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$57+ Cheap flights from Midway (MDW) to Portland (PDX)

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 11/18. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PDX
Nov 5 — Nov 121
1 adult
Tue 11/5
Tue 11/12
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Cheap flight deals from Midway to Portland

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Portland (PDX). 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 October 31, 2024.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Popular in

October

Cheapest in

February

Round-trip from

$108
(Frontier)

One-way from

$57
(Trip.com)
Provider with most accurate pricing for Chicago Midway-Portland flight deals.
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Provider most trusted by Cheapflights users for Chicago Midway-Portland flights.
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High demand for flights, 46% potential price rise
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Best time to find cheap flights, 43% potential price drop
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From Chicago Midway to Portland
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One-way flight from Chicago Midway to Portland
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Find flight deals from Midway to Portland

Cheapest flights from Midway to Portland
Explore the most affordable flight options available from Midway to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 31, 2024.

This FlightHub deal was found by Cheapflights users on 10/30. 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.
Sat 11/24:19 pmMDW - PDX
1 stop9h 40mFrontier
Sun 11/106:05 amPDX - MDW
1 stop17h 28mFrontier
Deal found 10/30$180
This Southwest deal was found by Cheapflights users on 10/30. 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 12/136:55 pmMDW - PDX
Nonstop4h 30mSouthwest
Wed 1/89:00 amPDX - MDW
Nonstop3h 55mSouthwest
Deal found 10/30$234
This Delta deal was found by Cheapflights users on 10/30. 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 12/111:30 pmMDW - PDX
2 stops11h 59mDelta
Sat 12/1411:13 pmPDX - MDW
1 stop7h 45mDelta
Deal found 10/30$235
This Trip.com deal was found by Cheapflights users on 10/30. 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.
Sun 11/310:59 pmMDW - PDX
1 stop16h 07mMultiple Airlines
Tue 11/58:14 pmPDX - MDW
2 stops17h 36mMultiple Airlines
Deal found 10/30$414

Find flights from Midway to Portland within your budget

Customize your flight search to find flights from Midway to Portland 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 2,570,725 searches. Data last updated October 31, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Thu 11/7

1:17 pm-12:11 am

1 stop12h 54m

$89

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Thu 11/28

12:50 pm-3:20 pm

Nonstop4h 30m

$90

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Sat 12/7

9:38 am-7:02 pm

2 stops11h 24m

$117

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Wed 11/27

11:15 am-12:51 am

3 stops15h 36m

$346

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Fri 12/20

8:41 pm-12:34 pm

1 stop17h 53m

Portland

Sun 1/12

10:37 am-11:44 am

1 stop23h 07m

$182

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Fri 12/13

6:55 pm-9:25 pm

Nonstop4h 30m

Portland

Wed 1/8

9:00 am-2:55 pm

Nonstop3h 55m

$234

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Wed 12/11

1:30 pm-11:29 pm

2 stops11h 59m

Portland

Sat 12/14

11:13 pm-8:58 am

1 stop7h 45m

$235

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Thu 11/14

11:31 am-12:52 am

2 stops15h 21m

Portland

Tue 11/19

5:39 pm-8:45 am

1 stop13h 06m

$579

Flights are sorted by cheapest first

Deals found on 10/30

Compare providers for flights from Midway to Portland

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to Portland in October.
ProviderPrice AccuracyTrust Score*Cancellation Policy
ExpediaPrice Accuracy1 starTrust Score*3 starsCancellation PolicyAirline Policy
FlightHubPrice Accuracy3 starsTrust Score*3 starsCancellation PolicyAirline Policy
eDreamsPrice Accuracy3 starsTrust Score*3 starsCancellation PolicyAirline Policy

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago Midway Airport-Portland flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Portland flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Portland flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-Portland flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago Midway Airport-Portland flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Midway to Portland

Have a flexible travel schedule? Discover the best time to fly to Portland 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 Portland

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

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

Currently, October is the cheapest month in which you can book a flight from Chicago Midway Airport to Portland (average of $276). Flying from Chicago Midway Airport to Portland 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 PDX?

Find hourly flight availability from Midway to Portland. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 31, 2024.

One of the essential ways to save on airfare from Chicago Midway Airport to Portland is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight in the evening could potentially save you up to 54% on airfare.

Rainfall in Portland by month

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

In terms of precipitation, rainfall in Portland 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 Portland when rainfall is around 0.7 in.

