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$65+ 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 4/11. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PWM
Jan 29 — Feb 51
Wed 1/29
Wed 2/5
1 adult, Economy
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Cheap flight deals from Midway to Maine

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Maine (USME). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 24, 2025.

Round-trip from

$154
(CheapOair)

One-way from

$65
(Frontier)
From Chicago Midway to Maine
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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 January 24, 2025.

This CheapOair deal was found by Cheapflights users on 1/23. 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 3/72:41 pmMDW - BOS
1 stop16h 40mFrontier
Mon 3/105:10 amBOS - MDW
1 stop7h 24mFrontier
Deal found 1/23$154
This Southwest deal was found by Cheapflights users on 1/22. 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 2/168:05 amMDW - BOS
Nonstop2h 15mSouthwest
Sun 2/236:50 amBOS - MDW
Nonstop2h 55mSouthwest
Deal found 1/22$157
This FlightHub deal was found by Cheapflights users on 1/23. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/111:05 pmMDW - PWM
1 stop19h 07mFrontier
Tue 4/153:05 pmPWM - MDW
1 stop9h 19mFrontier
Deal found 1/23$233
This Delta deal was found by Cheapflights users on 1/23. 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.
Sun 3/96:42 pmMDW - PWM
1 stop3h 32mDelta
Sun 3/167:00 amPWM - MDW
1 stop6h 36mDelta
Deal found 1/23$254
This Delta deal was found by Cheapflights users on 1/22. 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 2/242:08 pmMDW - BGR
2 stops8h 10mDelta
Wed 3/56:00 amBGR - MDW
2 stops11h 20mDelta
Deal found 1/22$259
This Southwest deal was found by Cheapflights users on 1/22. 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 2/45:05 pmMDW - PWM
1 stop4h 10mSouthwest
Sat 2/812:55 pmPWM - MDW
1 stop6h 30mSouthwest
Deal found 1/22$279
This Delta deal was found by Cheapflights users on 1/22. 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 2/49:33 amMDW - BOS
1 stop5h 20mDelta
Thu 2/135:20 amBOS - MDW
1 stop8h 45mDelta
Deal found 1/22$305

Find flights from Midway to Maine within your budget

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 January 24, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 2/19

10:05 am-1:20 pm

Nonstop2h 15m

Boston Logan Intl

Sun 2/23

6:50 am-8:45 am

Nonstop2h 55m

$157

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Thu 5/15

4:00 pm-9:34 am

1 stop16h 34m

Boston Logan Intl

Mon 5/19

12:48 pm-11:39 pm

1 stop11h 51m

$158

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Fri 4/11

1:05 pm-9:12 am

1 stop19h 07m

Portland

Tue 4/15

3:05 pm-11:24 pm

1 stop9h 19m

$233

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Sun 3/9

6:42 pm-11:14 pm

1 stop3h 32m

Portland

Sun 3/16

7:00 am-12:36 pm

1 stop6h 36m

$254

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Tue 2/4

5:05 pm-10:15 pm

1 stop4h 10m

Portland

Sat 2/8

12:55 pm-6:25 pm

1 stop6h 30m

$279

ChicagoBangor

MDW - BGR

MDWBGR

Chicago Midway

Fri 2/7

12:44 pm-11:18 pm

2 stops9h 34m

Bangor

Tue 2/11

6:00 am-4:20 pm

2 stops11h 20m

$299

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 2/21

6:28 pm-11:37 pm

1 stop4h 09m

Boston Logan Intl

Sat 3/1

9:15 am-4:09 pm

1 stop7h 54m

$315

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Fri 4/11

8:46 am-6:22 pm

1 stop8h 36m

$65

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Sun 2/16

8:20 pm-11:35 pm

Nonstop2h 15m

$79

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Thu 4/3

10:19 am-12:47 am

1 stop13h 28m

$81

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/23

Showing 1-10 of 17 results
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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.

Travel insights for flights from Midway to Maine

Get recent, data-driven insights about flights from Midway to Maine including ideal travel times, pricing trends, and more.

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 January 24, 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 January 24, 2025.
See what other customers who have flown with Southwest, Delta and Frontier 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
8.1
Very good
4,647 reviews

Comfort

8.1

Food

7.2

Overall

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,647 reviews
Southwest
8.1
Very good
4,647 reviews

Comfort

8.1

Food

7.2

Overall

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,508 reviews
Southwest
8.1
Very good
4,647 reviews

Comfort

8.1

Food

7.2

Overall

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Allegiant Air
7.4
Good
799 reviews
Southwest
8.1
Very good
4,647 reviews

Comfort

8.1

Food

7.2

Overall

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Frontier
6.1
Okay
3,440 reviews
Southwest
8.1
Very good
4,647 reviews

Comfort

8.1

Food

7.2

Overall

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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?

    $65 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on Southwest and Delta, with prices starting from $79 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.

  • 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 April is currently the most expensive (average of $498). 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.

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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 2 airlines flying from Midway to Maine

Discover the top 2 airlines 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 January 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$191Average$364FlexibilityNo cancel feeOn-time63%
DeltaCheapest$196Average$342FlexibilityNo cancel feeOn-timeN/A
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