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$60+ 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 2/26. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MDW
Dec 30 — Jan 61
Mon 12/30
Mon 1/6
1 adult, Economy
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Cheap flight deals from Maine to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Maine (USME) to Midway (MDW). 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 December 25, 2024.

Round-trip from

$158
(Southwest)

One-way from

$60
(Mytrip)
From Maine to Chicago Midway
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One-way flight from Maine to Chicago Midway
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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 December 25, 2024.

This CheapOair deal was found by Cheapflights users on 12/24. 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.
Sat 12/285:45 amBOS - MDW
1 stop10h 26mFrontier
Wed 1/16:50 amMDW - BOS
1 stop27h 35mFrontier
Deal found 12/24$164
This Delta deal was found by Cheapflights users on 12/23. 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.
Tue 12/315:05 amPWM - MDW
1 stop4h 45mDelta
Sat 1/46:25 pmMDW - PWM
1 stop3h 57mDelta
Deal found 12/23$267
This Southwest deal was found by Cheapflights users on 12/23. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/312:00 pmBOS - MDW
1 stop5h 45mSouthwest
Sun 1/56:25 amMDW - BOS
Nonstop2h 15mSouthwest
Deal found 12/23$288
This Delta deal was found by Cheapflights users on 12/24. 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 12/285:25 amBOS - MDW
1 stop4h 25mDelta
Tue 12/314:50 pmMDW - BOS
1 stop6h 09mDelta
Deal found 12/24$342
This Southwest deal was found by Cheapflights users on 12/24. 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 12/316:00 amPWM - MDW
2 stops9h 30mSouthwest
Sat 1/47:15 amMDW - PWM
2 stops6h 15mSouthwest
Deal found 12/24$378
This Delta deal was found by Cheapflights users on 12/24. 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 12/297:00 amBGR - MDW
2 stops10h 17mDelta
Tue 1/72:08 pmMDW - BGR
2 stops8h 11mDelta
Deal found 12/24$893

Find flights from Maine to Midway within your budget

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 25, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 2/6

12:16 pm-12:09 pm

1 stop24h 53m

Chicago Midway

Mon 2/10

11:33 am-12:27 am

1 stop11h 54m

$138

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 1/17

7:00 am-8:55 am

Nonstop2h 55m

Chicago Midway

Tue 1/21

10:05 am-1:20 pm

Nonstop2h 15m

$158

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Tue 1/14

6:25 am-5:57 pm

2 stops36h 32m

Chicago Midway

Fri 1/17

3:37 pm-12:27 am

1 stop7h 50m

$165

PortlandChicago

PWM - MDW

PWMMDW

Portland

Wed 2/19

6:00 am-1:05 pm

2 stops8h 05m

Chicago Midway

Wed 2/26

9:33 am-4:03 pm

1 stop5h 30m

$233

PortlandChicago

PWM - MDW

PWMMDW

Portland

Wed 2/19

6:48 pm-10:46 pm

1 stop28h 58m

Chicago Midway

Mon 2/24

12:43 pm-9:18 am

1 stop19h 35m

$307

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Mon 1/13

5:20 am-8:54 am

1 stop4h 34m

Chicago Midway

Thu 1/16

2:08 pm-8:04 pm

1 stop4h 56m

$316

PortlandChicago

PWM - MDW

PWMMDW

Portland

Thu 1/16

1:25 pm-10:00 pm

1 stop9h 35m

Chicago Midway

Sun 1/19

8:10 am-3:00 pm

1 stop5h 50m

$333

BangorChicago

BGR - MDW

BGRMDW

Bangor

Sat 2/15

6:00 am-2:53 pm

2 stops9h 53m

Chicago Midway

Thu 2/20

2:08 pm-11:18 pm

2 stops8h 10m

$883

PortlandChicago

PWM - MDW

PWMMDW

Portland

Wed 2/26

6:48 pm-10:46 pm

1 stop28h 58m

$60

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 1/17

7:00 am-8:55 am

Nonstop2h 55m

$79

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/24

Showing 1-10 of 15 results
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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.

Travel insights for flights from Maine to Midway

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

Rainfall in Midway by month

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

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

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

If weather is an important factor for your trip to Chicago Midway Airport, 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 73.4 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 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 December 25, 2024.
Peruse reviews from past customers who have flown with Southwest, Frontier and Delta from Maine to Chicago to help guide your decision. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,758 reviews

Crew

8.7

Entertainment

7.7

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.2

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
4,758 reviews
Southwest
8.1
Very good
4,758 reviews

Crew

8.7

Entertainment

7.7

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.2

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
8,580 reviews
Southwest
8.1
Very good
4,758 reviews

Crew

8.7

Entertainment

7.7

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.2

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
3,465 reviews
Southwest
8.1
Very good
4,758 reviews

Crew

8.7

Entertainment

7.7

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.2

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 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 $60 on Frontier. Other airlines that offer cheap prices include Southwest from $79 and Delta from $114 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.

  • 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.

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Alternative routes for Maine to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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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 25, 2024.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$201Average$457FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$281Average$387FlexibilityNo cancel feeOn-time63%
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