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$100+ Cheap flights from Oregon to Midway (MDW)

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 1/15. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — MDW
Dec 24 — Dec 311
Tue 12/24
Tue 12/31
1 adult, Economy
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Cheap flight deals from Oregon to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Oregon (USOR) to Midway (MDW). 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 December 19, 2024.

Round-trip from

$228
(Delta)

One-way from

$100
(Delta)
From Oregon to Chicago Midway
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One-way flight from Oregon to Chicago Midway
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Find flight deals from Oregon to Midway

Cheapest flights from Oregon to Midway
Explore the most affordable flight options available from Oregon to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 19, 2024.

This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/301:05 pmPDX - MDW
1 stop6h 04mFrontier
Sun 1/58:41 pmMDW - PDX
1 stop23h 18mFrontier
Deal found 12/18$325
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.
Mon 12/304:35 pmPDX - MDW
1 stop7h 05mSouthwest
Sun 1/56:50 pmMDW - PDX
Nonstop4h 30mSouthwest
Deal found 12/18$518
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.
Fri 12/204:50 pmBOI - MDW
1 stop7h 50mSouthwest
Sun 12/229:30 amMDW - BOI
1 stop9h 50mSouthwest
Deal found 12/16$598
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/225:32 amBOI - MDW
2 stops9h 52mDelta
Wed 12/256:00 amMDW - BOI
1 stop8h 14mDelta
Deal found 12/17$673
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.
Mon 12/3010:05 pmPDX - MDW
1 stop9h 18mDelta
Sat 1/49:30 amMDW - PDX
2 stops11h 14mDelta
Deal found 12/18$960
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.
Sun 12/225:05 amMFR - MDW
2 stops10h 39mDelta
Wed 12/259:30 amMDW - MFR
2 stops11h 50mDelta
Deal found 12/18$1,018
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.
Tue 12/311:20 pmEUG - MDW
1 stop7h 05mSouthwest
Sat 1/48:05 amMDW - EUG
1 stop11h 10mSouthwest
Deal found 12/18$1,110
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.
Sun 12/225:46 amEUG - MDW
2 stops9h 58mDelta
Fri 12/2712:10 pmMDW - EUG
2 stops12h 48mDelta
Deal found 12/18$1,910

Find flights from Oregon to Midway within your budget

Customize your flight search to find flights from Oregon to Midway 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 December 19, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

