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Midway

$59+ 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 5/29. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MDW
Apr 29 — May 61
Tue 4/29
Tue 5/6
1 adult, Economy
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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 April 24, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$127
(Southwest)

One-way from

$59
(Southwest)

Popular in

November

Cheapest in

September

Average price

$356

Good round-trip deal

$362 or less

Good one-way deal

$178 or less
Provider with most accurate pricing for Portland-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Portland-Chicago (CHI) flights.
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From Maine to Chicago Midway
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One-way flight from Maine to Chicago Midway
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Highest demand for flights based on searches. 11% potential increase in price ($45 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($8 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 Maine to Chicago Midway.
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Price to beat on a 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 April 24, 2025.

This Southwest deal was found by Cheapflights users on 4/23. 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.
Wed 5/285:35 amBOS - MDW
1 stop7h 05mSouthwest
Sun 6/16:50 amMDW - BOS
Nonstop2h 15mSouthwest
Deal found 4/23$127
This Frontier deal was found by Cheapflights users on 4/23. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/299:23 amBOS - MDW
1 stop14h 18mFrontier
Sun 6/19:12 pmMDW - BOS
1 stop10h 23mFrontier
Deal found 4/23$198
This Southwest deal was found by Cheapflights users on 4/23. 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.
Wed 7/306:55 pmPWM - MDW
Nonstop2h 35mSouthwest
Tue 8/511:40 amMDW - PWM
Nonstop2h 15mSouthwest
Deal found 4/23$219
This Booking.com deal was found by Cheapflights users on 4/23. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/19:29 pmPWM - MDW
1 stop15h 55mFrontier
Sun 5/410:55 amMDW - PWM
1 stop7h 38mFrontier
Deal found 4/23$228
This Delta deal was found by Cheapflights users on 4/23. 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.
Wed 5/215:30 amPWM - MDW
1 stop7h 23mDelta
Wed 5/284:15 pmMDW - PWM
1 stop6h 44mDelta
Deal found 4/23$239
This Mytrip deal was found by Cheapflights users on 4/22. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2211:31 amBOS - MDW
1 stop25h 54mAllegiant Air
Mon 5/262:54 pmMDW - BOS
1 stop17h 20mAllegiant Air
Deal found 4/22$255
This Mytrip deal was found by Cheapflights users on 4/23. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/69:02 amBOS - MDW
1 stop11h 44mMultiple Airlines
Mon 6/98:36 pmMDW - BOS
3 stops35h 33mMultiple Airlines
Deal found 4/23$275
This Delta deal was found by Cheapflights users on 4/22. 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.
Wed 7/25:10 amBOS - MDW
1 stop8h 19mDelta
Tue 7/85:59 pmMDW - BOS
1 stop4h 34mDelta
Deal found 4/22$285
This Delta deal was found by Cheapflights users on 4/23. 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.
Sat 6/72:05 pmBGR - MDW
1 stop8h 08mDelta
Sat 6/149:24 amMDW - BGR
2 stops10h 51mDelta
Deal found 4/23$314

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 April 24, 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

Wed 5/28

5:35 am-11:40 am

1 stop7h 05m

Chicago Midway

Sun 6/1

6:50 am-10:05 am

Nonstop2h 15m

$127

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 5/29

9:23 am-10:41 pm

1 stop14h 18m

Chicago Midway

Sun 6/1

9:12 pm-8:35 am

1 stop10h 23m

$198

PortlandChicago

PWM - MDW

PWMMDW

Portland

Wed 7/30

6:55 pm-8:30 pm

Nonstop2h 35m

Chicago Midway

Tue 8/5

11:40 am-2:55 pm

Nonstop2h 15m

$219

PortlandChicago

PWM - MDW

PWMMDW

Portland

Wed 5/21

5:30 am-11:53 am

1 stop7h 23m

Chicago Midway

Wed 5/28

1:55 pm-11:59 pm

2 stops9h 04m

$228

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 5/22

11:31 am-12:25 pm

1 stop25h 54m

Chicago Midway

Mon 5/26

2:54 pm-9:14 am

1 stop17h 20m

$255

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 6/6

9:02 am-7:46 pm

1 stop11h 44m

Chicago Midway

Mon 6/9

8:36 pm-9:09 am

3 stops35h 33m

$275

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 7/2

5:10 am-12:29 pm

1 stop8h 19m

Chicago Midway

Tue 7/8

5:59 pm-11:33 pm

1 stop4h 34m

$285

BangorChicago

BGR - MDW

BGRMDW

Bangor

Sat 6/7

2:05 pm-9:13 pm

1 stop8h 08m

Chicago Midway

Sat 6/14

9:24 am-9:15 pm

2 stops10h 51m

$314

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 5/29

5:45 am-7:20 am

Nonstop2h 35m

$59

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sun 6/8

11:31 am-7:15 am

1 stop20h 44m

$93

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/23

Showing 1-10 of 18 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 April 24, 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.

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 April 24, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta and Allegiant Air 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
8.0
Very good
4,286 reviews

Boarding

8.2

Overall

8.0

Crew

8.6

Entertainment

7.6

Comfort

8.0

Food

7.1

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
4,286 reviews
Southwest
8.0
Very good
4,286 reviews

Boarding

8.2

Overall

8.0

Crew

8.6

Entertainment

7.6

Comfort

8.0

Food

7.1

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
7,920 reviews
Southwest
8.0
Very good
4,286 reviews

Boarding

8.2

Overall

8.0

Crew

8.6

Entertainment

7.6

Comfort

8.0

Food

7.1

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
4,286 reviews

Boarding

8.2

Overall

8.0

Crew

8.6

Entertainment

7.6

Comfort

8.0

Food

7.1

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
3,283 reviews
Southwest
8.0
Very good
4,286 reviews

Boarding

8.2

Overall

8.0

Crew

8.6

Entertainment

7.6

Comfort

8.0

Food

7.1

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 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 $59 on Southwest. Other airlines that offer cheap prices include Allegiant Air from $93 and Frontier from $95 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 $310, our data shows the cheapest flight currently is $144. When looking at the most popular route, (Boston Logan Intl - Chicago Midway), you can expect to pay $117 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
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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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 April 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$201Average$327FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$264Average$379FlexibilityNo cancel feeOn-time63%

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