HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Midway

$69+ 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 7/31. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MDW
Jul 6 — Jul 131
Sun 7/6
Sun 7/13
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

Keep the following information in mind while searching for Maine to Midway flight deals. Data was last updated July 1, 2025.

Round-trip from

$137
(Southwest)

One-way from

$69
(Southwest)

Popular in

November

Cheapest in

September

Average price

$328

Good round-trip deal

$362 or less

Good one-way deal

$169 or less
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 ($47 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2025
Search Deals
Price to beat on a round-trip flight from Maine to Chicago Midway.
Search Deals
Price to beat on a one-way flight from Maine to Chicago Midway.
Search Deals

Find 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 July 1, 2025.

This Southwest deal was found by Cheapflights users on 7/1. 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 7/85:25 amBOS - MDW
Nonstop2h 35mSouthwest
Wed 7/97:30 pmMDW - BOS
Nonstop2h 15mSouthwest
Deal found 7/1$137
This Mytrip deal was found by Cheapflights users on 6/30. 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.
Fri 8/811:55 amBOS - MDW
1 stop26h 55mFrontier
Fri 8/158:35 amMDW - BOS
1 stop23h 00mFrontier
Deal found 6/30$229
This Southwest deal was found by Cheapflights users on 6/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/305:50 pmPWM - MDW
1 stop6h 35mSouthwest
Tue 8/511:40 amMDW - PWM
Nonstop2h 15mSouthwest
Deal found 6/28$241
This Delta deal was found by Cheapflights users on 6/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/231:34 pmPWM - MDW
1 stop8h 38mDelta
Sun 8/316:00 amMDW - PWM
1 stop5h 29mDelta
Deal found 6/30$244
This Delta deal was found by Cheapflights users on 7/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/275:11 amBGR - MDW
2 stops8h 17mDelta
Tue 9/26:00 amMDW - BGR
2 stops9h 19mDelta
Deal found 7/1$374

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 July 1, 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 7/8

5:25 am-7:00 am

Nonstop2h 35m

Chicago Midway

Wed 7/9

7:30 pm-10:45 pm

Nonstop2h 15m

$137

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 8/8

11:55 am-1:50 pm

1 stop26h 55m

Chicago Midway

Fri 8/15

8:35 am-8:35 am

1 stop23h 00m

$229

PortlandChicago

PWM - MDW

PWMMDW

Portland

Wed 7/30

5:50 pm-11:25 pm

1 stop6h 35m

Chicago Midway

Tue 8/5

11:40 am-2:55 pm

Nonstop2h 15m

$241

PortlandChicago

PWM - MDW

PWMMDW

Portland

Sat 8/23

1:34 pm-9:12 pm

1 stop8h 38m

Chicago Midway

Sun 8/31

6:00 am-12:29 pm

1 stop5h 29m

$244

BangorChicago

BGR - MDW

BGRMDW

Bangor

Wed 8/27

5:11 am-12:28 pm

2 stops8h 17m

Chicago Midway

Tue 9/2

6:00 am-4:19 pm

2 stops9h 19m

$374

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 7/31

5:15 am-6:50 am

Nonstop2h 35m

$69

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sat 7/26

9:40 am-8:22 pm

1 stop11h 42m

$81

PortlandChicago

PWM - MDW

PWMMDW

Portland

Fri 10/31

10:00 am-9:44 pm

2 stops12h 44m

$124

PortlandChicago

PWM - MDW

PWMMDW

Portland

Thu 9/11

10:35 am-12:05 pm

Nonstop2h 30m

$130

PortlandChicago

PWM - MDW

PWMMDW

Portland

Sat 9/13

12:57 pm-8:53 am

1 stop20h 56m

$136

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/30

Showing 1-10 of 14 results
1
2

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 July 1, 2025.

When flying from Maine to Chicago Midway Airport, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated July 1, 2025.
Read reviews from past customers who have flown Southwest, Delta, and Allegiant Air from Maine to Chicago Midway Airport. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,275 reviews

Crew

8.6

Food

7.0

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,275 reviews
Southwest
8.0
Very good
4,275 reviews

Crew

8.6

Food

7.0

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,974 reviews
Southwest
8.0
Very good
4,275 reviews

Crew

8.6

Food

7.0

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Allegiant Air
7.2
Good
710 reviews
Southwest
8.0
Very good
4,275 reviews

Crew

8.6

Food

7.0

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Frontier
5.9
Fair
3,289 reviews
Southwest
8.0
Very good
4,275 reviews

Crew

8.6

Food

7.0

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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.

  • What are the cheapest airlines to fly from Maine to Chicago Midway Airport one-way?

    One-way options have recently been found by users for as low as $69 on Southwest. Other airlines that offer cheap prices include Frontier from $81 and Allegiant Air from $112 one-way.

  • 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.

  • What are the cheapest flights from Maine to Chicago Midway Airport?

    While on average a flight from Maine to Chicago Midway Airport is generally $327, our data shows the cheapest flight currently is $129. When looking at the most popular route, (Boston Logan Intl - Chicago Midway), you can expect to pay $123 for that flight.

  • 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.

  • What is the cheapest month to book a flight from Maine to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Maine to Chicago Midway Airport (average of $160). Flying from Maine to Chicago Midway Airport in November is currently the most expensive (average of $249). 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

Traveling to a place near Maine?

Book flights to Maine if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

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.
Dallas/Fort Worth to O'Hare Intl flights
John F Kennedy Intl to O'Hare Intl flights
Newark to O'Hare Intl flights
LaGuardia to O'Hare Intl flights
Los Angeles to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
Seattle to O'Hare Intl flights
San Francisco to O'Hare Intl flights
Boston to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
Philadelphia to O'Hare Intl flights
Baltimore to O'Hare Intl flights
Dulles Intl to O'Hare Intl flights
Raleigh to O'Hare Intl flights
Hobby to O'Hare Intl flights
Newark to Midway flights
Sky Harbor Intl to O'Hare Intl flights
Atlanta to Midway flights
John F Kennedy Intl to Midway flights
Denver to O'Hare Intl flights
Ontario to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
Santa Ana to O'Hare Intl flights
Austin to O'Hare Intl flights
San Francisco to Midway flights
Atlanta to O'Hare Intl flights
Dulles Intl to Midway flights
LaGuardia to Midway flights
Tampa to O'Hare Intl flights
Baltimore to Midway flights
San Diego to O'Hare Intl flights
Portland to O'Hare Intl flights
Orlando to O'Hare Intl flights
Charlotte to O'Hare Intl flights
Burbank to O'Hare Intl flights
Miami to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
Denver to Midway flights
Minneapolis to O'Hare Intl flights
Love Field to O'Hare Intl flights
Reagan-National to Midway flights
Minneapolis to Midway flights
Hobby to Midway flights
Philadelphia to Midway flights
Los Angeles to Midway flights
Raleigh to Midway flights
Oakland to O'Hare Intl flights
Sky Harbor Intl to Midway flights
Cleveland to O'Hare Intl flights
San Jose 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 July 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$201Average$327FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$264Average$379FlexibilityNo 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.