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Maine

$69+ Cheap flights from Midway (MDW) to Maine

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 12/3. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PWM
Oct 14 — Oct 211
Tue 10/14
Tue 10/21
1 adult, Economy
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Cheap flight deals from Midway to Maine

Keep the following information in mind while searching for Midway to Maine flight deals. Data was last updated September 14, 2025.

Round-trip from

$131
(Southwest)

One-way from

$69
(Southwest)

Popular in

December

Cheapest in

February

Average price

$323
From Chicago Midway to Maine
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One-way flight from Chicago Midway to Maine
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Highest demand for flights based on searches. 9% potential increase in price ($36 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Midway to Maine

Cheapest flights from Midway to Maine
Explore the most affordable flight options available from Midway to Maine. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 14, 2025.

This Southwest deal was found by Cheapflights users on 9/12. 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 10/209:20 pmMDW - BOS
Nonstop2h 20mSouthwest
Tue 10/215:30 amBOS - MDW
1 stop7h 30mSouthwest
Deal found 9/12$131
This Southwest deal was found by Cheapflights users on 9/12. 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 11/147:15 pmMDW - BOS
Nonstop2h 15mSouthwest
Sun 11/165:15 amBOS - MDW
Nonstop2h 45mSouthwest
Deal found 9/12$132
This Southwest deal was found by Cheapflights users on 9/13. 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 9/224:45 pmMDW - BOS
Nonstop2h 20mSouthwest
Mon 9/298:20 pmBOS - MDW
Nonstop2h 35mSouthwest
Deal found 9/13$137
This Southwest deal was found by Cheapflights users on 9/13. 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 11/141:50 pmMDW - BOS
2 stops8h 05mSouthwest
Mon 11/175:35 pmBOS - MDW
1 stop4h 30mSouthwest
Deal found 9/13$138
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 10/295:35 amMDW - BOS
1 stop4h 45mSouthwest
Thu 10/303:50 pmBOS - MDW
1 stop7h 30mSouthwest
Deal found 9/11$139
This Southwest deal was found by Cheapflights users on 9/12. 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 10/196:05 amMDW - BOS
Nonstop2h 15mSouthwest
Tue 10/215:05 pmBOS - MDW
1 stop8h 00mSouthwest
Deal found 9/12$142
This Southwest deal was found by Cheapflights users on 9/13. 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 11/276:55 amMDW - BOS
Nonstop2h 15mSouthwest
Wed 12/35:35 pmBOS - MDW
1 stop4h 30mSouthwest
Deal found 9/13$143
This CheapOair deal was found by Cheapflights users on 9/12. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/266:21 amMDW - BOS
1 stop24h 50mFrontier
Sat 10/48:56 amBOS - MDW
1 stop28h 48mFrontier
Deal found 9/12$144
This Southwest deal was found by Cheapflights users on 9/12. 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 9/203:55 pmMDW - BOS
1 stop4h 35mSouthwest
Mon 9/228:20 pmBOS - MDW
Nonstop2h 35mSouthwest
Deal found 9/12$147
This Southwest deal was found by Cheapflights users on 9/13. 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 10/225:35 amMDW - PWM
1 stop4h 40mSouthwest
Tue 10/284:00 pmPWM - MDW
Nonstop2h 35mSouthwest
Deal found 9/13$241
This Delta deal was found by Cheapflights users on 9/13. 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 11/126:00 amMDW - PWM
1 stop5h 30mDelta
Sat 11/1512:48 pmPWM - MDW
1 stop6h 20mDelta
Deal found 9/13$251
This Delta deal was found by Cheapflights users on 9/12. 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.
Sat 9/271:08 pmMDW - PWM
1 stop3h 36mDelta
Wed 10/16:00 amPWM - MDW
1 stop6h 48mDelta
Deal found 9/12$258

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Maine 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 14, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Maine that are best for you.

