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Midway

$67+ Cheap flights from Maine 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 10/22. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MDW
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap flight deals from Maine to Midway

Keep the following information in mind while searching for Maine to Midway flight deals. Data was last updated September 11, 2025.

Round-trip from

$125
(Southwest)

One-way from

$67
(Southwest)

Popular in

December

Cheapest in

September

Average price

$282

Good round-trip deal

$341 or less

Good one-way deal

$203 or less
From Maine to Chicago Midway
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One-way flight from Maine to Chicago Midway
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Highest demand for flights based on searches. 12% potential increase in price ($51 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Maine to Chicago Midway.
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Price to beat on a one-way flight from Maine to Chicago Midway.
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Find flight deals from Maine to Midway

Cheapest flights from Maine to Midway
Explore the most affordable flight options available from Maine to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 11, 2025.

This Southwest deal was found by Cheapflights users on 9/11. 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 10/256:30 amBOS - MDW
2 stops10h 55mSouthwest
Mon 10/2711:25 amMDW - BOS
1 stop6h 50mSouthwest
Deal found 9/11$125
This Southwest deal was found by Cheapflights users on 9/11. 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 10/315:00 amBOS - MDW
Nonstop2h 40mSouthwest
Mon 11/36:40 amMDW - BOS
1 stop8h 55mSouthwest
Deal found 9/11$126
This Southwest deal was found by Cheapflights users on 9/10. 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 11/45:35 pmBOS - MDW
1 stop4h 30mSouthwest
Wed 11/58:25 amMDW - BOS
2 stops7h 10mSouthwest
Deal found 9/10$129
This Southwest deal was found by Cheapflights users on 9/9. 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 10/256:30 amBOS - MDW
2 stops10h 55mSouthwest
Mon 11/36:40 amMDW - BOS
1 stop8h 55mSouthwest
Deal found 9/9$130
This Southwest deal was found by Cheapflights users on 9/11. 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.
Thu 10/305:15 amBOS - MDW
Nonstop2h 40mSouthwest
Sun 11/25:45 amMDW - BOS
1 stop10h 25mSouthwest
Deal found 9/11$131
This Southwest deal was found by Cheapflights users on 9/11. 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 10/249:35 pmBOS - MDW
Nonstop2h 40mSouthwest
Sun 10/266:05 amMDW - BOS
Nonstop2h 15mSouthwest
Deal found 9/11$132
This Southwest deal was found by Cheapflights users on 9/11. 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 10/295:30 amBOS - MDW
1 stop7h 30mSouthwest
Wed 11/122:10 pmMDW - BOS
2 stops7h 05mSouthwest
Deal found 9/11$134
This Southwest deal was found by Cheapflights users on 9/11. 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 10/215:30 amBOS - MDW
1 stop7h 30mSouthwest
Wed 10/2212:30 pmMDW - BOS
1 stop7h 40mSouthwest
Deal found 9/11$136
This Delta deal was found by Cheapflights users on 9/9. 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 10/155:34 amBOS - MDW
1 stop4h 06mDelta
Sat 10/181:11 pmMDW - BOS
1 stop3h 41mDelta
Deal found 9/9$137
This Southwest deal was found by Cheapflights users on 9/11. 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 10/315:00 amBOS - MDW
Nonstop2h 40mSouthwest
Wed 11/52:10 pmMDW - BOS
2 stops7h 05mSouthwest
Deal found 9/11$140
This Southwest deal was found by Cheapflights users on 9/10. 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.
Thu 10/169:35 pmBOS - MDW
Nonstop2h 40mSouthwest
Mon 10/206:05 amMDW - BOS
Nonstop2h 15mSouthwest
Deal found 9/10$141
This Southwest deal was found by Cheapflights users on 9/11. 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 11/175:35 pmBOS - MDW
1 stop4h 30mSouthwest
Fri 11/216:45 amMDW - BOS
1 stop10h 25mSouthwest
Deal found 9/11$142

Cheapflights Fare Finder

 
Customize your flight search to find flights from Maine 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 September 11, 2025.
Use the filters below to find and compare flights from Maine to Chicago Midway Airport that are best for you.