Temperature in Portland by month

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

If weather is an important factor for your trip to Portland, 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 Portland

Get insights into the airlines that provide service to Portland. 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 Portland. Reviews last updated October 31, 2024.
Get a feel of what it's like to fly with Frontier, Southwest and Delta from Chicago to Portland by reading reviews from past customers. 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
5,116 reviews

Boarding

8.3

Crew

8.7

Food

7.2

Comfort

8.1

Entertainment

7.7

Overall

8.1

Reviews

1 / 10

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

Southwest
8.1
Very good
5,116 reviews
Southwest
8.1
Very good
5,116 reviews

Boarding

8.3

Crew

8.7

Food

7.2

Comfort

8.1

Entertainment

7.7

Overall

8.1

Reviews

1 / 10

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

Delta
8.0
Very good
8,835 reviews
Southwest
8.1
Very good
5,116 reviews

Boarding

8.3

Crew

8.7

Food

7.2

Comfort

8.1

Entertainment

7.7

Overall

8.1

Reviews

1 / 10

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

Frontier
6.1
Okay
3,580 reviews
Southwest
8.1
Very good
5,116 reviews

Boarding

8.3

Crew

8.7

Food

7.2

Comfort

8.1

Entertainment

7.7

Overall

8.1

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 Portland. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Portland from Chicago Midway?

    Most people fly into Portland (PDX) if they book a flight to Portland from Chicago Midway. On average, Portland has 0 inbound flights from Chicago Midway per day from 2 airlines. Portland is conveniently located just 6.0 mi from Portland’s city center.

  • Can I find flights from Chicago Midway Airport to Portland for under $200 on Cheapflights?

    Yes, there are multiple flights from Chicago Midway Airport to Portland for under $200. The cheapest flight booked recently is on Frontier for just $108, but on average you can expect to pay $192.

  • Are there nonstop flights from Chicago Midway Airport to Portland for under $300 on Cheapflights?

    Cheapflights has at least 1 direct flight from Chicago Midway Airport to Portland under $300. A good price for a nonstop flight from Chicago Midway Airport to Portland is less than $234.

  • Are there last-minute flights available from Chicago Midway Airport to Portland for under $200?

    There are currently 3+ open flights from Chicago Midway Airport to Portland within the next 7 days for less than $200.

  • What days are nonstop flights available from Chicago Midway Airport to Portland?

    You can find nonstop flights on the following days: Sunday, Monday, Tuesday, Friday.

  • How many flights depart from Chicago Midway Airport to Portland on average per day?

    On average 3 flights depart from Chicago Midway Airport to Portland per day.
    Afternoon (Noon - 6pm) - 33% of flight departures
    Evening (6pm - Midnight) - 67% of flight departures

  • How long is the flight from Chicago Midway Airport to Portland?

    Airlines like Frontier, Southwest, and Delta fly from Chicago Midway Airport to Portland in about 4h 30m. The time it takes to get you to your destination can typically vary by up to 8h 24m. The distance between Chicago Midway Airport and Portland is about 1756 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines flying from Chicago Midway Airport to Portland round-trip?

    According to our current data, Frontier ($108), Southwest ($234), and Delta ($235) offers the cheapest pricing from Chicago Midway Airport to Portland. Frontier is currently priced 67% below the average price you’ll pay for this route.

  • What are the cheapest airlines to fly from Chicago Midway Airport to Portland one-way?

    One-way options have recently been found by users for as low as $57 on Frontier. Other airlines that offer cheap prices include Southwest from $90 and Delta from $117 one-way.

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

    While on average a flight from Chicago Midway Airport to Portland is generally $299, our data shows the cheapest flight currently is $93. When looking at the most popular route, (Chicago Midway - Portland), you can expect to pay $118 for that flight.

  • What does MDW to PDX mean?

    This is defined as Chicago Midway Airport (MDW) and Portland Airport (PDX). Codes like Portland Airport are often used to just call airports uniquely.

  • Can I find deals for flights from Midway to Portland that include extra baggage allowance?

    The amount of baggage you can bring on your Midway to Portland flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Midway to Portland with specific airlines?

    Yes, Cheapflights allows you to browse and filter Midway to Portland flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Midway to Portland by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • Can I find deals for flights from Midway to Portland that allow pets onboard?

    Many airlines flying from Midway to Portland offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Midway to Portland?

    Yes, you can often find last-minute deals on Midway to Portland flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Chicago Midway Airport to Portland flight deals updated?

    The Chicago Midway Airport to Portland flight deals you see on this page were last updated on 10/30.

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

    Currently, October is the cheapest month in which you can book a flight from Chicago Midway Airport to Portland (average of $276). Flying from Chicago Midway Airport to Portland 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.

See more FAQs

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Top 2 airlines flying from Midway to Portland

Discover the top 2 airlines that operate flights from Midway to Portland. 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 2,570,725 searches. Data last updated October 31, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$125Average$216FlexibilityNo cancel feeOn-time62%
DeltaCheapest$292Average$467FlexibilityNo cancel feeOn-timeN/A
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