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$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 5/9. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PWM
May 4 — May 111
Sun 5/4
Sun 5/11
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 29, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$117
(Southwest)

One-way from

$59
(Southwest)

Popular in

April

Cheapest in

February

Average price

$479

Good round-trip deal

$400 or less
Provider with most accurate pricing for Chicago (CHI)-Portland flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Portland flights.
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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. 4% potential increase in price ($18 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($12 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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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 29, 2025.

This Southwest deal was found by Cheapflights users on 4/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/95:30 amMDW - BOS
Nonstop2h 15mSouthwest
Sun 5/117:40 amBOS - MDW
Nonstop2h 35mSouthwest
Deal found 4/29$117
This Mytrip deal was found by Cheapflights users on 4/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/139:12 amMDW - BOS
1 stop25h 49mAllegiant Air
Sun 6/1511:31 amBOS - MDW
1 stop20h 44mAllegiant Air
Deal found 4/29$208
This CheapOair deal was found by Cheapflights users on 4/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/121:19 pmMDW - BOS
1 stop10h 25mFrontier
Wed 5/148:00 amBOS - MDW
1 stop29h 24mFrontier
Deal found 4/29$211
This Delta deal was found by Cheapflights users on 4/29. 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.
Sat 5/244:15 pmMDW - PWM
1 stop6h 44mDelta
Sun 5/256:05 amPWM - MDW
2 stops7h 23mDelta
Deal found 4/29$254
This Southwest deal was found by Cheapflights users on 4/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/215:40 amMDW - PWM
1 stop6h 35mSouthwest
Sun 8/245:35 amPWM - MDW
2 stops11h 00mSouthwest
Deal found 4/29$260
This Delta deal was found by Cheapflights users on 4/29. 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 5/286:25 pmMDW - BOS
1 stop4h 21mDelta
Fri 5/305:20 amBOS - MDW
1 stop4h 20mDelta
Deal found 4/29$317
This Delta deal was found by Cheapflights users on 4/29. 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.
Mon 8/181:05 pmMDW - BGR
2 stops9h 24mDelta
Sat 8/232:00 pmBGR - MDW
1 stop8h 47mDelta
Deal found 4/29$349

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 29, 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

Fri 5/9

5:30 am-8:45 am

Nonstop2h 15m

Boston Logan Intl

Sun 5/11

7:40 am-9:15 am

Nonstop2h 35m

$117

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 6/13

9:12 am-12:01 pm

1 stop25h 49m

Boston Logan Intl

Sun 6/15

11:31 am-7:15 am

1 stop20h 44m

$208

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Mon 5/12

1:19 pm-12:44 am

1 stop10h 25m

Boston Logan Intl

Wed 5/14

8:00 am-12:24 pm

1 stop29h 24m

$211

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Sat 5/24

4:15 pm-11:59 pm

1 stop6h 44m

Portland

Sun 5/25

6:05 am-12:28 pm

2 stops7h 23m

$254

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Thu 8/21

5:40 am-1:15 pm

1 stop6h 35m

Portland

Sun 8/24

5:35 am-3:35 pm

2 stops11h 00m

$260

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Tue 7/1

4:26 pm-1:21 am

1 stop7h 55m

Boston Logan Intl

Sun 7/6

5:10 am-8:41 am

1 stop4h 31m

$316

ChicagoBangor

MDW - BGR

MDWBGR

Chicago Midway

Wed 6/25

12:44 pm-11:21 pm

2 stops9h 37m

Bangor

Mon 6/30

2:40 pm-9:45 pm

1 stop8h 05m

$504

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 5/9

5:30 am-8:45 am

Nonstop2h 15m

$59

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 6/13

9:12 am-12:01 pm

1 stop25h 49m

$98

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Tue 8/26

11:40 am-2:55 pm

Nonstop2h 15m

$105

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Showing 1-10 of 17 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 29, 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 29, 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
4,295 reviews

Crew

8.6

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,295 reviews
Southwest
8.0
Very good
4,295 reviews

Crew

8.6

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,936 reviews
Southwest
8.0
Very good
4,295 reviews

Crew

8.6

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Allegiant Air
7.3
Good
734 reviews
Southwest
8.0
Very good
4,295 reviews

Crew

8.6

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Frontier
6.0
Okay
3,287 reviews
Southwest
8.0
Very good
4,295 reviews

Crew

8.6

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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?

    $59 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 Delta, with prices starting from $98 and $109, 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 $435 for a flight from Chicago Midway Airport to Maine. The cheapest flight overall is $279 while the most popular route, (Chicago Midway - Boston Logan Intl) is currently priced at $117.

  • 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 $405). 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 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$191Average$406FlexibilityNo cancel feeOn-time63%

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