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Midway

$89+ 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 1/15. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — MDW
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap 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 December 18, 2025.

This Delta deal was found by Cheapflights users on 12/16. 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.
Sun 12/211:55 pmBOI - MDW
1 stop7h 27mDelta
Wed 12/315:59 pmMDW - BOI
1 stop6h 54mDelta
Deal found 12/16$378
This Southwest deal was found by Cheapflights users on 12/16. 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 12/312:15 pmPDX - MDW
1 stop6h 40mSouthwest
Sun 1/47:30 pmMDW - PDX
Nonstop4h 30mSouthwest
Deal found 12/16$379
This Delta deal was found by Cheapflights users on 12/16. 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 12/225:30 amBOI - MDW
2 stops9h 50mDelta
Wed 12/315:59 pmMDW - BOI
1 stop6h 54mDelta
Deal found 12/16$383
This Delta deal was found by Cheapflights users on 12/16. 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 12/175:35 amBOI - MDW
1 stop6h 35mDelta
Wed 12/245:59 pmMDW - BOI
1 stop6h 54mDelta
Deal found 12/16$391
This Southwest deal was found by Cheapflights users on 12/15. 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.
Sat 12/275:00 amPDX - MDW
1 stop9h 45mSouthwest
Sat 1/248:35 amMDW - PDX
Nonstop4h 40mSouthwest
Deal found 12/15$422
This Southwest deal was found by Cheapflights users on 12/16. 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.
Sat 12/277:25 pmBOI - MDW
2 stops8h 50mSouthwest
Sat 1/38:00 pmMDW - BOI
1 stop6h 40mSouthwest
Deal found 12/16$434
This Delta deal was found by Cheapflights users on 12/15. 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 12/2710:05 pmPDX - MDW
1 stop9h 00mDelta
Fri 1/231:49 pmMDW - PDX
1 stop8h 43mDelta
Deal found 12/15$442
This Southwest deal was found by Cheapflights users on 12/16. 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 12/175:15 amBOI - MDW
2 stops6h 20mSouthwest
Wed 12/241:15 pmMDW - BOI
2 stops10h 10mSouthwest
Deal found 12/16$456
This Southwest deal was found by Cheapflights users on 12/16. 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 12/305:10 amPDX - MDW
1 stop8h 25mSouthwest
Thu 1/15:15 pmMDW - PDX
1 stop7h 15mSouthwest
Deal found 12/16$468
This Southwest deal was found by Cheapflights users on 12/16. 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 12/303:00 pmPDX - MDW
1 stop8h 10mSouthwest
Fri 1/28:00 amMDW - PDX
1 stop10h 35mSouthwest
Deal found 12/16$478
This Southwest deal was found by Cheapflights users on 12/16. 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 12/284:25 pmBOI - MDW
1 stop6h 45mSouthwest
Sun 1/47:20 pmMDW - BOI
1 stop6h 20mSouthwest
Deal found 12/16$479
This Southwest deal was found by Cheapflights users on 12/16. 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.
Mon 12/225:00 amBOI - MDW
2 stops8h 50mSouthwest
Wed 12/311:15 pmMDW - BOI
2 stops10h 10mSouthwest
Deal found 12/16$481

Find flight deals from Oregon to Midway

Keep the following information in mind while searching for Oregon to Midway flight deals. Data was last updated December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$236
(Southwest)

One-way from

$89
(Kiwi.com)

Popular in

March

Cheapest in

August

Average price

$415

Good round-trip deal

$316 or less

Good one-way deal

$166 or less
Provider with most accurate pricing for Portland-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Portland-Chicago (CHI) flights.
Search Deals
From Oregon to Chicago Midway
Search Deals
One-way flight from Oregon to Chicago Midway
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($25 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Oregon to Chicago Midway.
Search Deals
Price to beat on a one-way flight from Oregon to Chicago Midway.
Search Deals

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 December 18, 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

Sat 1/10

9:55 am-7:45 pm

1 stop7h 50m

Chicago Midway

Sat 1/17

4:05 pm-8:30 pm

1 stop6h 25m

$236

PortlandChicago

PDX - MDW

PDXMDW

Portland

Fri 2/13

12:40 am-11:03 am

1 stop8h 23m

Chicago Midway

Tue 2/17

1:49 pm-8:30 pm

1 stop8h 41m

$237

PortlandChicago

PDX - MDW

PDXMDW

Portland

Tue 1/13

11:25 am-10:40 pm

1 stop9h 15m

Chicago Midway

Thu 1/15

8:10 am-10:45 am

Nonstop4h 35m

$237

PortlandChicago

PDX - MDW

PDXMDW

Portland

Tue 1/13

11:44 am-10:07 pm

1 stop8h 23m

Chicago Midway

Tue 1/20

1:49 pm-8:32 pm

1 stop8h 43m

$237

PortlandChicago

PDX - MDW

PDXMDW

Portland

Thu 1/15

2:25 pm-10:25 pm

1 stop6h 00m

Chicago Midway

Tue 1/20

3:35 pm-6:00 pm

Nonstop4h 25m

$237

PortlandChicago

PDX - MDW

PDXMDW

Portland

Fri 1/23

12:40 am-11:05 am

1 stop8h 25m

Chicago Midway

Tue 1/27

1:49 pm-8:32 pm

1 stop8h 43m

$237

PortlandChicago

PDX - MDW

PDXMDW

Portland

Fri 1/30

6:30 am-12:25 pm

Nonstop3h 55m

Chicago Midway

Mon 2/2

3:35 pm-6:00 pm

Nonstop4h 25m

$237

PortlandChicago

PDX - MDW

PDXMDW

Portland

Thu 3/5

5:20 am-11:15 am

Nonstop3h 55m

Chicago Midway

Mon 3/9

10:20 pm-12:45 am

Nonstop4h 25m

$237

PortlandChicago

PDX - MDW

PDXMDW

Portland

Thu 1/8

6:30 am-12:25 pm

Nonstop3h 55m

Chicago Midway

Tue 1/13

3:35 pm-6:00 pm

Nonstop4h 25m

$237

BoiseChicago

BOI - MDW

BOIMDW

Boise Air Term. Gowen Fld

Wed 1/14

1:41 pm-10:07 pm

1 stop7h 26m

Chicago Midway

Wed 1/21

1:49 pm-8:55 pm

1 stop8h 06m

$269

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/15

Showing 1-10 of 59 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 $292). 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 December 18, 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 $118. While the most popular route (Portland - Chicago Midway) can be booked for $217 on average, our data indicates $341 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 $292). 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
Lansing
Merrillville
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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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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$238Average$415FlexibilityNo cancel feeOn-time63%
DeltaCheapest$268Average$377FlexibilityNo cancel feeOn-timeN/A

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