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Midway

$99+ Cheap flights from Portland, ME (PWM) 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 4/23. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MDW
kwi 2 — kwi 91
czw. 4/2
czw. 4/9
1 adult, Economy
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Cheap flight deals from Portland to Midway

Cheapest flights from Portland to Midway
Explore the most affordable flight options available from Portland to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on Marzec 3, 2026.

This Delta deal was found by Cheapflights users on 2/26. 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.
śr. 4/86:03 am
PWM
-
MDW
2 stops7h 26m
Delta
pt. 4/101:10 pm
MDW
-
PWM
2 stops9h 12m
Delta
Deal found 2/26$214
This Southwest deal was found by Cheapflights users on 3/3. 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.
wt. 4/71:00 pm
PWM
-
MDW
1 stop7h 30m
Southwest
sob. 4/116:10 am
MDW
-
PWM
1 stop4h 45m
Southwest
Deal found 3/3$229
This Delta deal was found by Cheapflights users on 2/26. 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.
śr. 4/112:51 pm
PWM
-
MDW
1 stop6h 03m
Delta
pon. 4/61:10 pm
MDW
-
PWM
2 stops9h 02m
Delta
Deal found 2/26$234
This Southwest deal was found by Cheapflights users on 2/26. 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.
wt. 5/56:10 am
PWM
-
MDW
2 stops8h 55m
Southwest
wt. 5/125:00 pm
MDW
-
PWM
1 stop4h 35m
Southwest
Deal found 2/26$240
This Southwest deal was found by Cheapflights users on 2/27. 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.
czw. 6/47:40 am
PWM
-
MDW
Nonstop2h 35m
Southwest
ndz. 6/77:55 pm
MDW
-
PWM
Nonstop2h 15m
Southwest
Deal found 2/27$249
This Southwest deal was found by Cheapflights users on 3/3. 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.
pon. 3/232:50 pm
PWM
-
MDW
2 stops6h 20m
Southwest
czw. 3/266:35 am
MDW
-
PWM
1 stop4h 20m
Southwest
Deal found 3/3$254
This Delta deal was found by Cheapflights users on 3/3. 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.
wt. 4/76:03 am
PWM
-
MDW
2 stops7h 26m
Delta
sob. 4/111:10 pm
MDW
-
PWM
2 stops9h 12m
Delta
Deal found 3/3$259
This Southwest deal was found by Cheapflights users on 3/1. 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.
sob. 5/24:35 pm
PWM
-
MDW
1 stop5h 05m
Southwest
pon. 5/42:10 pm
MDW
-
PWM
2 stops8h 15m
Southwest
Deal found 3/1$261
This Southwest deal was found by Cheapflights users on 2/27. 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.
śr. 7/157:30 am
PWM
-
MDW
Nonstop2h 35m
Southwest
sob. 7/181:10 pm
MDW
-
PWM
1 stop6h 50m
Southwest
Deal found 2/27$268
This Delta deal was found by Cheapflights users on 3/3. 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.
śr. 9/212:50 pm
PWM
-
MDW
1 stop6h 41m
Delta
śr. 9/96:00 am
MDW
-
PWM
1 stop5h 22m
Delta
Deal found 3/3$269

Find flight deals from Portland to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Portland (PWM) 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 Marzec 3, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$229
(Southwest)

One-way from

$99
(Delta)

Popular in

January

Cheapest in

February

Average price

$403

Good round-trip deal

$482 or less

Good one-way deal

$218 or less
Provider with most accurate pricing for Portland-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Portland-Chicago Midway flights.
Search Deals
From Portland to Chicago Midway
Search Deals
One-way flight from Portland to Chicago Midway
Search Deals
High demand for flights, 5% potential price rise
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
Search Deals
Price to beat on a round-trip flight from Portland to Chicago Midway.
Search Deals
Price to beat on a one-way flight from Portland to Chicago Midway.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Portland 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 Marzec 3, 2026.
Use the filters below to find and compare flights from Portland to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