Fly from

Midway

Fly to

Maine

Route

Depart

Return

Price

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 11/14

9:05 pm-8:05 am

1 stop10h 00m

Boston Logan Intl

Sun 11/16

5:15 am-7:00 am

Nonstop2h 45m

$133

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 10/29

5:35 am-11:20 am

1 stop4h 45m

Boston Logan Intl

Thu 10/30

3:50 pm-10:20 pm

1 stop7h 30m

$139

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 11/14

1:50 pm-10:55 pm

2 stops8h 05m

Boston Logan Intl

Sat 11/15

7:45 am-12:25 pm

1 stop5h 40m

$142

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 10/29

1:15 pm-9:10 pm

2 stops6h 55m

Boston Logan Intl

Tue 11/4

5:35 pm-9:05 pm

1 stop4h 30m

$144

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Sat 9/20

3:55 pm-9:30 pm

1 stop4h 35m

Boston Logan Intl

Mon 9/22

8:20 pm-9:55 pm

Nonstop2h 35m

$147

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Thu 11/27

6:55 am-10:10 am

Nonstop2h 15m

Boston Logan Intl

Wed 12/3

9:05 am-6:25 pm

2 stops10h 20m

$152

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 11/26

9:40 pm-8:10 am

1 stop9h 30m

Boston Logan Intl

Fri 11/28

6:50 am-3:40 pm

1 stop9h 50m

$168

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 10/24

5:20 pm-11:55 pm

1 stop5h 35m

Boston Logan Intl

Sat 10/25

6:30 am-4:25 pm

2 stops10h 55m

$191

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Mon 10/20

5:50 am-12:20 pm

1 stop5h 30m

Boston Logan Intl

Thu 10/23

3:50 pm-8:35 pm

1 stop5h 45m

$197

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Thu 11/6

2:25 pm-5:40 pm

Nonstop2h 15m

Boston Logan Intl

Mon 11/10

6:55 pm-8:45 pm

Nonstop2h 50m

$197

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/13

Showing 1-10 of 53 results
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Best time to book a flight from Midway to Maine

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

Cheapflights Insights

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

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

Find hourly flight availability from Midway to Maine. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 14, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago Midway Airport to Maine as you normally would.

Reviews of airlines servicing Maine

Get insights into the airlines that provide service to Maine. 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 Maine. Reviews last updated September 14, 2025.
Read reviews from past customers who have flown Southwest from Chicago Midway Airport to Maine. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,247 reviews

Overall

8.0

Food

7.0

Entertainment

7.5

Crew

8.6

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,247 reviews
Southwest
8.0
Very good
4,247 reviews

Overall

8.0

Food

7.0

Entertainment

7.5

Crew

8.6

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

Find useful and relevant information for your journey from Midway to Maine. 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 Chicago Midway Airport to Maine?

    Southwest and Delta can get you from Chicago Midway Airport to Maine in just under 5h 30m. Your travel time can differ by up to 4h 30m. Chicago Midway Airport and Maine are separated by a distance of 892 mi. This flight may include one or multiple stops.

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

    When deciding which route to take from Chicago Midway Airport to Maine consider Chicago Midway - Boston Logan Intl, Chicago Midway - Portland or Chicago Midway - Bangor as they are the most popular.

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

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

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

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

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

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

    Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Maine (average of $296). Flying from Chicago Midway Airport to Maine in July is currently the most expensive (average of $394). 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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Alternative routes for Midway to Maine

See prices for flight routes from nearby airports that may be better suited for you.
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Midway to Hobby flights
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Midway to San Francisco flights
Midway to Miami flights
O'Hare Intl to Hobby flights
O'Hare Intl to Raleigh flights
O'Hare Intl to Minneapolis flights
O'Hare Intl to Palm Springs flights
O'Hare Intl to Love Field flights
Midway to Seattle flights

Top airline flying from Midway to Maine

Discover the top airline that operate flights from Midway to Maine. 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 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$276Average$411FlexibilityNo cancel feeOn-time63%

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