

$273

BoiseChicago

BOI - MDW

BOIMDW

Boise Air Term. Gowen Fld

Mon 3/2

7:05 pm-5:05 am

1 stop9h 00m

Chicago Midway

Wed 3/4

6:00 am-10:40 am

1 stop5h 40m

$292

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/2

Showing 1-10 of 58 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 $137). Flying from Oregon to Chicago Midway Airport in March is currently the most expensive (average of $316). 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 November 3, 2025.

When flying from Oregon to Chicago Midway Airport, the time of day you fly usually plays a role in the price. Save by searching for a flight at noon, which can drop the price by up to 38% versus a flight in the morning.

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 7h 50m. Southwest provides one of the quickest options available for as low as $236. The distance from Oregon to Chicago Midway Airport is about 1746 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 $94. While the most popular route (Portland - Chicago Midway) can be booked for $217 on average, our data indicates $326 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 $137). Flying from Oregon to Chicago Midway Airport in March is currently the most expensive (average of $316). 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
Porter
Benton Harbor

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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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Reagan-National to Midway flights
Cleveland to O'Hare Intl flights
Denver to Midway flights
Minneapolis to Midway flights
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Portland to O'Hare Intl flights
LaGuardia to Midway flights
Fort Lauderdale to O'Hare Intl flights
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Los Angeles to Midway flights
Orlando to Midway flights
Boston to Midway flights
San Jose to O'Hare Intl flights
Hobby to O'Hare Intl flights
Salt Lake City to O'Hare Intl flights
Sacramento to O'Hare Intl flights

Top 4 airlines flying from Oregon to Midway

Discover the top 4 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 November 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$128Average$324FlexibilityNo cancel feeOn-time62%
Alaska AirlinesCheapest$197Average$281FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$246Average$427FlexibilityNo cancel feeOn-time63%
DeltaCheapest$268Average$418FlexibilityNo cancel feeOn-timeN/A

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