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$96+ 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 3/1. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PDX
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
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 February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$228
(Trip.com)

One-way from

$96
(Frontier)

Popular in

December

Cheapest in

September

Average price

$333

Good round-trip deal

$288 or less

Good one-way deal

$118 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. 4% potential increase in price ($15 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 February 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 February 20, 2025.

This Trip.com deal was found by Cheapflights users on 2/20. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/18:44 pmMDW - PDX
1 stop13h 56mFrontier
Wed 3/56:32 amPDX - MDW
1 stop15h 45mFrontier
Deal found 2/20$228
This Delta deal was found by Cheapflights users on 2/20. 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 4/267:00 pmMDW - BOI
1 stop5h 59mDelta
Tue 4/295:30 amBOI - MDW
1 stop7h 52mDelta
Deal found 2/20$229
This Delta deal was found by Cheapflights users on 2/19. 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.
Wed 3/129:54 amMDW - PDX
1 stop10h 07mDelta
Tue 3/186:35 amPDX - MDW
1 stop5h 40mDelta
Deal found 2/19$237
This Southwest deal was found by Cheapflights users on 2/19. 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 4/154:35 pmMDW - PDX
1 stop8h 35mSouthwest
Tue 4/226:35 pmPDX - MDW
1 stop8h 45mSouthwest
Deal found 2/19$257
This Delta deal was found by Cheapflights users on 2/19. 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 4/89:23 amMDW - RDM
2 stops9h 32mDelta
Tue 4/155:36 pmRDM - MDW
2 stops13h 04mDelta
Deal found 2/19$304
This Southwest deal was found by Cheapflights users on 2/18. 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 3/45:40 pmMDW - BOI
1 stop6h 05mSouthwest
Mon 3/107:55 pmBOI - MDW
1 stop8h 25mSouthwest
Deal found 2/18$309
This Delta deal was found by Cheapflights users on 2/19. 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 4/221:16 pmMDW - MFR
2 stops11h 50mDelta
Fri 4/255:30 pmMFR - MDW
2 stops13h 10mDelta
Deal found 2/19$327
This Southwest deal was found by Cheapflights users on 2/19. 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.
Mon 8/117:10 amMDW - EUG
1 stop7h 30mSouthwest
Sat 8/162:25 pmEUG - MDW
1 stop6h 40mSouthwest
Deal found 2/19$427
This Delta deal was found by Cheapflights users on 2/20. 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 5/91:00 pmMDW - EUG
2 stops12h 17mDelta
Tue 5/135:15 amEUG - MDW
2 stops11h 15mDelta
Deal found 2/20$462

Find flights from Midway to Oregon within your budget

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 February 20, 2025.

Fly from

Midway

Fly to

Oregon

Route

Depart

Return

Price

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Sat 4/5

8:59 pm-8:47 am

1 stop13h 48m

Portland

Sat 4/12

6:40 am-12:21 am

1 stop15h 41m

$228

ChicagoBoise

MDW - BOI

MDWBOI

Chicago Midway

Sat 4/26

7:00 pm-11:59 pm

1 stop5h 59m

Boise Air Term. Gowen Fld

Tue 4/29

5:30 am-2:22 pm

1 stop7h 52m

$229

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Wed 3/12

9:54 am-6:01 pm

1 stop10h 07m

Portland

Tue 3/18

6:35 am-2:15 pm

1 stop5h 40m

$237

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Tue 4/15

4:35 pm-11:10 pm

1 stop8h 35m

Portland

Tue 4/22

6:35 pm-5:20 am

1 stop8h 45m

$257

ChicagoRedmond

MDW - RDM

MDWRDM

Chicago Midway

Tue 4/8

9:23 am-4:55 pm

2 stops9h 32m

Bend/Redmond

Tue 4/15

5:36 pm-8:40 am

2 stops13h 04m

$304

ChicagoBoise

MDW - BOI

MDWBOI

Chicago Midway

Tue 3/4

5:40 pm-10:45 pm

1 stop6h 05m

Boise Air Term. Gowen Fld

Mon 3/10

7:55 pm-5:20 am

1 stop8h 25m

$309

ChicagoMedford

MDW - MFR

MDWMFR

Chicago Midway

Tue 4/22

1:16 pm-11:06 pm

2 stops11h 50m

Medford

Fri 4/25

5:30 pm-8:40 am

2 stops13h 10m

$327

ChicagoEugene

MDW - EUG

MDWEUG

Chicago Midway

Mon 8/11

7:10 am-12:40 pm

1 stop7h 30m

Eugene

Sat 8/16

2:25 pm-11:05 pm

1 stop6h 40m

$427

ChicagoEugene

MDW - EUG

MDWEUG

Chicago Midway

Fri 5/9

1:00 pm-11:17 pm

2 stops12h 17m

Eugene

Tue 5/13

5:15 am-6:30 pm

2 stops11h 15m

$462

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Sat 3/1

8:44 pm-8:40 am

1 stop13h 56m

$96

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/19

Showing 1-10 of 20 results
1
2

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.

Travel insights for flights from Midway to Oregon

Get recent, data-driven insights about flights from Midway to Oregon including ideal travel times, pricing trends, and more.

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 $376). 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 February 20, 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 February 20, 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
8.1
Very good
4,411 reviews

Food

7.1

Boarding

8.2

Overall

8.1

Entertainment

7.6

Comfort

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Boarding

8.2

Overall

8.1

Entertainment

7.6

Comfort

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,219 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Boarding

8.2

Overall

8.1

Entertainment

7.6

Comfort

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Allegiant Air
7.3
Good
765 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Boarding

8.2

Overall

8.1

Entertainment

7.6

Comfort

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Frontier
6.0
Okay
3,355 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Boarding

8.2

Overall

8.1

Entertainment

7.6

Comfort

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 Frontier ($96), Southwest ($109), and Delta ($115).

  • 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 $339, our data indicates the cheapest price to be $98. The most popular route (Chicago Midway - Portland), is priced around $109.

  • 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 $376). 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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$108Average$202FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$228Average$431FlexibilityNo cancel feeOn-time63%
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