Fly from

Maine

Fly to

Midway

Route

Depart

Return

Price

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 10/31

5:00 am-6:40 am

Nonstop2h 40m

Chicago Midway

Mon 11/3

6:40 am-4:35 pm

1 stop8h 55m

$126

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 11/13

5:29 am-8:52 am

1 stop4h 23m

Chicago Midway

Mon 11/17

6:48 pm-11:55 pm

1 stop4h 07m

$137

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Mon 11/10

1:45 pm-3:30 pm

Nonstop2h 45m

Chicago Midway

Fri 11/14

7:15 pm-10:30 pm

Nonstop2h 15m

$137

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 10/15

5:34 am-8:40 am

1 stop4h 06m

Chicago Midway

Tue 10/21

1:08 pm-8:01 pm

1 stop5h 53m

$137

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 10/15

5:15 am-6:55 am

Nonstop2h 40m

Chicago Midway

Sat 10/18

12:45 pm-4:00 pm

Nonstop2h 15m

$137

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sat 11/1

5:45 am-1:08 pm

1 stop8h 23m

Chicago Midway

Sat 11/8

1:06 pm-5:52 pm

1 stop3h 46m

$137

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 10/15

7:50 am-2:25 pm

1 stop7h 35m

Chicago Midway

Fri 10/17

9:20 pm-12:40 am

Nonstop2h 20m

$145

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 11/20

12:20 pm-7:10 pm

2 stops7h 50m

Chicago Midway

Sun 11/23

6:45 am-6:10 pm

1 stop10h 25m

$152

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Tue 9/30

5:20 am-3:00 pm

2 stops10h 40m

Chicago Midway

Wed 10/8

6:05 am-9:20 am

Nonstop2h 15m

$160

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Mon 11/17

5:45 am-1:00 pm

2 stops8h 15m

Chicago Midway

Fri 11/21

6:45 am-6:10 pm

1 stop10h 25m

$168

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/11

Showing 1-10 of 59 results
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Best time to book a flight from Maine to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Maine 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 Maine to Chicago Midway Airport

What is the cheapest time of day to fly from ME to MDW?

Find hourly flight availability from Maine 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 September 11, 2025.

When flying from Maine to Chicago Midway Airport, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Related info for your journey

Find useful and relevant information for your journey from Maine to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

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

    For as low as $126, Southwest can have you in Chicago Midway Airport from Maine in 2h 40m. The distance between Maine and Chicago Midway Airport is about 857 mi. This flight may include one or multiple stops.

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

    Most travelers choose Boston Logan Intl - Chicago Midway, Portland - Chicago Midway or Bangor - Chicago Midway when deciding on the best route from Maine to Chicago Midway Airport.

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

    While on average a flight from Maine to Chicago Midway Airport is generally $354, our data shows the cheapest flight currently is $129. When looking at the most popular route, (Boston Logan Intl - Chicago Midway), you can expect to pay $84 for that flight.

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

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

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

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

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

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

    Currently, April is the cheapest month in which you can book a flight from Maine to Chicago Midway Airport (average of $160). Flying from Maine to Chicago Midway Airport in November is currently the most expensive (average of $249). 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
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Maine to Midway

See prices for flight routes from nearby airports that may be better suited for you.
Newark to O'Hare Intl flights
LaGuardia to O'Hare Intl flights
Dallas/Fort Worth to O'Hare Intl flights
John F Kennedy Intl to O'Hare Intl flights
Los Angeles to O'Hare Intl flights
San Francisco to O'Hare Intl flights
Boston to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
Dulles Intl to O'Hare Intl flights
Baltimore to O'Hare Intl flights
Atlanta to O'Hare Intl flights
Seattle to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
John F Kennedy Intl to Midway flights
Philadelphia to O'Hare Intl flights
Ontario to O'Hare Intl flights
Newark to Midway flights
LaGuardia to Midway flights
Atlanta to Midway flights
Denver to O'Hare Intl flights
Santa Ana to O'Hare Intl flights
Baltimore to Midway flights
Dulles Intl to Midway flights
Hobby to O'Hare Intl flights
Austin to O'Hare Intl flights
Sky Harbor Intl to O'Hare Intl flights
Los Angeles to Midway flights
Orlando to O'Hare Intl flights
San Francisco to Midway flights
Minneapolis to O'Hare Intl flights
Burbank to O'Hare Intl flights
Hobby to Midway flights
George Bush Intcntl to O'Hare Intl flights
Raleigh to O'Hare Intl flights
Charlotte to O'Hare Intl flights
Minneapolis to Midway flights
Portland to O'Hare Intl flights
San Diego to O'Hare Intl flights
Denver to Midway flights
Fort Lauderdale to O'Hare Intl flights
Philadelphia to Midway flights
Cleveland to O'Hare Intl flights
Tampa to O'Hare Intl flights
San Jose to O'Hare Intl flights
Reagan-National to Midway flights
Miami to O'Hare Intl flights
Hartford to O'Hare Intl flights
Seattle to Midway flights
Kansas City to O'Hare Intl flights
Salt Lake City to O'Hare Intl flights

Top 2 airlines flying from Maine to Midway

Discover the top 2 airlines that operate flights from Maine 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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$253Average$327FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$264Average$397FlexibilityNo cancel feeOn-time63%

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