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$100+ 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 1/21. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PDX
dic. 23 — dic. 301
lun. 12/23
lun. 12/30
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 diciembre 18, 2024.

Round-trip from

$193
(FlightHub)

One-way from

$100
(Delta)
From Chicago Midway to Oregon
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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 diciembre 18, 2024.

This FlightHub deal was found by Cheapflights users on 12/16. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/2310:04 pmMDW - PDX
1 stop19h 40mFrontier
dom. 12/2910:46 amPDX - MDW
1 stop16h 47mFrontier
Deal found 12/16$383
This Delta deal was found by Cheapflights users on 12/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/314:50 pmMDW - BOI
1 stop8h 05mDelta
mar. 1/145:30 amBOI - MDW
1 stop6h 16mDelta
Deal found 12/18$439
This Southwest deal was found by Cheapflights users on 12/16. 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.
mar. 12/312:55 pmMDW - BOI
2 stops9h 00mSouthwest
lun. 1/63:30 pmBOI - MDW
1 stop6h 55mSouthwest
Deal found 12/16$468
This Southwest deal was found by Cheapflights users on 12/17. 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. 12/233:40 pmMDW - PDX
1 stop9h 45mSouthwest
mar. 12/3111:30 amPDX - MDW
Nonstop3h 55mSouthwest
Deal found 12/17$568
This Delta deal was found by Cheapflights users on 12/16. 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. 12/172:15 pmMDW - PDX
1 stop8h 15mDelta
mar. 12/316:20 amPDX - MDW
1 stop8h 51mDelta
Deal found 12/16$612
This Delta deal was found by Cheapflights users on 12/16. 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. 12/249:30 amMDW - EUG
2 stops11h 35mDelta
jue. 1/25:46 amEUG - MDW
2 stops9h 58mDelta
Deal found 12/16$728
This Southwest deal was found by Cheapflights users on 12/18. 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.
jue. 12/198:05 amMDW - EUG
1 stop11h 15mSouthwest
mié. 12/256:25 amEUG - MDW
2 stops12h 15mSouthwest
Deal found 12/18$741
This Delta deal was found by Cheapflights users on 12/16. 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.
jue. 12/1912:10 pmMDW - RDM
2 stops12h 42mDelta
sáb. 12/215:00 amRDM - MDW
2 stops10h 44mDelta
Deal found 12/16$1,117

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 diciembre 18, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

mié. 1/22

8:15 am-12:07 am

1 stop17h 52m

Portland

mar. 3/18

10:06 am-12:17 am

1 stop12h 11m

$193

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

lun. 1/13

1:26 pm-8:35 pm

1 stop9h 09m

Portland

mar. 1/21

12:45 am-9:39 am

1 stop6h 54m

$208

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

jue. 1/16

8:10 pm-10:40 pm

Nonstop4h 30m

Portland

jue. 1/30

9:00 am-2:55 pm

Nonstop3h 55m

$218

ChicagoBoise

MDW - BOI

MDWBOI

Chicago Midway

vie. 1/31

6:59 pm-11:58 pm

1 stop5h 59m

Boise Air Term. Gowen Fld

vie. 2/7

5:30 am-12:42 pm

1 stop6h 12m

$248

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

jue. 1/9

7:15 am-10:17 pm

2 stops17h 02m

Portland

mié. 1/15

8:00 am-12:13 am

3 stops14h 13m

$288

ChicagoEugene

MDW - EUG

MDWEUG

Chicago Midway

mié. 1/22

8:15 am-4:00 pm

2 stops33h 45m

Eugene

dom. 1/26

4:50 pm-11:44 am

1 stop16h 54m

$291

ChicagoMedford

MDW - MFR

MDWMFR

Chicago Midway

mié. 1/22

8:15 am-10:10 am

2 stops27h 55m

Medford

dom. 1/26

8:44 pm-11:44 am

1 stop13h 00m

$294

ChicagoMedford

MDW - MFR

MDWMFR

Chicago Midway

mié. 1/15

1:26 pm-11:06 pm

2 stops11h 40m

Medford

mar. 1/21

5:50 am-5:47 pm

2 stops9h 57m

$335

ChicagoRedmond

MDW - RDM

MDWRDM

Chicago Midway

vie. 1/31

2:08 pm-11:52 pm

2 stops11h 44m

Bend/Redmond

vie. 2/7

6:20 am-5:43 pm

2 stops9h 23m

$338

ChicagoBoise

MDW - BOI

MDWBOI

Chicago Midway

vie. 2/21

5:20 am-10:25 am

1 stop6h 05m

Boise Air Term. Gowen Fld

mar. 2/25

11:50 am-9:45 pm

1 stop8h 55m

$348

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/18

Showing 1-10 of 23 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 $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 diciembre 18, 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 diciembre 18, 2024.
Read through reviews of airlines operating flights from Chicago to Oregon, such as Delta, Frontier 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
4,848 reviews

Crew

8.7

Food

7.2

Comfort

8.1

Entertainment

7.7

Boarding

8.2

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,848 reviews
Southwest
8.1
Very good
4,848 reviews

Crew

8.7

Food

7.2

Comfort

8.1

Entertainment

7.7

Boarding

8.2

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,604 reviews
Southwest
8.1
Very good
4,848 reviews

Crew

8.7

Food

7.2

Comfort

8.1

Entertainment

7.7

Boarding

8.2

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Frontier
6.1
Okay
3,479 reviews
Southwest
8.1
Very good
4,848 reviews

Crew

8.7

Food

7.2

Comfort

8.1

Entertainment

7.7

Boarding

8.2

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 ($100), Southwest ($109), and Frontier ($124).

  • 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 $301, our data indicates the cheapest price to be $150. The most popular route (Chicago Midway - Portland), is priced around $208.

  • 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.

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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 2,558,603 searches. Data last updated diciembre 18, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$118Average$191FlexibilityNo cancel feeOn-time62%
DeltaCheapest$236Average$597FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$237Average$420FlexibilityNo cancel feeOn-time63%
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