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$91+ 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 8/12. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PDX
jun. 17 — jun. 241
mar. 6/17
mar. 6/24
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 junio 12, 2025.

Round-trip from

$195
(Delta)

One-way from

$91
(Delta)

Popular in

December

Cheapest in

September

Average price

$313

Good round-trip deal

$303 or less

Good one-way deal

$135 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. 5% potential increase in price ($16 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 June 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 junio 12, 2025.

This Delta deal was found by Cheapflights users on 6/10. 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.
mié. 8/209:15 amMDW - BOI
1 stop5h 46mDelta
mié. 10/221:43 pmBOI - MDW
1 stop7h 01mDelta
Deal found 6/10$195
This Southwest deal was found by Cheapflights users on 6/11. 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.
lun. 9/18:50 pmMDW - PDX
Nonstop4h 15mSouthwest
vie. 9/512:35 pmPDX - MDW
1 stop9h 15mSouthwest
Deal found 6/11$217
This Delta deal was found by Cheapflights users on 6/11. 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.
mar. 7/291:46 pmMDW - PDX
1 stop8h 37mDelta
vie. 8/812:40 amPDX - MDW
1 stop6h 05mDelta
Deal found 6/11$247
This Southwest deal was found by Cheapflights users on 6/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 8/281:05 pmMDW - BOI
Nonstop3h 45mSouthwest
dom. 8/313:00 pmBOI - MDW
Nonstop3h 20mSouthwest
Deal found 6/12$274
This Frontier deal was found by Cheapflights users on 6/12. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 9/254:29 pmMDW - PDX
1 stop9h 47mFrontier
dom. 9/286:05 amPDX - MDW
1 stop10h 56mFrontier
Deal found 6/12$288
This Delta deal was found by Cheapflights users on 6/11. 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.
mar. 10/72:00 pmMDW - RDM
2 stops10h 44mDelta
sáb. 10/117:25 pmRDM - MDW
2 stops11h 21mDelta
Deal found 6/11$289
This Southwest deal was found by Cheapflights users on 6/10. 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.
jue. 10/237:55 amMDW - EUG
1 stop8h 30mSouthwest
lun. 10/276:05 amEUG - MDW
1 stop12h 30mSouthwest
Deal found 6/10$333
This Delta deal was found by Cheapflights users on 6/11. 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.
sáb. 8/301:08 pmMDW - EUG
2 stops11h 38mDelta
jue. 9/46:30 amEUG - MDW
2 stops10h 07mDelta
Deal found 6/11$362
This Delta deal was found by Cheapflights users on 6/11. 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.
vie. 7/251:09 pmMDW - MFR
2 stops12h 44mDelta
mar. 7/296:15 amMFR - MDW
2 stops9h 24mDelta
Deal found 6/11$718

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 junio 12, 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

mié. 8/20

9:15 am-2:01 pm

1 stop5h 46m

Boise Air Term. Gowen Fld

mié. 10/22

1:43 pm-9:44 pm

1 stop7h 01m

$195

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

lun. 9/1

8:50 pm-11:05 pm

Nonstop4h 15m

Portland

vie. 9/5

12:35 pm-11:50 pm

1 stop9h 15m

$217

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

mar. 7/29

1:46 pm-8:23 pm

1 stop8h 37m

Portland

vie. 8/8

12:40 am-8:45 am

1 stop6h 05m

$247

ChicagoBoise

MDW - BOI

MDWBOI

Chicago Midway

jue. 8/28

1:05 pm-3:50 pm

Nonstop3h 45m

Boise Air Term. Gowen Fld

dom. 8/31

3:00 pm-7:20 pm

Nonstop3h 20m

$274

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

jue. 9/25

4:29 pm-12:16 am

1 stop9h 47m

Portland

dom. 9/28

6:05 am-7:01 pm

1 stop10h 56m

$288

ChicagoRedmond

MDW - RDM

MDWRDM

Chicago Midway

mar. 10/7

2:00 pm-10:44 pm

2 stops10h 44m

Bend/Redmond

sáb. 10/11

7:25 pm-8:46 am

2 stops11h 21m

$289

ChicagoEugene

MDW - EUG

MDWEUG

Chicago Midway

jue. 10/23

7:55 am-2:25 pm

1 stop8h 30m

Eugene

lun. 10/27

6:05 am-8:35 pm

1 stop12h 30m

$333

ChicagoEugene

MDW - EUG

MDWEUG

Chicago Midway

sáb. 8/30

1:08 pm-10:46 pm

2 stops11h 38m

Eugene

jue. 9/4

6:30 am-6:37 pm

2 stops10h 07m

$362

ChicagoMedford

MDW - MFR

MDWMFR

Chicago Midway

vie. 7/25

1:09 pm-11:53 pm

2 stops12h 44m

Medford

mar. 7/29

6:15 am-5:39 pm

2 stops9h 24m

$718

ChicagoBoise

MDW - BOI

MDWBOI

Chicago Midway

mar. 8/12

7:17 pm-11:54 pm

1 stop5h 37m

$91

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

Showing 1-10 of 24 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 junio 12, 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 junio 12, 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
4,287 reviews

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Overall

8.0

Food

7.1

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Overall

8.0

Food

7.1

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,946 reviews
Southwest
8.0
Very good
4,287 reviews

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Overall

8.0

Food

7.1

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Allegiant Air
7.3
Good
725 reviews
Southwest
8.0
Very good
4,287 reviews

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Overall

8.0

Food

7.1

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Frontier
6.0
Okay
3,295 reviews
Southwest
8.0
Very good
4,287 reviews

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Overall

8.0

Food

7.1

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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 Delta ($91), Southwest ($101), and Allegiant Air ($118).

  • 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 - Bend/Redmond 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 $268, our data indicates the cheapest price to be $89. The most popular route (Chicago Midway - Portland), is priced around $181.

  • 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.

See more FAQs

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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 junio 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$108Average$208FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$237Average$444FlexibilityNo cancel feeOn-time63%

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