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Maine

$68+ 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 2/13. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PWM
Mar 10 — Mar 171
Tue 3/10
Tue 3/17
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 February 8, 2026.

This Southwest deal was found by Cheapflights users on 2/7. 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 3/77:40 am
MDW
-
BOS
Nonstop2h 15m
Southwest
Mon 3/96:25 pm
BOS
-
MDW
Nonstop3h 00m
Southwest
Deal found 2/7$133
This Southwest deal was found by Cheapflights users on 2/5. 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 2/176:35 pm
MDW
-
BOS
Nonstop2h 15m
Southwest
Thu 2/195:20 am
BOS
-
MDW
Nonstop2h 50m
Southwest
Deal found 2/5$135
This Southwest deal was found by Cheapflights users on 2/7. 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 2/266:05 am
MDW
-
BOS
Nonstop2h 20m
Southwest
Thu 3/511:50 am
BOS
-
MDW
Nonstop2h 50m
Southwest
Deal found 2/7$137
This Southwest deal was found by Cheapflights users on 2/7. 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 2/146:10 pm
MDW
-
BOS
Nonstop2h 15m
Southwest
Sat 3/146:40 pm
BOS
-
MDW
1 stop5h 00m
Southwest
Deal found 2/7$141
This Southwest deal was found by Cheapflights users on 2/5. 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 4/33:30 pm
MDW
-
BOS
Nonstop2h 15m
Southwest
Tue 4/710:45 am
BOS
-
MDW
Nonstop2h 40m
Southwest
Deal found 2/5$142
This Southwest deal was found by Cheapflights users on 2/5. 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 2/146:10 pm
MDW
-
BOS
Nonstop2h 15m
Southwest
Wed 2/185:30 am
BOS
-
MDW
Nonstop2h 50m
Southwest
Deal found 2/5$146
This Southwest deal was found by Cheapflights users on 2/4. 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 2/266:05 am
MDW
-
BOS
Nonstop2h 20m
Southwest
Mon 3/25:20 am
BOS
-
MDW
Nonstop2h 50m
Southwest
Deal found 2/4$147
This Southwest deal was found by Cheapflights users on 2/7. 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 3/77:40 am
MDW
-
BOS
Nonstop2h 15m
Southwest
Sat 3/146:35 pm
BOS
-
MDW
Nonstop2h 55m
Southwest
Deal found 2/7$148
This Southwest deal was found by Cheapflights users on 2/7. 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 3/16:05 am
MDW
-
BOS
Nonstop2h 20m
Southwest
Tue 3/35:50 am
BOS
-
MDW
2 stops9h 05m
Southwest
Deal found 2/7$152
This Kiwi.com deal was found by Cheapflights users on 2/5. 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.
Tue 3/37:30 am
MDW
-
BOS
2 stops15h 14m
Multiple Airlines
Wed 3/45:50 pm
BOS
-
MDW
1 stop21h 06m
Multiple Airlines
Deal found 2/5$154
This Delta deal was found by Cheapflights users on 2/5. 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 10/2010:35 am
MDW
-
PWM
1 stop6h 21m
Delta
Tue 10/2710:00 am
PWM
-
MDW
2 stops12h 45m
Delta
Deal found 2/5$254
This Southwest deal was found by Cheapflights users on 2/6. 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 6/25:00 pm
MDW
-
PWM
1 stop4h 20m
Southwest
Wed 6/107:30 am
PWM
-
MDW
Nonstop2h 35m
Southwest
Deal found 2/6$258

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 February 8, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$133
(Southwest)

One-way from

$68
(Southwest)

Popular in

April

Cheapest in

March

Average price

$311
Provider with most accurate pricing for Chicago (CHI)-Portland flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Portland flights.
Search Deals
From Chicago Midway to Maine
Search Deals
One-way flight from Chicago Midway to Maine
Search Deals
High demand for flights, 2% potential price rise
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
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 February 8, 2026.
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

Wed 4/1

8:15 am-2:35 pm

1 stop5h 20m

Boston Logan Intl

Tue 4/7

10:45 am-12:25 pm

Nonstop2h 40m

$142

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Sat 3/7

7:40 am-10:55 am

Nonstop2h 15m

Boston Logan Intl

Tue 3/10

7:15 am-9:10 am

Nonstop2h 55m

$147

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Thu 2/26

6:05 am-9:25 am

Nonstop2h 20m

Boston Logan Intl

Mon 3/2

5:20 am-7:10 am

Nonstop2h 50m

$147

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Sun 3/1

6:05 am-9:25 am

Nonstop2h 20m

Boston Logan Intl

Tue 3/3

5:50 am-1:55 pm

2 stops9h 05m

$152

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 2/18

6:00 am-1:40 pm

1 stop6h 40m

Boston Logan Intl

Sat 2/21

5:45 pm-7:35 pm

Nonstop2h 50m

$156

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 3/11

4:45 pm-10:10 pm

1 stop4h 25m

Boston Logan Intl

Tue 3/24

11:25 am-1:15 pm

Nonstop2h 50m

$157

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 2/27

6:05 am-9:25 am

Nonstop2h 20m

Boston Logan Intl

Mon 3/2

5:20 am-7:10 am

Nonstop2h 50m

$157

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Sat 4/4

7:40 am-10:55 am

Nonstop2h 15m

Boston Logan Intl

Wed 4/8

10:45 am-12:25 pm

Nonstop2h 40m

$167

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 4/3

5:40 pm-11:10 pm

1 stop4h 30m

Boston Logan Intl

Sun 4/5

7:05 am-9:00 am

Nonstop2h 55m

$187

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Sat 3/14

9:20 am-4:10 pm

1 stop5h 50m

Boston Logan Intl

Mon 3/16

6:25 pm-8:25 pm

Nonstop3h 00m

$187

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/7

Showing 1-10 of 48 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 February 8, 2026.

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 55% on your trip compared to booking a flight in the evening.

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 February 8, 2026.
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
4,280 reviews

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.5

Food

7.0

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
8.0
Very good
4,280 reviews
Southwest
8.0
Very good
4,280 reviews

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.5

Food

7.0

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 5h 20m. Your travel time can differ by up to 10m. 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 February 8, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$259Average$460FlexibilityNo cancel feeOn-time63%

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