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Midway

$68+ 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 1/27. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MDW
Feb 20 — Feb 271
Fri 2/20
Fri 2/27
1 adult, Economy
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Cheap 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 January 21, 2026.

This Southwest deal was found by Cheapflights users on 1/20. 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 2/75:30 am
BOS
-
MDW
Nonstop2h 50m
Southwest
Sun 2/81:50 pm
MDW
-
BOS
1 stop6h 35m
Southwest
Deal found 1/20$132
This Southwest deal was found by Cheapflights users on 1/19. 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 2/65:45 pm
BOS
-
MDW
Nonstop2h 50m
Southwest
Mon 2/96:35 pm
MDW
-
BOS
Nonstop2h 15m
Southwest
Deal found 1/19$135
This Southwest deal was found by Cheapflights users on 1/20. 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.
Sun 2/85:30 am
BOS
-
MDW
Nonstop2h 50m
Southwest
Fri 2/137:40 pm
MDW
-
BOS
Nonstop2h 15m
Southwest
Deal found 1/20$137
This Southwest deal was found by Cheapflights users on 1/19. 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 2/712:55 pm
BOS
-
MDW
2 stops6h 45m
Southwest
Mon 2/96:35 pm
MDW
-
BOS
Nonstop2h 15m
Southwest
Deal found 1/19$138
This Southwest deal was found by Cheapflights users on 1/19. 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 1/225:30 am
BOS
-
MDW
Nonstop2h 50m
Southwest
Mon 1/265:35 pm
MDW
-
BOS
Nonstop2h 15m
Southwest
Deal found 1/19$141
This Southwest deal was found by Cheapflights users on 1/19. 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 1/285:30 am
BOS
-
MDW
Nonstop2h 50m
Southwest
Wed 1/282:00 pm
MDW
-
BOS
Nonstop2h 10m
Southwest
Deal found 1/19$142
This Southwest deal was found by Cheapflights users on 1/18. 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.
Sat 1/312:50 pm
BOS
-
MDW
1 stop5h 10m
Southwest
Mon 2/25:35 pm
MDW
-
BOS
Nonstop2h 15m
Southwest
Deal found 1/18$146
This Kiwi.com deal was found by Cheapflights users on 1/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/46:00 am
BOS
-
MDW
1 stop14h 07m
Frontier
Sun 3/82:41 pm
MDW
-
BOS
1 stop20h 00m
Frontier
Deal found 1/19$149
This Southwest deal was found by Cheapflights users on 1/19. 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 2/65:45 pm
BOS
-
MDW
Nonstop2h 50m
Southwest
Sun 2/81:50 pm
MDW
-
BOS
1 stop6h 35m
Southwest
Deal found 1/19$151
This Southwest deal was found by Cheapflights users on 1/18. 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.
Fri 1/235:30 am
BOS
-
MDW
Nonstop2h 50m
Southwest
Fri 1/309:50 am
MDW
-
BOS
1 stop5h 20m
Southwest
Deal found 1/18$152
This Southwest deal was found by Cheapflights users on 1/20. 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 2/289:00 am
BOS
-
MDW
2 stops8h 20m
Southwest
Sun 3/16:05 am
MDW
-
BOS
Nonstop2h 20m
Southwest
Deal found 1/20$153
This Delta deal was found by Cheapflights users on 1/19. 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.
Thu 2/2612:13 pm
PWM
-
MDW
1 stop6h 24m
Delta
Tue 3/31:29 pm
MDW
-
PWM
2 stops8h 37m
Delta
Deal found 1/19$234

Find flight deals from Maine to Midway

Keep the following information in mind while searching for Maine to Midway flight deals. Data was last updated January 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$132
(Southwest)

One-way from

$68
(Southwest)

Popular in

December

Cheapest in

September

Average price

$355
Provider with most accurate pricing for Portland-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Portland-Chicago (CHI) flights.
Search Deals
From Maine to Chicago Midway
Search Deals
One-way flight from Maine to Chicago Midway
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($41 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

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 January 21, 2026.
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

Wed 2/18

5:30 am-7:20 am

Nonstop2h 50m

Chicago Midway

Wed 2/25

5:35 pm-8:50 pm

Nonstop2h 15m

$137

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sat 2/7

5:30 am-7:20 am

Nonstop2h 50m

Chicago Midway

Sun 2/8

2:00 pm-5:10 pm

Nonstop2h 10m

$147

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 2/26

5:00 am-6:55 am

Nonstop2h 55m

Chicago Midway

Fri 3/6

7:00 pm-10:15 pm

Nonstop2h 15m

$147

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 2/5

5:20 am-7:10 am

Nonstop2h 50m

Chicago Midway

Sun 2/8

1:50 pm-9:25 pm

1 stop6h 35m

$151

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sat 2/28

5:00 am-1:30 pm

2 stops9h 30m

Chicago Midway

Sun 3/1

6:05 am-9:25 am

Nonstop2h 20m

$153

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Mon 2/2

5:30 am-7:20 am

Nonstop2h 50m

Chicago Midway

Wed 2/4

5:35 pm-8:50 pm

Nonstop2h 15m

$161

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Mon 2/23

5:20 am-7:10 am

Nonstop2h 50m

Chicago Midway

Wed 2/25

5:35 pm-8:50 pm

Nonstop2h 15m

$167

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 2/11

9:35 am-2:55 pm

1 stop6h 20m

Chicago Midway

Mon 2/16

6:05 am-9:25 am

Nonstop2h 20m

$171

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 4/29

6:20 pm-8:10 pm

Nonstop2h 50m

Chicago Midway

Sat 5/2

7:45 am-11:00 am

Nonstop2h 15m

$176

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 2/19

12:00 pm-7:35 pm

2 stops8h 35m

Chicago Midway

Thu 2/26

6:05 am-9:25 am

Nonstop2h 20m

$192

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/20

Showing 1-10 of 40 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 January 21, 2026.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 11% on flights from Maine to Chicago Midway Airport by exploring options for tickets in the morning.

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 $137, Southwest can have you in Chicago Midway Airport from Maine in 2h 50m. 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.

  • 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.

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

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.
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Philadelphia to Midway flights
Miami to O'Hare Intl flights
Denver to Midway flights
Cleveland to O'Hare Intl flights
Detroit to O'Hare Intl flights
Minneapolis to Midway flights
Reagan-National to Midway flights
Sacramento to O'Hare Intl flights
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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 January 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$246Average$397FlexibilityNo cancel feeOn-time63%
DeltaCheapest$262Average$327FlexibilityNo cancel feeOn-timeN/A

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