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$84+ Cheap flights from Midway (MDW) to Oregon

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 10/18. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PDX
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheap flight deals from Midway to Oregon

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

Round-trip from

$215
(Delta)

One-way from

$84
(Delta)

Popular in

December

Cheapest in

January

Average price

$278

Good round-trip deal

$249 or less

Good one-way deal

$89 or less
From Chicago Midway to Oregon
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One-way flight from Chicago Midway to Oregon
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Highest demand for flights based on searches. 2% potential increase in price ($8 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($11 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 Chicago Midway to Oregon.
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Price to beat on a one-way flight from Chicago Midway to Oregon.
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Find flight deals from Midway to Oregon

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

This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/187:10 pmMDW - BOI
1 stop5h 44mDelta
Sat 10/251:39 pmBOI - MDW
1 stop7h 35mDelta
Deal found 9/13$215
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.
Sat 10/253:45 pmMDW - PDX
Nonstop4h 20mSouthwest
Fri 10/3110:15 amPDX - MDW
1 stop7h 45mSouthwest
Deal found 9/13$219
This Southwest deal was found by Cheapflights users on 9/15. 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.
Tue 10/218:25 pmMDW - PDX
Nonstop4h 25mSouthwest
Wed 10/291:25 pmPDX - MDW
Nonstop3h 55mSouthwest
Deal found 9/15$231
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 10/179:30 pmMDW - PDX
Nonstop4h 25mSouthwest
Tue 10/211:25 pmPDX - MDW
Nonstop3h 55mSouthwest
Deal found 9/14$244
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.
Mon 10/69:47 pmMDW - PDX
2 stops16h 01mFrontier
Sat 10/1112:43 pmPDX - MDW
2 stops21h 01mFrontier
Deal found 9/13$249
This Delta deal was found by Cheapflights users on 9/15. 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.
Tue 10/211:48 pmMDW - PDX
1 stop8h 38mDelta
Tue 10/2812:40 amPDX - MDW
1 stop6h 15mDelta
Deal found 9/15$251
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 11/149:50 pmMDW - PDX
Nonstop4h 30mSouthwest
Tue 11/188:00 amPDX - MDW
1 stop7h 10mSouthwest
Deal found 9/14$254
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 10/224:35 pmMDW - PDX
1 stop6h 40mSouthwest
Sat 10/255:05 amPDX - MDW
2 stops9h 20mSouthwest
Deal found 9/14$256
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.
Tue 10/146:05 amMDW - BOI
1 stop6h 45mSouthwest
Tue 10/214:15 pmBOI - MDW
1 stop5h 25mSouthwest
Deal found 9/14$265
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 11/59:40 amMDW - EUG
1 stop6h 10mSouthwest
Mon 11/104:45 pmEUG - MDW
2 stops10h 20mSouthwest
Deal found 9/14$293
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/301:43 pmMDW - EUG
2 stops10h 59mDelta
Tue 10/287:00 amEUG - MDW
2 stops8h 43mDelta
Deal found 9/12$294
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 11/129:40 amMDW - EUG
1 stop6h 10mSouthwest
Sat 11/156:40 amEUG - MDW
2 stops11h 45mSouthwest
Deal found 9/13$299

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Oregon 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 Chicago Midway Airport to Oregon that are best for you.

Fly from

Midway

Fly to

Oregon

Route

Depart

Return

Price

ChicagoBoise

MDW - BOI

MDWBOI

Chicago Midway

Sat 10/18

7:10 pm-11:54 pm

1 stop5h 44m

Boise Air Term. Gowen Fld

Sat 10/25

1:39 pm-10:14 pm

1 stop7h 35m

$215

ChicagoBoise

MDW - BOI

MDWBOI

Chicago Midway

Wed 11/12

9:41 am-2:04 pm

1 stop5h 23m

Boise Air Term. Gowen Fld

Sat 11/15

5:35 am-1:07 pm

1 stop6h 32m

$215

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Sat 10/25

3:45 pm-6:05 pm

Nonstop4h 20m

Portland

Fri 10/31

6:00 am-6:05 pm

1 stop10h 05m

$224

ChicagoBoise

MDW - BOI

MDWBOI

Chicago Midway

Tue 3/3

9:20 am-2:09 pm

1 stop5h 49m

Boise Air Term. Gowen Fld

Wed 3/4

5:40 am-6:34 pm

2 stops11h 54m

$236

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Tue 10/21

8:25 pm-10:50 pm

Nonstop4h 25m

Portland

Wed 10/29

5:10 am-2:05 pm

1 stop6h 55m

$241

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Thu 12/25

8:45 am-3:20 pm

1 stop8h 35m

Portland

Mon 1/5

7:00 pm-5:05 am

1 stop8h 05m

$241

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Sat 1/17

9:45 am-4:40 pm

2 stops8h 55m

Portland

Fri 1/23

11:30 am-9:15 pm

1 stop7h 45m

$247

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Sat 10/25

3:00 pm-8:26 pm

1 stop7h 26m

Portland

Thu 10/30

12:40 am-8:55 am

1 stop6h 15m

$257

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Fri 10/10

9:30 pm-11:55 pm

Nonstop4h 25m

Portland

Tue 10/14

6:15 am-7:20 pm

1 stop11h 05m

$259

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Fri 10/17

9:30 pm-11:55 pm

Nonstop4h 25m

Portland

Sat 10/25

2:00 pm-5:15 am

1 stop13h 15m

$259

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 Midway to Oregon

Have a flexible travel schedule? Discover the best time to fly to Oregon from Midway 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 Chicago Midway Airport to Oregon

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

Currently, November is the cheapest month in which you can book a flight from Chicago Midway Airport to Oregon (average of $277). Flying from Chicago Midway Airport to Oregon in March is currently the most expensive (average of $368). 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 MDW to OR?

Find hourly flight availability from Midway to Oregon. 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 Chicago Midway Airport to Oregon as you normally would.

Reviews of airlines servicing Oregon

Get insights into the airlines that provide service to Oregon. 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 Oregon. Reviews last updated September 15, 2025.
Read reviews from past customers who have flown Southwest and Frontier from Chicago Midway Airport to Oregon. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,245 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,245 reviews
Southwest
8.0
Very good
4,245 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Frontier
5.8
Fair
3,173 reviews
Southwest
8.0
Very good
4,245 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

Find useful and relevant information for your journey from Midway to Oregon. 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 Chicago Midway Airport to Oregon?

    There are many flights that can get you from Chicago Midway Airport to Oregon in 4h 20m. Fly via Delta or Southwest to get the fastest option. Chicago Midway Airport and Oregon are separated by a distance of 1746 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    Most travelers choose Chicago Midway - Portland, Chicago Midway - Boise Air Term. Gowen Fld or Chicago Midway - Eugene when deciding on the best route from Chicago Midway Airport to Oregon.

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

    Looking for the cheapest flight from Chicago Midway Airport to Oregon? While on average our users pay $198, our data indicates the cheapest price to be $65. The most popular route (Chicago Midway - Portland), is priced around $156.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Midway to Oregon 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 Chicago Midway Airport to Oregon?

    Currently, November is the cheapest month in which you can book a flight from Chicago Midway Airport to Oregon (average of $277). Flying from Chicago Midway Airport to Oregon in March is currently the most expensive (average of $368). 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.

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Alternative routes for Midway to Oregon

See prices for flight routes from nearby airports that may be better suited for you.
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Midway to Seattle flights

Top 2 airlines flying from Midway to Oregon

Discover the top 2 airlines that operate flights from Midway to Oregon. 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$191FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$238Average$451FlexibilityNo cancel feeOn-time63%

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