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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 3/1. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PDX
Nov 25 — Dec 21
Mon 11/25
Mon 12/2
1 adult, Economy
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Cheap flight deals from Midway to Oregon

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Oregon (USOR). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated November 20, 2024.

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 November 20, 2024.

This Frontier deal was found by Cheapflights users on 11/19. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/217:00 amMDW - PDX
1 stop10h 44mFrontier
Sat 1/47:06 pmPDX - MDW
1 stop12h 43mFrontier
Deal found 11/19$208
This Delta deal was found by Cheapflights users on 11/20. 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.
Tue 12/314:50 pmMDW - BOI
1 stop8h 05mDelta
Tue 1/145:30 amBOI - MDW
1 stop6h 16mDelta
Deal found 11/20$248
This eDestinos deal was found by Cheapflights users on 11/19. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/198:41 pmMDW - PDX
1 stop23h 41mMultiple Airlines
Thu 12/267:19 pmPDX - MDW
2 stops22h 15mMultiple Airlines
Deal found 11/19$334
This Southwest deal was found by Cheapflights users on 11/19. 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.
Wed 12/117:40 pmMDW - PDX
Nonstop4h 30mSouthwest
Sun 12/156:25 amPDX - MDW
Nonstop3h 55mSouthwest
Deal found 11/19$344
This Delta deal was found by Cheapflights users on 11/20. 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.
Thu 12/121:30 pmMDW - PDX
2 stops11h 59mDelta
Mon 12/1611:13 pmPDX - MDW
1 stop7h 45mDelta
Deal found 11/20$375
This Delta deal was found by Cheapflights users on 11/20. 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.
Mon 12/162:15 pmMDW - EUG
2 stops10h 43mDelta
Wed 12/256:25 amEUG - MDW
2 stops8h 46mDelta
Deal found 11/20$384
This Southwest deal was found by Cheapflights users on 11/18. 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.
Wed 12/43:25 pmMDW - BOI
1 stop8h 30mSouthwest
Sun 12/222:55 pmBOI - MDW
1 stop8h 55mSouthwest
Deal found 11/18$403
This Southwest deal was found by Cheapflights users on 11/19. 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.
Wed 12/1811:30 amMDW - EUG
2 stops10h 40mSouthwest
Wed 12/251:20 pmEUG - MDW
1 stop7h 05mSouthwest
Deal found 11/19$416
This Delta deal was found by Cheapflights users on 11/19. 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.
Sat 12/79:30 amMDW - RDM
2 stops11h 18mDelta
Tue 12/106:05 amRDM - MDW
2 stops10h 27mDelta
Deal found 11/19$460
This Delta deal was found by Cheapflights users on 11/19. 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 12/182:15 pmMDW - MFR
2 stops10h 57mDelta
Wed 12/255:05 amMFR - MDW
2 stops9h 05mDelta
Deal found 11/19$560
This Mytrip deal was found by Cheapflights users on 11/18. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/47:55 pmMDW - BOI
3 stops40h 03mMultiple Airlines
Sun 12/2211:57 amBOI - MDW
2 stops19h 33mMultiple Airlines
Deal found 11/18$931

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 2,629,791 searches. Data last updated November 20, 2024.

Fly from

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Fly to

Any airport

Route

Depart

Return

Price

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Mon 2/17

6:40 am-12:37 am

1 stop19h 57m

Portland

Wed 2/19

6:32 am-12:17 am

1 stop15h 45m

$188

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Mon 1/13

12:43 pm-8:46 pm

1 stop10h 03m

Portland

Thu 1/16

12:03 pm-12:17 am

1 stop10h 14m

$204

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Wed 2/19

1:26 pm-5:35 pm

1 stop6h 09m

Portland

Fri 2/21

12:45 am-10:36 am

1 stop7h 51m

$216

ChicagoBoise

MDW - BOI

MDWBOI

Chicago Midway

Tue 12/31

4:50 pm-11:55 pm

1 stop8h 05m

Boise Air Term. Gowen Fld

Tue 1/14

5:30 am-12:46 pm

1 stop6h 16m

$248

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Tue 2/18

8:10 pm-10:40 pm

Nonstop4h 30m

Portland

Sat 2/22

6:35 am-12:30 pm

Nonstop3h 55m

$253

ChicagoMedford

MDW - MFR

MDWMFR

Chicago Midway

Thu 1/30

9:34 am-4:42 pm

2 stops9h 08m

Medford

Sat 2/1

5:45 am-4:12 pm

2 stops8h 27m

$316

ChicagoRedmond

MDW - RDM

MDWRDM

Chicago Midway

Fri 1/24

9:34 am-4:46 pm

2 stops9h 12m

Bend/Redmond

Sun 1/26

5:55 am-5:47 pm

2 stops9h 52m

$336

ChicagoBoise

MDW - BOI

MDWBOI

Chicago Midway

Fri 1/10

6:20 am-11:15 am

1 stop5h 55m

Boise Air Term. Gowen Fld

Mon 1/13

12:20 pm-11:20 pm

1 stop10h 00m

$348

ChicagoEugene

MDW - EUG

MDWEUG

Chicago Midway

Wed 1/8

1:26 pm-11:52 pm

2 stops12h 26m

Eugene

Mon 1/13

5:47 am-6:14 pm

2 stops10h 27m

$352

ChicagoEugene

MDW - EUG

MDWEUG

Chicago Midway

Wed 12/18

11:30 am-8:10 pm

2 stops10h 40m

Eugene

Wed 12/25

1:20 pm-10:25 pm

1 stop7h 05m

$416

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/20

Showing 1-10 of 22 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.

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 $268). Flying from Chicago Midway Airport to Oregon in July is currently the most expensive (average of $341). 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 November 20, 2024.

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 November 20, 2024.
Read through reviews of airlines operating flights from Chicago to Oregon, such as Frontier, Delta and Southwest. 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
5,014 reviews

Boarding

8.2

Overall

8.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Southwest
8.1
Very good
5,014 reviews
Southwest
8.1
Very good
5,014 reviews

Boarding

8.2

Overall

8.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Delta
8.0
Very good
8,756 reviews
Southwest
8.1
Very good
5,014 reviews

Boarding

8.2

Overall

8.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Frontier
6.1
Okay
3,539 reviews
Southwest
8.1
Very good
5,014 reviews

Boarding

8.2

Overall

8.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

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 ($93), Southwest ($99), and Delta ($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 - Medford 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 $325, our data indicates the cheapest price to be $122. The most popular route (Chicago Midway - Portland), is priced around $179.

  • 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 $268). Flying from Chicago Midway Airport to Oregon in July is currently the most expensive (average of $341). 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 3 airlines flying from Midway to Oregon

Discover the top 3 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 2,629,791 searches. Data last updated November 20, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$118Average$187FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$237Average$420FlexibilityNo cancel feeOn-time63%
DeltaCheapest$292Average$597FlexibilityNo cancel feeOn-timeN/A
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