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$92+ 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 2/28. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PDX
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheap 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 January 29, 2026.

This Southwest deal was found by Cheapflights users on 1/27. 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.
Tue 2/248:25 am
MDW
-
PDX
1 stop7h 10m
Southwest
Tue 3/36:30 am
PDX
-
MDW
Nonstop3h 55m
Southwest
Deal found 1/27$207
This Delta deal was found by Cheapflights users on 1/28. 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.
Tue 2/241:49 pm
MDW
-
PDX
1 stop8h 41m
Delta
Tue 3/312:09 pm
PDX
-
MDW
1 stop8h 24m
Delta
Deal found 1/28$217
This Southwest deal was found by Cheapflights users on 1/27. 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.
Sat 4/256:05 pm
MDW
-
PDX
Nonstop4h 20m
Southwest
Sat 5/212:20 pm
PDX
-
MDW
1 stop14h 15m
Southwest
Deal found 1/27$223
This Delta deal was found by Cheapflights users on 1/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/171:49 pm
MDW
-
PDX
1 stop8h 41m
Delta
Thu 2/1912:40 am
PDX
-
MDW
1 stop6h 26m
Delta
Deal found 1/27$227
This Southwest deal was found by Cheapflights users on 1/27. 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.
Sun 5/39:45 pm
MDW
-
PDX
Nonstop4h 20m
Southwest
Sat 5/1611:55 pm
PDX
-
MDW
Nonstop3h 55m
Southwest
Deal found 1/27$232
This Delta deal was found by Cheapflights users on 1/28. 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.
Tue 2/171:49 pm
MDW
-
PDX
1 stop8h 41m
Delta
Wed 2/189:45 pm
PDX
-
MDW
1 stop10h 09m
Delta
Deal found 1/28$234
This Delta deal was found by Cheapflights users on 1/28. 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.
Fri 3/61:49 pm
MDW
-
PDX
1 stop8h 41m
Delta
Sat 3/712:05 am
PDX
-
MDW
1 stop5h 45m
Delta
Deal found 1/28$237
This Southwest deal was found by Cheapflights users on 1/28. 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.
Wed 5/136:45 am
MDW
-
PDX
1 stop9h 00m
Southwest
Fri 5/1511:55 pm
PDX
-
MDW
Nonstop3h 55m
Southwest
Deal found 1/28$241
This Southwest deal was found by Cheapflights users on 1/27. 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.
Sat 2/288:30 pm
MDW
-
PDX
Nonstop4h 30m
Southwest
Thu 3/58:55 pm
PDX
-
MDW
1 stop6h 50m
Southwest
Deal found 1/27$242
This Delta deal was found by Cheapflights users on 1/28. 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.
Tue 2/171:49 pm
MDW
-
PDX
1 stop8h 41m
Delta
Wed 2/2512:40 am
PDX
-
MDW
1 stop6h 26m
Delta
Deal found 1/28$244
This Southwest deal was found by Cheapflights users on 1/29. 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 7/85:30 pm
MDW
-
PDX
Nonstop4h 20m
Southwest
Wed 7/1511:30 pm
PDX
-
MDW
Nonstop3h 50m
Southwest
Deal found 1/29$245
This Southwest deal was found by Cheapflights users on 1/27. 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.
Tue 2/178:10 am
MDW
-
PDX
Nonstop4h 35m
Southwest
Thu 2/196:45 am
PDX
-
MDW
Nonstop3h 55m
Southwest
Deal found 1/27$247

Find flight deals from Midway to Oregon

Keep the following information in mind while searching for Midway to Oregon flight deals. Data was last updated January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$207
(Southwest)

One-way from

$92
(Kiwi.com)

Popular in

March

Cheapest in

September

Average price

$308

Good round-trip deal

$247 or less

Good one-way deal

$188 or less
Provider with most accurate pricing for Chicago (CHI)-Portland flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Portland flights.
Search Deals
From Chicago Midway to Oregon
Search Deals
One-way flight from Chicago Midway to Oregon
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($20 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals
Price to beat on a round-trip flight from Chicago Midway to Oregon.
Search Deals
Price to beat on a one-way flight from Chicago Midway to Oregon.
Search Deals

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 January 29, 2026.
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

Wed 2/25

3:35 pm-6:00 pm

Nonstop4h 25m

Portland

Wed 3/4

9:55 am-9:05 pm

1 stop9h 10m

$207

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Tue 2/17

8:10 am-10:45 am

Nonstop4h 35m

Portland

Wed 2/18

7:25 am-5:15 pm

1 stop7h 50m

$207

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Wed 3/25

2:05 pm-8:25 pm

1 stop8h 20m

Portland

Mon 4/6

12:30 am-8:50 am

1 stop6h 20m

$217

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Fri 4/24

9:50 pm-12:10 am

Nonstop4h 20m

Portland

Mon 4/27

11:55 pm-5:50 am

Nonstop3h 55m

$217

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Tue 3/31

2:05 pm-8:25 pm

1 stop8h 20m

Portland

Mon 4/6

11:15 pm-8:53 am

1 stop7h 38m

$227

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Mon 2/23

1:49 pm-8:30 pm

1 stop8h 41m

Portland

Sun 3/1

12:40 am-9:06 am

1 stop6h 26m

$237

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Tue 4/14

8:50 pm-11:10 pm

Nonstop4h 20m

Portland

Sat 4/18

11:55 pm-5:50 am

Nonstop3h 55m

$242

ChicagoMedford

MDW - MFR

MDWMFR

Chicago Midway

Tue 3/10

2:05 pm-10:49 pm

2 stops10h 44m

Medford

Wed 3/11

6:00 am-6:40 pm

2 stops10h 40m

$248

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Fri 5/8

3:05 pm-9:40 pm

1 stop8h 35m

Portland

Mon 5/11

5:10 am-11:05 am

Nonstop3h 55m

$252

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Mon 5/11

7:40 pm-12:55 am

1 stop7h 15m

Portland

Fri 5/15

11:55 pm-5:50 am

Nonstop3h 55m

$252

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/28

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, March is the cheapest month in which you can book a flight from Chicago Midway Airport to Oregon (average of $122). Flying from Chicago Midway Airport to Oregon in June is currently the most expensive (average of $379). 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 January 29, 2026.

It’s typically best to fly out from Chicago Midway Airport to Oregon in the evening. Doing so could potentially save you 16% on the flight price compared to flying at noon, which is usually more expensive.

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 January 29, 2026.
Read reviews from past customers who have flown Southwest 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
4,267 reviews

Overall

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,267 reviews
Southwest
8.0
Very good
4,267 reviews

Overall

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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 25m. Fly via Southwest or Delta 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 $283, our data indicates the cheapest price to be $107. The most popular route (Chicago Midway - Portland), is priced around $185.

  • 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, March is the cheapest month in which you can book a flight from Chicago Midway Airport to Oregon (average of $122). Flying from Chicago Midway Airport to Oregon in June is currently the most expensive (average of $379). 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 Newark flights
Midway to Atlanta flights

Top airline flying from Midway to Oregon

Discover the top airline 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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$247Average$418FlexibilityNo cancel feeOn-time63%

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