HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Maine

$59+ 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
Dec 1 — Dec 81
Mon 12/1
Mon 12/8
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Midway to Maine with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 November 1, 2025.

This Mytrip deal was found by Cheapflights users on 10/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1310:12 amMDW - BOS
1 stop21h 16mFrontier
Sat 11/1511:43 amBOS - MDW
1 stop10h 52mFrontier
Deal found 10/30$119
This Southwest deal was found by Cheapflights users on 10/30. 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 11/271:40 pmMDW - BOS
Nonstop2h 15mSouthwest
Thu 12/45:30 amBOS - MDW
Nonstop2h 45mSouthwest
Deal found 10/30$122
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Thu 12/47:23 pmMDW - BOS
1 stop13h 59mFrontier
Sun 12/711:28 amBOS - MDW
1 stop23h 24mFrontier
Deal found 10/29$123
This Southwest deal was found by Cheapflights users on 10/30. 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 12/46:15 pmMDW - BOS
Nonstop2h 20mSouthwest
Sun 12/76:50 pmBOS - MDW
1 stop5h 40mSouthwest
Deal found 10/30$127
This Southwest deal was found by Cheapflights users on 10/31. 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 11/242:25 pmMDW - BOS
Nonstop2h 15mSouthwest
Tue 12/305:15 amBOS - MDW
Nonstop2h 45mSouthwest
Deal found 10/31$129
This Southwest deal was found by Cheapflights users on 10/30. 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 12/241:30 pmMDW - BOS
Nonstop2h 15mSouthwest
Fri 1/25:15 amBOS - MDW
Nonstop2h 45mSouthwest
Deal found 10/30$131
This Southwest deal was found by Cheapflights users on 10/30. 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 11/269:35 amMDW - BOS
Nonstop2h 15mSouthwest
Wed 12/36:45 amBOS - MDW
1 stop10h 10mSouthwest
Deal found 10/30$132
This Kiwi.com deal was found by Cheapflights users on 10/30. 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.
Thu 11/276:05 amMDW - BOS
1 stop17h 39mFrontier
Thu 12/411:28 amBOS - MDW
1 stop7h 40mFrontier
Deal found 10/30$134
This Delta deal was found by Cheapflights users on 10/28. 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
Tue 11/186:00 amPWM - MDW
1 stop6h 52mDelta
Deal found 10/28$249
This Delta deal was found by Cheapflights users on 10/28. 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 11/1112:47 pmMDW - PWM
2 stops10h 07mDelta
Tue 11/186:00 amPWM - MDW
1 stop6h 52mDelta
Deal found 10/28$254
This Delta deal was found by Cheapflights users on 10/28. 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.
Fri 11/141:15 pmMDW - PWM
2 stops9h 39mDelta
Tue 11/1811:25 amPWM - MDW
2 stops7h 43mDelta
Deal found 10/28$259
This Delta deal was found by Cheapflights users on 10/29. 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 10/29$269

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 November 1, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$119
(Mytrip)

One-way from

$59
(Southwest)

Popular in

November

Cheapest in

March

Average price

$473
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
Highest demand for flights based on searches. 14% potential increase in price ($64 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 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 November 1, 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

Wed 12/24

1:30 pm-4:45 pm

Nonstop2h 15m

Boston Logan Intl

Fri 1/2

5:15 am-7:00 am

Nonstop2h 45m

$131

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 11/26

4:05 pm-7:20 pm

Nonstop2h 15m

Boston Logan Intl

Tue 12/2

10:20 am-3:20 pm

1 stop6h 00m

$132

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Mon 11/10

2:55 pm-11:15 pm

1 stop7h 20m

Boston Logan Intl

Thu 11/13

5:15 am-7:00 am

Nonstop2h 45m

$137

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Thu 11/13

9:35 am-12:50 pm

Nonstop2h 15m

Boston Logan Intl

Wed 11/19

1:35 pm-3:20 pm

Nonstop2h 45m

$147

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Mon 11/10

2:55 pm-11:15 pm

1 stop7h 20m

Boston Logan Intl

Fri 11/14

12:05 pm-8:15 pm

1 stop9h 10m

$147

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Tue 11/18

6:15 pm-9:35 pm

Nonstop2h 20m

Boston Logan Intl

Thu 11/20

5:30 am-7:15 am

Nonstop2h 45m

$147

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 11/14

7:15 pm-10:30 pm

Nonstop2h 15m

Boston Logan Intl

Sun 11/16

5:15 am-7:00 am

Nonstop2h 45m

$147

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Sat 11/22

5:35 pm-1:00 am

1 stop6h 25m

Boston Logan Intl

Fri 11/28

6:50 am-3:40 pm

1 stop9h 50m

$152

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Thu 11/13

9:34 am-4:07 pm

1 stop5h 33m

Portland

Tue 11/18

6:00 am-11:52 am

1 stop6h 52m

$249

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Tue 11/11

12:47 pm-11:54 pm

2 stops10h 07m

Portland

Tue 11/18

6:00 am-11:52 am

1 stop6h 52m

$254

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/30

Showing 1-10 of 48 results
1
2
3
...
5

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 November 1, 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 November 1, 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
4,245 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Comfort

8.0

Boarding

8.1

Overall

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
4,245 reviews
Southwest
8.0
Very good
4,245 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Comfort

8.0

Boarding

8.1

Overall

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 2h 15m. Your travel time can differ by up to 3h 18m. 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Midway to Maine

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to John F Kennedy Intl flights
O'Hare Intl to Dallas/Fort Worth flights
O'Hare Intl to LaGuardia flights
O'Hare Intl to Las Vegas flights
O'Hare Intl to Sky Harbor Intl flights
O'Hare Intl to Newark flights
O'Hare Intl to Orlando flights
O'Hare Intl to Miami flights
O'Hare Intl to Denver flights
O'Hare Intl to Fort Lauderdale flights
O'Hare Intl to Los Angeles flights
O'Hare Intl to Tampa flights
O'Hare Intl to Atlanta flights
Midway to Dallas/Fort Worth flights
O'Hare Intl to San Francisco flights
O'Hare Intl to Boston flights
O'Hare Intl to Reagan-National flights
Midway to John F Kennedy Intl flights
O'Hare Intl to Fort Myers flights
Midway to LaGuardia flights
O'Hare Intl to Ontario flights
O'Hare Intl to Santa Ana flights
O'Hare Intl to New Orleans flights
O'Hare Intl to Seattle flights
O'Hare Intl to Baltimore flights
O'Hare Intl to Dulles Intl flights
Midway to Atlanta flights
Midway to Las Vegas flights
Midway to Orlando flights
O'Hare Intl to Honolulu flights
O'Hare Intl to Philadelphia flights
Midway to Sky Harbor Intl flights
O'Hare Intl to San Diego flights
Midway to Los Angeles flights
O'Hare Intl to George Bush Intcntl flights
O'Hare Intl to Nashville flights
O'Hare Intl to West Palm Beach flights
O'Hare Intl to Hobby flights
O'Hare Intl to Salt Lake City flights
O'Hare Intl to Austin flights
O'Hare Intl to Sarasota flights
Midway to Denver flights
Midway to Tampa flights
Midway to Fort Lauderdale flights
Midway to Newark flights
O'Hare Intl to Minneapolis flights
Midway to Miami flights
Midway to Baltimore flights
Midway to Hobby flights
O'Hare Intl to Charlotte 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 November 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$313Average$411FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.