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Maine

$64+ 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 2/2. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PWM
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
1 adult, Economy
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Cheap 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 December 12, 2025.

This Southwest deal was found by Cheapflights users on 12/10. 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.
Sat 12/1312:50 pmMDW - BOS
Nonstop2h 15mSouthwest
Sun 12/145:15 amBOS - MDW
Nonstop2h 45mSouthwest
Deal found 12/10$157
This Southwest deal was found by Cheapflights users on 12/10. 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.
Fri 12/265:30 amMDW - BOS
Nonstop2h 15mSouthwest
Thu 1/15:30 amBOS - MDW
Nonstop2h 45mSouthwest
Deal found 12/10$162
This Southwest deal was found by Cheapflights users on 12/10. 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.
Sun 12/149:35 amMDW - BOS
Nonstop2h 15mSouthwest
Sun 12/146:55 pmBOS - MDW
Nonstop2h 50mSouthwest
Deal found 12/10$187
This Southwest deal was found by Cheapflights users on 12/10. 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.
Sat 12/139:50 amMDW - BOS
Nonstop2h 20mSouthwest
Tue 12/165:45 amBOS - MDW
2 stops8h 15mSouthwest
Deal found 12/10$202
This Southwest deal was found by Cheapflights users on 12/11. 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 12/256:15 pmMDW - BOS
Nonstop2h 20mSouthwest
Wed 12/315:35 pmBOS - MDW
1 stop4h 30mSouthwest
Deal found 12/11$203
This Southwest deal was found by Cheapflights users on 12/10. 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.
Mon 12/151:30 pmMDW - BOS
Nonstop2h 15mSouthwest
Mon 12/156:00 pmBOS - MDW
1 stop5h 35mSouthwest
Deal found 12/10$217
This Southwest deal was found by Cheapflights users on 12/9. 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 12/276:00 amMDW - BOS
Nonstop2h 15mSouthwest
Fri 1/25:15 amBOS - MDW
Nonstop2h 45mSouthwest
Deal found 12/9$226
This Southwest deal was found by Cheapflights users on 12/10. 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.
Sat 12/208:40 pmMDW - BOS
Nonstop2h 15mSouthwest
Sat 1/37:05 pmBOS - MDW
1 stop5h 50mSouthwest
Deal found 12/10$227
This Southwest deal was found by Cheapflights users on 12/10. 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 12/235:25 pmMDW - PWM
2 stops5h 40mSouthwest
Sat 1/35:15 amPWM - MDW
1 stop4h 40mSouthwest
Deal found 12/10$329
This Southwest deal was found by Cheapflights users on 12/11. 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 12/125:10 amMDW - PWM
1 stop5h 00mSouthwest
Sat 1/175:10 amPWM - MDW
1 stop7h 15mSouthwest
Deal found 12/11$339
This Delta deal was found by Cheapflights users on 12/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/1710:49 amMDW - PWM
2 stops11h 32mDelta
Tue 1/66:00 amPWM - MDW
2 stops13h 32mDelta
Deal found 12/10$374
This Southwest deal was found by Cheapflights users on 12/10. 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.
Wed 12/176:40 amMDW - PWM
1 stop4h 30mSouthwest
Wed 12/173:30 pmPWM - MDW
1 stop6h 35mSouthwest
Deal found 12/10$434

Find flight deals from Midway to Maine

Keep the following information in mind while searching for Midway to Maine flight deals. Data was last updated December 12, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$127
(Southwest)

One-way from

$64
(Priceline)

Popular in

April

Cheapest in

September

Average price

$264
Provider with most accurate pricing for Chicago (CHI)-Boston Logan Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Boston Logan Intl flights.
Search Deals
From Chicago Midway to Maine
Search Deals
One-way flight from Chicago Midway to Maine
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($13 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 December 12, 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

Sat 1/17

8:40 am-4:10 pm

1 stop6h 30m

Boston Logan Intl

Sun 1/18

5:50 am-1:55 pm

2 stops9h 05m

$152

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 1/7

2:35 pm-9:45 pm

1 stop6h 10m

Boston Logan Intl

Sat 1/17

5:30 am-7:20 am

Nonstop2h 50m

$162

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Mon 2/16

6:05 am-9:25 am

Nonstop2h 20m

Boston Logan Intl

Tue 2/17

5:00 pm-9:40 pm

1 stop5h 40m

$167

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Thu 1/8

6:00 am-1:40 pm

1 stop6h 40m

Boston Logan Intl

Sun 1/11

5:20 am-7:10 am

Nonstop2h 50m

$167

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 1/7

2:00 pm-5:10 pm

Nonstop2h 10m

Boston Logan Intl

Sun 1/11

5:20 am-7:10 am

Nonstop2h 50m

$167

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 1/9

2:00 pm-5:10 pm

Nonstop2h 10m

Boston Logan Intl

Mon 1/12

5:50 am-1:55 pm

2 stops9h 05m

$172

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 2/18

1:50 pm-9:25 pm

1 stop6h 35m

Boston Logan Intl

Thu 2/19

5:20 am-7:10 am

Nonstop2h 50m

$172

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Thu 1/8

2:35 pm-9:45 pm

1 stop6h 10m

Boston Logan Intl

Tue 1/13

3:20 pm-7:00 pm

1 stop4h 40m

$182

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Tue 1/6

2:00 pm-5:10 pm

Nonstop2h 10m

Boston Logan Intl

Sun 1/11

5:20 am-7:10 am

Nonstop2h 50m

$187

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Tue 3/10

3:35 pm-11:00 pm

1 stop6h 25m

Boston Logan Intl

Thu 3/12

11:50 am-1:40 pm

Nonstop2h 50m

$187

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/11

Showing 1-10 of 52 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 December 12, 2025.

A simple way to save on the total cost of your ticket is to fly from Chicago Midway Airport to Maine in the afternoon. If you’re flexible enough to do this you can expect to save up to 72% on your trip compared to booking a flight in the morning.

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 December 12, 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
7.9
Good
4,253 reviews

Food

7.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Overall

7.9

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
7.9
Good
4,253 reviews
Southwest
7.9
Good
4,253 reviews

Food

7.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Overall

7.9

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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 6h 30m. Your travel time can differ by up to 5h 25m. Chicago Midway Airport and Maine are separated by a distance of 857 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.

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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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 December 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$313Average$411FlexibilityNo cancel feeOn-time63%

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