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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 8/25. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MDW
Jun 29 — Jul 61
Mon 6/29
Mon 7/6
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 May 30, 2026.

This Southwest deal was found by Cheapflights users on 5/29. 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 9/165:45 am
PWM
-
MDW
2 stops7h 05m
Southwest
Sat 9/199:55 am
MDW
-
PWM
2 stops10h 05m
Southwest
Deal found 5/29$270
This Southwest deal was found by Cheapflights users on 5/25. 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 7/17:30 am
PWM
-
MDW
Nonstop2h 35m
Southwest
Sat 7/47:40 am
MDW
-
PWM
Nonstop2h 15m
Southwest
Deal found 5/25$287
This Southwest deal was found by Cheapflights users on 5/27. 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.
Fri 7/37:40 am
PWM
-
MDW
Nonstop2h 35m
Southwest
Tue 7/76:15 pm
MDW
-
PWM
Nonstop2h 20m
Southwest
Deal found 5/27$292
This Southwest deal was found by Cheapflights users on 5/28. 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 9/27:45 am
PWM
-
MDW
Nonstop2h 35m
Southwest
Wed 9/96:50 pm
MDW
-
PWM
Nonstop2h 15m
Southwest
Deal found 5/28$297
This Delta deal was found by Cheapflights users on 5/25. 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 7/112:40 pm
PWM
-
MDW
1 stop6h 51m
Delta
Fri 7/31:26 pm
MDW
-
PWM
2 stops8h 34m
Delta
Deal found 5/25$312
This Southwest deal was found by Cheapflights users on 5/26. 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.
Sat 9/53:40 pm
PWM
-
MDW
Nonstop2h 35m
Southwest
Mon 9/76:10 pm
MDW
-
PWM
Nonstop2h 20m
Southwest
Deal found 5/26$313
This Southwest deal was found by Cheapflights users on 5/28. 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 7/155:30 am
PWM
-
MDW
1 stop6h 30m
Southwest
Wed 7/155:30 pm
MDW
-
PWM
1 stop4h 30m
Southwest
Deal found 5/28$317
This Southwest deal was found by Cheapflights users on 5/27. 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.
Wed 9/237:45 am
PWM
-
MDW
Nonstop2h 35m
Southwest
Sat 9/263:20 pm
MDW
-
PWM
Nonstop2h 15m
Southwest
Deal found 5/27$318
This Delta deal was found by Cheapflights users on 5/28. 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 7/1512:40 pm
PWM
-
MDW
1 stop6h 45m
Delta
Sat 7/184:22 pm
MDW
-
PWM
1 stop5h 52m
Delta
Deal found 5/28$322
This Delta deal was found by Cheapflights users on 5/28. 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 7/146:25 am
PWM
-
MDW
2 stops10h 50m
Delta
Sat 7/184:22 pm
MDW
-
PWM
1 stop5h 52m
Delta
Deal found 5/28$327

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 May 30, 2026.

Most accurate provider

Expedia
1 star

Most trusted provider

Expedia
3 stars

Round-trip from

$270
(Southwest)

One-way from

$99
(Southwest)

Popular in

December

Cheapest in

September

Average price

$318

Good round-trip deal

$388 or less

Good one-way deal

$197 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
Highest demand for flights based on searches. 9% potential increase in price ($35 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 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 May 30, 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

Cheapest round-trip

PortlandChicago

PWM - MDW

PWMMDW

Portland

Wed 9/16

7:45 am-9:20 am

Nonstop2h 35m

Chicago Midway

Sat 9/19

3:20 pm-6:35 pm

Nonstop2h 15m

$287

PortlandChicago

PWM - MDW

PWMMDW

Portland

Tue 9/1

11:50 am-6:01 pm

1 stop7h 11m

Chicago Midway

Wed 9/9

6:00 am-12:22 pm

1 stop5h 22m

$317

PortlandChicago

PWM - MDW

PWMMDW

Portland

Wed 7/15

5:30 am-11:00 am

1 stop6h 30m

Chicago Midway

Tue 7/21

5:30 pm-11:00 pm

1 stop4h 30m

$317

PortlandChicago

PWM - MDW

PWMMDW

Portland

Wed 7/22

6:00 am-11:56 am

1 stop6h 56m

Chicago Midway

Tue 7/28

12:41 pm-11:30 pm

2 stops9h 49m

$322

PortlandChicago

PWM - MDW

PWMMDW

Portland

Wed 7/15

6:25 am-12:38 pm

2 stops7h 13m

Chicago Midway

Sat 7/18

4:22 pm-11:14 pm

1 stop5h 52m

$327

PortlandChicago

PWM - MDW

PWMMDW

Portland

Sat 6/13

5:35 am-4:45 pm

2 stops12h 10m

Chicago Midway

Tue 6/16

8:40 am-10:55 pm

3 stops13h 15m

$328
Quickest round-trip

PortlandChicago

PWM - MDW

PWMMDW

Portland

Sat 10/24

4:40 pm-6:10 pm

Nonstop2h 30m

Chicago Midway

Tue 10/27

6:15 pm-9:30 pm

Nonstop2h 15m

$329

PortlandChicago

PWM - MDW

PWMMDW

Portland

Sat 8/22

6:10 am-3:38 pm

2 stops10h 28m

Chicago Midway

Wed 8/26

6:05 am-1:07 pm

1 stop6h 02m

$332

PortlandChicago

PWM - MDW

PWMMDW

Portland

Tue 7/14

6:25 am-4:15 pm

2 stops10h 50m

Chicago Midway

Tue 7/21

6:00 am-4:50 pm

2 stops9h 50m

$337

PortlandChicago

PWM - MDW

PWMMDW

Portland

Wed 7/15

12:40 pm-6:25 pm

1 stop6h 45m

Chicago Midway

Mon 7/20

9:19 am-4:01 pm

1 stop5h 42m

$369

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/25

Showing 1-10 of 22 resultsSorted by cheapest first
1
2
3
  • Most accurate provider: When it comes to deals on Portland, Maine-Chicago Midway Airport flights, users find the pricing of Expedia to be most consistent on Cheapflights vs. Expedia Users can find the same prices on Portland, Maine-Chicago Midway Airport flight deals on Cheapflights vs. Expedia <90% 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 Expedia the most. Expedia 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 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 May 30, 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 evening tend to be the most expensive. A flight in the afternoon could potentially save you up to 24% 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 May 30, 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
4,262 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Walter,May 2026

LAS - BUR

Short but excellent flight. Everyone was friendly and professional it was a great flight!
Southwest
8.0
Very good
4,262 reviews
Southwest
8.0
Very good
4,262 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Walter,May 2026

LAS - BUR

Short but excellent flight. Everyone was friendly and professional it was a great flight!

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 and Delta fly from Portland, Maine to Chicago Midway Airport in about 2h 35m. The time it takes to get you to your destination can typically vary by up to 4h 36m. Airlines will cover a distance of 892 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    Southwest, at $267, was found to be the cheapest airline from Portland, Maine to Chicago Midway Airport..

  • 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 $354, our data shows the cheapest flight currently is $154. When looking at the most popular route, (Portland - Chicago Midway), you can expect to pay $227 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.

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
Benton Harbor
Lansing
Merrillville
Hammond
Porter

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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
Bangor to O'Hare Intl flights
Boston to Rockford 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 May 30, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$267Average$397FlexibilityNo cancel feeOn-time63%

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