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Maine

$76+ 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 6/4. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PWM
Apr 6 — Apr 131
Sun 4/6
Sun 4/13
1 adult, Economy
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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 April 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$116
(Southwest)

One-way from

$76
(Southwest)

Popular in

December

Cheapest in

February

Average price

$425

Good round-trip deal

$375 or less

Good one-way deal

$174 or less
Provider with most accurate pricing for Chicago (CHI)-Portland flight deals.
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From Chicago Midway to Maine
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One-way flight from Chicago Midway to Maine
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Highest demand for flights based on searches. 10% potential increase in price ($40 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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Price to beat on a round-trip flight from Chicago Midway to Maine.
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Price to beat on a one-way flight from Chicago Midway to Maine.
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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 April 1, 2025.

This Southwest deal was found by Cheapflights users on 3/31. 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.
Wed 4/306:50 amMDW - BOS
1 stop6h 10mSouthwest
Wed 5/73:00 pmBOS - MDW
1 stop5h 50mSouthwest
Deal found 3/31$116
This Frontier deal was found by Cheapflights users on 4/1. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/81:19 pmMDW - BOS
1 stop10h 46mFrontier
Mon 5/1212:58 pmBOS - MDW
1 stop11h 49mFrontier
Deal found 4/1$198
This Southwest deal was found by Cheapflights users on 3/31. 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 6/305:05 amMDW - PWM
1 stop4h 35mSouthwest
Thu 7/31:20 pmPWM - MDW
1 stop5h 05mSouthwest
Deal found 3/31$229
This Delta deal was found by Cheapflights users on 3/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/14:24 pmMDW - PWM
1 stop7h 04mDelta
Thu 7/311:44 amPWM - MDW
1 stop7h 01mDelta
Deal found 3/31$233
This CheapOair deal was found by Cheapflights users on 3/31. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/91:19 pmMDW - PWM
1 stop28h 07mFrontier
Sun 5/118:23 pmPWM - MDW
1 stop17h 01mFrontier
Deal found 3/31$260
This Mytrip deal was found by Cheapflights users on 3/31. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/238:04 pmMDW - BOS
1 stop12h 08mAllegiant Air
Sun 5/2512:34 pmBOS - MDW
1 stop26h 30mAllegiant Air
Deal found 3/31$310
This Delta deal was found by Cheapflights users on 4/1. 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.
Sat 5/245:55 pmMDW - BOS
1 stop4h 01mDelta
Tue 5/275:20 amBOS - MDW
1 stop4h 20mDelta
Deal found 4/1$317
This Delta deal was found by Cheapflights users on 3/30. 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 9/69:30 amMDW - BGR
1 stop6h 05mDelta
Thu 9/116:00 amBGR - MDW
2 stops9h 54mDelta
Deal found 3/30$424

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 April 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 4/30

6:50 am-2:00 pm

1 stop6h 10m

Boston Logan Intl

Wed 5/7

3:00 pm-7:50 pm

1 stop5h 50m

$116

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Thu 5/8

1:19 pm-1:05 am

1 stop10h 46m

Boston Logan Intl

Mon 5/12

12:58 pm-11:47 pm

1 stop11h 49m

$198

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Mon 6/30

5:05 am-10:40 am

1 stop4h 35m

Portland

Thu 7/3

1:20 pm-5:25 pm

1 stop5h 05m

$229

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Tue 7/1

4:24 pm-12:28 am

1 stop7h 04m

Portland

Thu 7/3

11:44 am-5:45 pm

1 stop7h 01m

$233

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Fri 5/9

1:19 pm-6:26 pm

1 stop28h 07m

Portland

Sun 5/11

8:23 pm-12:24 pm

1 stop17h 01m

$260

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 5/23

8:04 pm-9:12 am

1 stop12h 08m

Boston Logan Intl

Sun 5/25

12:34 pm-2:04 pm

1 stop26h 30m

$310

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Sat 5/24

5:55 pm-10:56 pm

1 stop4h 01m

Boston Logan Intl

Tue 5/27

5:20 am-8:40 am

1 stop4h 20m

$317

ChicagoBangor

MDW - BGR

MDWBGR

Chicago Midway

Sat 9/6

9:30 am-4:35 pm

1 stop6h 05m

Bangor

Thu 9/11

6:00 am-2:54 pm

2 stops9h 54m

$424

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 6/4

2:40 pm-10:30 pm

1 stop6h 50m

$76

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Sun 4/20

2:19 pm-12:02 pm

1 stop20h 43m

$104

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/31

Showing 1-10 of 18 results
1
2

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 April 1, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago Midway Airport to Maine as you normally would.

Rainfall in Maine by month

Plan your trip to Maine by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Maine ranges from 2.9 - 4.5 inches per month. November is typically the wettest month, when rainfall can reach 4.5 in. August is typically the driest time to visit Maine when rainfall is around 2.9 in.

Temperature in Maine by month

Plan your trip to Maine by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Maine, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 68.0 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 April 1, 2025.
See what other customers who have flown with Southwest, Delta and Allegiant Air from Chicago to Maine have to say. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,277 reviews

Comfort

8.0

Entertainment

7.6

Food

7.1

Crew

8.7

Overall

8.0

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.0
Very good
4,277 reviews
Southwest
8.0
Very good
4,277 reviews

Comfort

8.0

Entertainment

7.6

Food

7.1

Crew

8.7

Overall

8.0

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,898 reviews
Southwest
8.0
Very good
4,277 reviews

Comfort

8.0

Entertainment

7.6

Food

7.1

Crew

8.7

Overall

8.0

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Allegiant Air
7.3
Good
731 reviews
Southwest
8.0
Very good
4,277 reviews

Comfort

8.0

Entertainment

7.6

Food

7.1

Crew

8.7

Overall

8.0

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Frontier
6.0
Okay
3,276 reviews
Southwest
8.0
Very good
4,277 reviews

Comfort

8.0

Entertainment

7.6

Food

7.1

Crew

8.7

Overall

8.0

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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.

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

    $76 is the cheapest one-way deal found within the past few days, from Southwest. You may also be able to find cheap deals on Allegiant Air and Frontier, with prices starting from $104 and $105, respectively.

  • 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.

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

    On average you can expect to pay $338 for a flight from Chicago Midway Airport to Maine. The cheapest flight overall is $174 while the most popular route, (Chicago Midway - Boston Logan Intl) is currently priced at $97.

  • 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.

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

    Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Maine (average of $296). Flying from Chicago Midway Airport to Maine in May is currently the most expensive (average of $416). 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

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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 April 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$191Average$406FlexibilityNo cancel feeOn-time63%
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