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$99+ 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 8/31. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PDX
ago. 3 — ago. 101
dom. 8/3
dom. 8/10
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 julio 29, 2025.

Round-trip from

$203
(Southwest)

One-way from

$99
(Southwest)

Popular in

December

Cheapest in

September

Average price

$317

Good round-trip deal

$166 or less

Good one-way deal

$144 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. 4% potential increase in price ($14 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in July 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 julio 29, 2025.

This Southwest deal was found by Cheapflights users on 7/28. 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.
sáb. 8/302:10 pmMDW - PDX
Nonstop4h 15mSouthwest
sáb. 9/66:00 amPDX - MDW
Nonstop4h 00mSouthwest
Deal found 7/28$203
This Delta deal was found by Cheapflights users on 7/28. 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 - PDX
1 stop8h 36mDelta
vie. 9/1212:45 amPDX - MDW
1 stop6h 08mDelta
Deal found 7/28$223
This Delta deal was found by Cheapflights users on 7/28. 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. 9/179:20 amMDW - BOI
1 stop5h 55mDelta
dom. 9/215:25 amBOI - MDW
1 stop6h 38mDelta
Deal found 7/28$225
This Southwest deal was found by Cheapflights users on 7/27. 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.
mié. 9/32:15 pmMDW - BOI
1 stop8h 55mSouthwest
vie. 9/51:10 pmBOI - MDW
Nonstop3h 25mSouthwest
Deal found 7/27$245
This Frontier deal was found by Cheapflights users on 7/26. 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.
sáb. 8/162:44 pmMDW - PDX
1 stop10h 40mFrontier
dom. 8/176:35 amPDX - MDW
1 stop12h 19mFrontier
Deal found 7/26$248
This Delta deal was found by Cheapflights users on 7/28. 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. 10/712:48 pmMDW - RDM
2 stops12h 58mDelta
sáb. 10/117:00 amRDM - MDW
2 stops8h 43mDelta
Deal found 7/28$289
This Southwest deal was found by Cheapflights users on 7/28. 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.
mié. 8/278:20 amMDW - EUG
1 stop6h 05mSouthwest
mié. 9/36:50 amEUG - MDW
1 stop10h 45mSouthwest
Deal found 7/28$311
This Delta deal was found by Cheapflights users on 7/28. 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. 10/211:48 pmMDW - MFR
2 stops11h 18mDelta
mié. 10/296:00 amMFR - MDW
2 stops9h 43mDelta
Deal found 7/28$319
This Delta deal was found by Cheapflights users on 7/28. 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. 8/271:08 pmMDW - EUG
2 stops11h 46mDelta
mié. 9/35:45 amEUG - MDW
2 stops9h 52mDelta
Deal found 7/28$359

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 julio 29, 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

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

sáb. 8/30

2:10 pm-4:25 pm

Nonstop4h 15m

Portland

sáb. 9/6

6:00 am-12:00 pm

Nonstop4h 00m

$203

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

sáb. 8/30

1:08 pm-7:44 pm

1 stop8h 36m

Portland

vie. 9/12

12:45 am-8:53 am

1 stop6h 08m

$223

ChicagoBoise

MDW - BOI

MDWBOI

Chicago Midway

mié. 9/17

9:20 am-2:15 pm

1 stop5h 55m

Boise Air Term. Gowen Fld

dom. 9/21

5:25 am-1:03 pm

1 stop6h 38m

$225

ChicagoBoise

MDW - BOI

MDWBOI

Chicago Midway

mié. 9/3

2:15 pm-10:10 pm

1 stop8h 55m

Boise Air Term. Gowen Fld

vie. 9/5

1:10 pm-5:35 pm

Nonstop3h 25m

$245

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

sáb. 8/16

2:44 pm-11:24 pm

1 stop10h 40m

Portland

dom. 8/17

6:35 am-8:54 pm

1 stop12h 19m

$248

ChicagoRedmond

MDW - RDM

MDWRDM

Chicago Midway

mar. 10/7

12:48 pm-11:46 pm

2 stops12h 58m

Bend/Redmond

sáb. 10/11

7:00 am-5:43 pm

2 stops8h 43m

$289

ChicagoEugene

MDW - EUG

MDWEUG

Chicago Midway

mié. 8/27

8:20 am-12:25 pm

1 stop6h 05m

Eugene

mié. 9/3

6:50 am-7:35 pm

1 stop10h 45m

$311

ChicagoMedford

MDW - MFR

MDWMFR

Chicago Midway

mar. 10/21

1:48 pm-11:06 pm

2 stops11h 18m

Medford

mié. 10/29

6:00 am-5:43 pm

2 stops9h 43m

$319

ChicagoEugene

MDW - EUG

MDWEUG

Chicago Midway

mié. 8/27

1:08 pm-10:54 pm

2 stops11h 46m

Eugene

mié. 9/3

5:45 am-5:37 pm

2 stops9h 52m

$359

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

dom. 8/31

5:55 am-9:55 am

1 stop6h 00m

$99

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/28

Showing 1-10 of 19 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 julio 29, 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 julio 29, 2025.
Read reviews from past customers who have flown Southwest, Delta, 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
4,238 reviews

Crew

8.6

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Food

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,238 reviews
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Food

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,977 reviews
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Food

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Frontier
5.9
Fair
3,238 reviews
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Food

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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 ($99), Delta ($100), and Frontier ($108).

  • 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 $233, our data indicates the cheapest price to be $98. The most popular route (Chicago Midway - Portland), is priced around $203.

  • 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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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 julio 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$108Average$191FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$238Average$475FlexibilityNo cancel feeOn-time63%

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