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$78+ 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 6/14. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PDX
Apr 22 — Apr 291
Tue 4/22
Tue 4/29
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 April 17, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$217
(Delta)

One-way from

$78
(Southwest)

Popular in

December

Cheapest in

September

Average price

$307

Good round-trip deal

$293 or less

Good one-way deal

$144 or less
Provider with most accurate pricing for Chicago (CHI)-Portland flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Portland flights.
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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. 5% potential increase in price ($20 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 April 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 April 17, 2025.

This Delta deal was found by Cheapflights users on 4/16. 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.
Sat 5/311:55 pmMDW - BOI
1 stop7h 39mDelta
Sat 6/75:35 amBOI - MDW
1 stop6h 40mDelta
Deal found 4/16$197
This Frontier deal was found by Cheapflights users on 4/15. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/158:03 pmMDW - PDX
1 stop6h 35mFrontier
Sat 5/2412:48 pmPDX - MDW
1 stop6h 05mFrontier
Deal found 4/15$228
This Southwest deal was found by Cheapflights users on 4/16. 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 5/284:30 pmMDW - PDX
Nonstop4h 20mSouthwest
Sat 5/316:45 amPDX - MDW
Nonstop4h 00mSouthwest
Deal found 4/16$244
This Southwest deal was found by Cheapflights users on 4/16. 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 5/78:35 amMDW - BOI
1 stop9h 10mSouthwest
Thu 5/81:50 pmBOI - MDW
1 stop9h 05mSouthwest
Deal found 4/16$244
This Delta deal was found by Cheapflights users on 4/15. 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 5/175:25 pmMDW - PDX
1 stop6h 50mDelta
Sat 5/2411:15 pmPDX - MDW
1 stop7h 25mDelta
Deal found 4/15$249
This Delta deal was found by Cheapflights users on 4/16. 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.
Sat 5/311:55 pmMDW - RDM
2 stops10h 17mDelta
Sat 6/77:29 pmRDM - MDW
2 stops11h 15mDelta
Deal found 4/16$269
This Southwest deal was found by Cheapflights users on 4/16. 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 9/176:10 amMDW - EUG
1 stop6h 50mSouthwest
Mon 9/226:50 amEUG - MDW
1 stop6h 25mSouthwest
Deal found 4/16$351
This eDestinos deal was found by Cheapflights users on 4/17. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/16:25 amMDW - EUG
1 stop10h 24mMultiple Airlines
Sun 6/89:41 pmEUG - MDW
1 stop15h 15mMultiple Airlines
Deal found 4/17$374
This eDestinos deal was found by Cheapflights users on 4/17. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/16:25 amMDW - MFR
2 stops16h 42mMultiple Airlines
Sun 6/89:51 pmMFR - MDW
1 stop15h 05mMultiple Airlines
Deal found 4/17$383
This Delta deal was found by Cheapflights users on 4/16. 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.
Sat 5/311:08 pmMDW - EUG
2 stops12h 07mDelta
Sat 6/75:45 amEUG - MDW
2 stops10h 02mDelta
Deal found 4/16$423
This Delta deal was found by Cheapflights users on 4/17. 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 5/241:08 pmMDW - MFR
2 stops11h 39mDelta
Sun 5/255:45 amMFR - MDW
2 stops10h 00mDelta
Deal found 4/17$423

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 April 17, 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 5/31

1:55 pm-8:34 pm

1 stop7h 39m

Boise Air Term. Gowen Fld

Sat 6/7

5:35 am-1:15 pm

1 stop6h 40m

$197

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Thu 5/15

8:03 pm-12:38 am

1 stop6h 35m

Portland

Sat 5/24

12:48 pm-8:53 pm

1 stop6h 05m

$228

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Wed 5/28

4:30 pm-6:50 pm

Nonstop4h 20m

Portland

Sat 5/31

6:45 am-12:45 pm

Nonstop4h 00m

$244

ChicagoBoise

MDW - BOI

MDWBOI

Chicago Midway

Wed 5/7

8:35 am-4:45 pm

1 stop9h 10m

Boise Air Term. Gowen Fld

Thu 5/8

1:50 pm-11:55 pm

1 stop9h 05m

$244

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Sat 5/17

5:25 pm-10:15 pm

1 stop6h 50m

Portland

Sat 5/24

11:15 pm-8:40 am

1 stop7h 25m

$249

ChicagoRedmond

MDW - RDM

MDWRDM

Chicago Midway

Sat 5/31

1:55 pm-10:12 pm

2 stops10h 17m

Bend/Redmond

Sat 6/7

7:29 pm-8:44 am

2 stops11h 15m

$269

ChicagoEugene

MDW - EUG

MDWEUG

Chicago Midway

Wed 6/18

5:25 pm-11:30 pm

1 stop8h 05m

Eugene

Tue 6/24

12:20 pm-12:55 am

2 stops10h 35m

$356

ChicagoEugene

MDW - EUG

MDWEUG

Chicago Midway

Sun 6/1

6:25 am-2:49 pm

1 stop10h 24m

Eugene

Sun 6/8

9:41 pm-2:56 pm

1 stop15h 15m

$374

ChicagoMedford

MDW - MFR

MDWMFR

Chicago Midway

Sun 6/1

6:25 am-9:07 pm

2 stops16h 42m

Medford

Sun 6/8

9:51 pm-2:56 pm

1 stop15h 05m

$383

ChicagoEugene

MDW - EUG

MDWEUG

Chicago Midway

Sat 5/31

1:08 pm-11:15 pm

2 stops12h 07m

Eugene

Sat 6/7

5:45 am-5:47 pm

2 stops10h 02m

$423

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/16

Showing 1-10 of 25 results
1
2
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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 $369). 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 April 17, 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.

Rainfall in Oregon by month

Plan your trip to Oregon by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Oregon ranges from 0.7 - 5.6 inches per month. November is typically the wettest month, when rainfall can reach 5.6 in. July is typically the driest time to visit Oregon when rainfall is around 0.7 in.

Temperature in Oregon by month

Plan your trip to Oregon by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Oregon, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 69.8 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 41.0 F).

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 April 17, 2025.
Read through reviews of airlines operating flights from Chicago to Oregon, such as Southwest, Delta and Allegiant Air. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,280 reviews

Overall

8.0

Comfort

8.0

Entertainment

7.6

Crew

8.6

Food

7.1

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.0
Very good
4,280 reviews
Southwest
8.0
Very good
4,280 reviews

Overall

8.0

Comfort

8.0

Entertainment

7.6

Crew

8.6

Food

7.1

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,917 reviews
Southwest
8.0
Very good
4,280 reviews

Overall

8.0

Comfort

8.0

Entertainment

7.6

Crew

8.6

Food

7.1

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Allegiant Air
7.3
Good
734 reviews
Southwest
8.0
Very good
4,280 reviews

Overall

8.0

Comfort

8.0

Entertainment

7.6

Crew

8.6

Food

7.1

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Frontier
6.0
Okay
3,281 reviews
Southwest
8.0
Very good
4,280 reviews

Overall

8.0

Comfort

8.0

Entertainment

7.6

Crew

8.6

Food

7.1

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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.

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

    The cheapest airlines for a one-way flight from Chicago Midway Airport to Oregon are Southwest ($78), Delta ($88), and Frontier ($96).

  • 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 $275, our data indicates the cheapest price to be $89. The most popular route (Chicago Midway - Portland), is priced around $201.

  • 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 $369). 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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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 April 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$108Average$179FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$238Average$433FlexibilityNo cancel feeOn-time63%

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