HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Midway

$62+ 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 1/7. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MDW
Jan 2 — Jan 91
Fri 1/2
Fri 1/9
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Maine to Midway 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.

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 December 3, 2025.

This Southwest deal was found by Cheapflights users on 12/1. 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 12/95:30 amBOS - MDW
Nonstop2h 45mSouthwest
Thu 12/111:30 pmMDW - BOS
Nonstop2h 15mSouthwest
Deal found 12/1$127
This Southwest deal was found by Cheapflights users on 12/2. 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 12/95:30 amBOS - MDW
Nonstop2h 45mSouthwest
Thu 12/189:35 amMDW - BOS
Nonstop2h 15mSouthwest
Deal found 12/2$137
This Southwest deal was found by Cheapflights users on 12/1. 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 12/315:35 pmBOS - MDW
1 stop4h 30mSouthwest
Wed 1/75:35 pmMDW - BOS
Nonstop2h 15mSouthwest
Deal found 12/1$146
This Kiwi.com deal was found by Cheapflights users on 12/2. 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 12/1812:22 pmBOS - MDW
1 stop10h 36mFrontier
Wed 12/248:15 amMDW - BOS
1 stop15h 59mFrontier
Deal found 12/2$148
This Southwest deal was found by Cheapflights users on 12/1. 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 12/145:15 amBOS - MDW
Nonstop2h 45mSouthwest
Sun 1/256:35 pmMDW - BOS
Nonstop2h 15mSouthwest
Deal found 12/1$162
This Southwest deal was found by Cheapflights users on 12/1. 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 12/315:35 pmBOS - MDW
1 stop4h 30mSouthwest
Mon 1/57:15 pmMDW - BOS
Nonstop2h 15mSouthwest
Deal found 12/1$170
This Southwest deal was found by Cheapflights users on 12/2. 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 12/95:30 amBOS - MDW
Nonstop2h 45mSouthwest
Wed 12/101:30 pmMDW - BOS
Nonstop2h 15mSouthwest
Deal found 12/2$172
This Kiwi.com deal was found by Cheapflights users on 12/1. 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 12/910:56 amBOS - MDW
2 stops22h 50mMultiple Airlines
Tue 1/66:52 amMDW - BOS
1 stop17h 27mMultiple Airlines
Deal found 12/1$181
This Delta deal was found by Cheapflights users on 12/2. 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 12/1611:55 amBGR - MDW
2 stops7h 05mDelta
Mon 1/191:26 pmMDW - BGR
2 stops8h 59mDelta
Deal found 12/2$284
This Kiwi.com deal was found by Cheapflights users on 12/1. 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.
Mon 12/89:46 amPWM - MDW
1 stop13h 12mMultiple Airlines
Thu 12/116:15 amMDW - PWM
2 stops25h 51mMultiple Airlines
Deal found 12/1$316
This Southwest deal was found by Cheapflights users on 12/1. 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 12/125:25 pmPWM - MDW
1 stop6h 35mSouthwest
Mon 12/156:40 amMDW - PWM
1 stop7h 15mSouthwest
Deal found 12/1$324
This Kiwi.com deal was found by Cheapflights users on 12/1. 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.
Fri 12/1211:21 amPWM - MDW
2 stops12h 18mMultiple Airlines
Sun 12/146:37 pmMDW - PWM
1 stop13h 29mMultiple Airlines
Deal found 12/1$325

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 December 3, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$117
(Southwest)

One-way from

$62
(Southwest)

Popular in

December

Cheapest in

September

Average price

$458
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. 11% potential increase in price ($46 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($9 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 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 December 3, 2025.
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

Tue 1/20

5:30 am-7:20 am

Nonstop2h 50m

Chicago Midway

Sat 1/24

2:40 pm-8:30 pm

1 stop4h 50m

$128

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 1/21

5:29 am-8:52 am

1 stop4h 23m

Chicago Midway

Mon 1/26

6:35 pm-11:51 pm

1 stop4h 16m

$137

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 1/8

2:40 pm-4:30 pm

Nonstop2h 50m

Chicago Midway

Mon 1/12

5:35 pm-8:50 pm

Nonstop2h 15m

$137

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 1/9

5:30 am-7:20 am

Nonstop2h 50m

Chicago Midway

Mon 1/12

6:50 am-2:20 pm

1 stop6h 30m

$144

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Mon 2/23

5:00 pm-9:40 pm

1 stop5h 40m

Chicago Midway

Fri 2/27

7:40 pm-10:55 pm

Nonstop2h 15m

$144

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 1/23

5:30 am-7:20 am

Nonstop2h 50m

Chicago Midway

Mon 1/26

9:50 am-4:10 pm

1 stop5h 20m

$144

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 1/22

5:30 am-7:20 am

Nonstop2h 50m

Chicago Midway

Sun 1/25

6:35 pm-9:50 pm

Nonstop2h 15m

$154

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sat 1/24

12:55 pm-6:40 pm

2 stops6h 45m

Chicago Midway

Tue 1/27

1:50 pm-9:25 pm

1 stop6h 35m

$157

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sun 2/22

5:00 am-6:55 am

Nonstop2h 55m

Chicago Midway

Thu 2/26

4:55 pm-11:40 pm

1 stop5h 45m

$159

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 1/29

5:30 am-7:20 am

Nonstop2h 50m

Chicago Midway

Sun 2/1

2:40 pm-10:10 pm

1 stop6h 30m

$164

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/1

Showing 1-10 of 52 results
1
2
3
...
6

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 December 3, 2025.

Unlike in the evening, when flights are generally more expensive, you can save up to 31% 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 $128, 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

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

Alternative routes for Maine to Midway

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to O'Hare Intl flights
Dallas/Fort Worth to O'Hare Intl flights
Newark to O'Hare Intl flights
LaGuardia to O'Hare Intl flights
Los Angeles to O'Hare Intl flights
Seattle to O'Hare Intl flights
Baltimore to O'Hare Intl flights
San Francisco to O'Hare Intl flights
Dulles Intl to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
Denver to O'Hare Intl flights
Atlanta to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
Philadelphia to O'Hare Intl flights
John F Kennedy Intl to Midway flights
Sky Harbor Intl to O'Hare Intl flights
LaGuardia to Midway flights
Tampa to O'Hare Intl flights
Boston to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
Ontario to O'Hare Intl flights
Love Field to O'Hare Intl flights
Minneapolis to O'Hare Intl flights
Atlanta to Midway flights
Dulles Intl to Midway flights
San Diego to O'Hare Intl flights
Charlotte to O'Hare Intl flights
Austin to O'Hare Intl flights
San Francisco to Midway flights
Santa Ana to O'Hare Intl flights
Cleveland to O'Hare Intl flights
Los Angeles to Midway flights
Portland to O'Hare Intl flights
Denver to Midway flights
Orlando to Midway flights
Reagan-National to Midway flights
Seattle to Midway flights
Orlando to O'Hare Intl flights
Raleigh to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
Hobby to O'Hare Intl flights
Minneapolis to Midway flights
Hobby to Midway flights
Philadelphia to Midway flights
Miami to O'Hare Intl flights
Baltimore to Midway flights
Salt Lake City to O'Hare Intl flights
Tampa to Midway flights
Boston to Midway flights
Detroit to O'Hare Intl flights

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 December 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$246Average$397FlexibilityNo cancel feeOn-time63%
DeltaCheapest$253Average$327FlexibilityNo cancel feeOn-timeN/A

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.