BoiseChicago

BOI - MDW

BOIMDW

Boise Air Term. Gowen Fld

Wed 1/22

5:30 am-12:46 pm

1 stop6h 16m

Chicago Midway

Mon 1/27

6:59 pm-11:58 pm

1 stop5h 59m

$228

PortlandChicago

PDX - MDW

PDXMDW

Portland

Wed 1/15

9:00 am-2:55 pm

Nonstop3h 55m

Chicago Midway

Wed 1/22

8:30 am-10:55 am

Nonstop4h 25m

$233

PortlandChicago

PDX - MDW

PDXMDW

Portland

Wed 1/22

12:45 am-9:39 am

1 stop6h 54m

Chicago Midway

Mon 1/27

1:26 pm-8:35 pm

1 stop9h 09m

$236

PortlandChicago

PDX - MDW

PDXMDW

Portland

Sun 3/2

6:32 am-12:17 am

1 stop15h 45m

Chicago Midway

Thu 3/6

8:44 pm-8:40 am

1 stop13h 56m

$238

PortlandChicago

PDX - MDW

PDXMDW

Portland

Mon 2/10

5:30 pm-12:17 am

2 stops28h 47m

Chicago Midway

Sat 2/22

10:26 am-9:21 am

3 stops24h 55m

$240

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Sat 1/18

5:15 am-5:47 pm

2 stops10h 32m

Chicago Midway

Fri 1/24

1:26 pm-11:52 pm

2 stops12h 26m

$270

BoiseChicago

BOI - MDW

BOIMDW

Boise Air Term. Gowen Fld

Thu 2/6

2:50 pm-11:05 pm

1 stop7h 15m

Chicago Midway

Thu 8/7

1:05 pm-3:50 pm

Nonstop3h 45m

$374

EugeneChicago

EUG - MDW

EUGMDW

Eugene

Tue 1/7

5:00 am-5:47 pm

2 stops10h 47m

Chicago Midway

Fri 1/10

1:26 pm-10:47 pm

2 stops11h 21m

$486

MedfordChicago

MFR - MDW

MFRMDW

Medford

Sat 1/11

5:00 am-5:47 pm

2 stops10h 47m

Chicago Midway

Fri 1/17

1:26 pm-11:06 pm

2 stops11h 40m

$498

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Fri 1/31

5:59 pm-10:36 am

3 stops14h 37m

Chicago Midway

Fri 2/7

12:43 pm-10:39 pm

2 stops11h 56m

$556

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

Showing 1-10 of 22 results
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Best time to book a flight from Oregon to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Oregon 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 Oregon to Midway

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

What is the cheapest month to book a flight from Oregon to Chicago Midway Airport?

Currently, April is the cheapest month in which you can book a flight from Oregon to Chicago Midway Airport (average of $160). Flying from Oregon to Chicago Midway Airport in October is currently the most expensive (average of $232). 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 OR to MDW?

Find hourly flight availability from Oregon to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 19, 2024.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Oregon to Chicago Midway Airport as you normally would.

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, 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 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated December 19, 2024.
See what other customers who have flown with Delta, Southwest and Frontier from Oregon to Chicago have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,836 reviews

Entertainment

7.7

Food

7.2

Crew

8.7

Boarding

8.2

Comfort

8.1

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
4,836 reviews
Southwest
8.1
Very good
4,836 reviews

Entertainment

7.7

Food

7.2

Crew

8.7

Boarding

8.2

Comfort

8.1

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
8,600 reviews
Southwest
8.1
Very good
4,836 reviews

Entertainment

7.7

Food

7.2

Crew

8.7

Boarding

8.2

Comfort

8.1

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.

Allegiant Air
7.4
Good
829 reviews
Southwest
8.1
Very good
4,836 reviews

Entertainment

7.7

Food

7.2

Crew

8.7

Boarding

8.2

Comfort

8.1

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
3,478 reviews
Southwest
8.1
Very good
4,836 reviews

Entertainment

7.7

Food

7.2

Crew

8.7

Boarding

8.2

Comfort

8.1

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 Oregon to Midway. 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 Oregon to Chicago Midway Airport one-way?

    $100 is the cheapest one-way deal found within the past few days, from Delta. You may also be able to find cheap deals on Southwest and Frontier, with prices starting from $125 and $130, respectively.

  • What are the most popular routes from Oregon to Chicago Midway Airport?

    When deciding which route to take from Oregon to Chicago Midway Airport consider Portland - Chicago Midway, Boise Air Term. Gowen Fld - Chicago Midway or Eugene - Chicago Midway as they are the most popular.

  • What are the cheapest flights from Oregon to Chicago Midway Airport?

    Looking at all options, your cheapest flight can be booked for $198. While the most popular route (Portland - Chicago Midway) can be booked for $180 on average our data indicates $394 when flying from Oregon to Chicago Midway Airport.

  • Can I find deals for flights from Oregon to Midway that include hotel bookings?

    Yes. In addition to deals on Oregon to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Oregon to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Oregon to Midway.

  • Can I find deals for business class flights from Oregon to Midway?

    Yes. Cheapflights offers flight deals from Oregon to Midway 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 Oregon to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Oregon to Chicago Midway Airport (average of $160). Flying from Oregon to Chicago Midway Airport in October is currently the most expensive (average of $232). 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 Oregon to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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Top 3 airlines flying from Oregon to Midway

Discover the top 3 airlines that operate flights from Oregon to Midway. 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 December 19, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$134Average$284FlexibilityNo cancel feeOn-time62%
DeltaCheapest$216Average$455FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$233Average$551FlexibilityNo cancel feeOn-time63%
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