PortlandChicago

PWM - MDW

PWMMDW

Portland

pt. 5/1

4:50 pm-10:20 pm

1 stop6h 30m

Chicago Midway

pon. 5/4

2:10 pm-11:25 pm

2 stops8h 15m

$279

PortlandChicago

PWM - MDW

PWMMDW

Portland

śr. 4/8

3:55 pm-7:30 pm

1 stop4h 35m

Chicago Midway

pt. 4/10

9:00 am-2:10 pm

1 stop4h 10m

$292

PortlandChicago

PWM - MDW

PWMMDW

Portland

wt. 4/14

6:10 am-1:30 pm

2 stops8h 20m

Chicago Midway

czw. 4/16

12:50 pm-11:25 pm

2 stops9h 35m

$323

PortlandChicago

PWM - MDW

PWMMDW

Portland

pt. 5/1

4:50 pm-10:20 pm

1 stop6h 30m

Chicago Midway

pt. 5/8

2:10 pm-11:25 pm

2 stops8h 15m

$351

PortlandChicago

PWM - MDW

PWMMDW

Portland

śr. 4/29

3:55 pm-7:30 pm

1 stop4h 35m

Chicago Midway

ndz. 5/3

7:55 am-4:50 pm

2 stops7h 55m

$353

PortlandChicago

PWM - MDW

PWMMDW

Portland

sob. 3/7

5:20 pm-12:05 am

2 stops7h 45m

Chicago Midway

pon. 3/9

5:00 pm-12:05 am

1 stop6h 05m

$363

PortlandChicago

PWM - MDW

PWMMDW

Portland

czw. 4/23

12:46 pm-5:58 pm

1 stop6h 12m

$99

PortlandChicago

PWM - MDW

PWMMDW

Portland

śr. 4/29

12:46 pm-5:58 pm

1 stop6h 12m

$99

PortlandChicago

PWM - MDW

PWMMDW

Portland

pt. 4/24

12:46 pm-5:58 pm

1 stop6h 12m

$106

PortlandChicago

PWM - MDW

PWMMDW

Portland

czw. 5/28

12:55 pm-6:33 pm

1 stop6h 38m

$115

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/26

Showing 1-10 of 16 resultsSorted by cheapest first
1
2

Compare providers for flights from Portland to Midway

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 Portland to Midway in March.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*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 Portland, Maine-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Portland, Maine-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Portland, Maine-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Portland, Maine-Chicago Midway Airport 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 Portland, Maine-Chicago Midway Airport 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 Portland to Midway

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

Cheapflights Insights

Everything you need to know about your flight from Portland to Chicago Midway Airport

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

Currently, June is the cheapest month in which you can book a flight from Portland, Maine to Chicago Midway Airport (average of $97). Flying from Portland, Maine to Chicago Midway Airport in April is currently the most expensive (average of $167). 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 PWM to MDW?

Find hourly flight availability from Portland 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 Marzec 3, 2026.

One of the essential ways to save on airfare from Portland, Maine to Chicago Midway Airport is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight in the morning could potentially save you up to 9% on airfare.

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 Marzec 3, 2026.
See what other customers who have flown with Southwest from Portland to Chicago Midway Airport have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,302 reviews

Overall

8.0

Boarding

8.1

Crew

8.6

Comfort

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Feb 2026

DEN - BDL

Weird they cancelled a direct and rerouted me on a connecting flight to get in 10 hours later. What was the point? Crew and flight were great, but not sure what's going on with Southwest.
Southwest
8.0
Very good
4,302 reviews
Southwest
8.0
Very good
4,302 reviews

Overall

8.0

Boarding

8.1

Crew

8.6

Comfort

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Feb 2026

DEN - BDL

Weird they cancelled a direct and rerouted me on a connecting flight to get in 10 hours later. What was the point? Crew and flight were great, but not sure what's going on with Southwest.

Related info for your journey

Find useful and relevant information for your journey from Portland to Midway. 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 from for flights from Portland to Chicago Midway?

    For a flight from Portland to Chicago Midway, you will be flying from Portland. Portland (PWM) is just 2.9 mi from the center of the city. Portland is the only Portland airport and it handles 0 outbound flights to Chicago Midway per day. 1 airline has flights to Chicago Midway from Portland on a regular basis.

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

    Airlines like Southwest fly from Portland, Maine to Chicago Midway Airport in about 6h 30m. The time it takes to get you to your destination can typically vary by up to . Airlines will cover a distance of 892 mi.

  • What is the cheapest airline to fly from Portland, Maine to Chicago Midway Airport round-trip?

    Southwest, at $246, was found to be the cheapest airline from Portland, Maine to Chicago Midway Airport.. This flight start at 30% lower than the current average price 3 months from now.

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

    While on average a flight from Portland, Maine to Chicago Midway Airport is generally $420, our data shows the cheapest flight currently is $179. When looking at the most popular route, (Portland - Chicago Midway), you can expect to pay $249 for that flight.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Portland 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 Portland, Maine to Chicago Midway Airport?

    Currently, June is the cheapest month in which you can book a flight from Portland, Maine to Chicago Midway Airport (average of $97). Flying from Portland, Maine to Chicago Midway Airport in April is currently the most expensive (average of $167). 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

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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Alternative routes for Portland to Midway

See prices for flight routes from nearby airports that may be better suited for you.
Boston to O'Hare Intl flights
Boston to Midway flights
Portland to O'Hare Intl flights
Boston to Rockford flights
Bangor to O'Hare Intl flights

Top airline flying from Portland to Midway

Discover the top airline that operate flights from Portland 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 Marzec 3, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$246Average$387FlexibilityNo cancel feeOn-time63%

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