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$68+ 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 2/3. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MDW
Feb 5 — Feb 121
Thu 2/5
Thu 2/12
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 January 6, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$125
(Delta)

One-way from

$68
(Southwest)

Popular in

December

Cheapest in

September

Average price

$352
Provider with most accurate pricing for Portland-Chicago (CHI) flight deals.
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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. 9% potential increase in price ($35 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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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 January 6, 2026.

This Delta deal was found by Cheapflights users on 1/5. 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 2/175:29 amBOS - MDW
1 stop4h 25mDelta
Wed 2/256:40 pmMDW - BOS
1 stop5h 29mDelta
Deal found 1/5$125
This Southwest deal was found by Cheapflights users on 1/4. 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.
Sat 1/244:55 pmBOS - MDW
Nonstop2h 50mSouthwest
Mon 1/265:35 pmMDW - BOS
Nonstop2h 15mSouthwest
Deal found 1/4$126
This Southwest deal was found by Cheapflights users on 1/5. 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 1/295:30 amBOS - MDW
Nonstop2h 50mSouthwest
Mon 2/22:00 pmMDW - BOS
Nonstop2h 10mSouthwest
Deal found 1/5$127
This Southwest deal was found by Cheapflights users on 1/4. 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.
Sat 1/174:55 pmBOS - MDW
Nonstop2h 50mSouthwest
Tue 1/205:35 pmMDW - BOS
Nonstop2h 15mSouthwest
Deal found 1/4$128
This Delta deal was found by Cheapflights users on 1/5. 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.
Thu 2/55:50 amBOS - MDW
1 stop8h 16mDelta
Mon 2/96:35 pmMDW - BOS
1 stop4h 16mDelta
Deal found 1/5$129
This Southwest deal was found by Cheapflights users on 1/5. 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 2/181:20 pmBOS - MDW
2 stops6h 15mSouthwest
Wed 2/256:00 amMDW - BOS
1 stop6h 40mSouthwest
Deal found 1/5$130
This Southwest deal was found by Cheapflights users on 1/5. 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 2/55:20 amBOS - MDW
Nonstop2h 50mSouthwest
Mon 2/96:35 pmMDW - BOS
Nonstop2h 15mSouthwest
Deal found 1/5$131
This Southwest deal was found by Cheapflights users on 1/5. 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.
Sat 1/105:30 amBOS - MDW
Nonstop2h 50mSouthwest
Sat 1/1710:15 amMDW - BOS
Nonstop2h 15mSouthwest
Deal found 1/5$133
This Southwest deal was found by Cheapflights users on 1/5. 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 2/41:20 pmBOS - MDW
2 stops6h 15mSouthwest
Wed 2/119:50 amMDW - BOS
1 stop5h 20mSouthwest
Deal found 1/5$134
This Southwest deal was found by Cheapflights users on 1/5. 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 1/295:30 amBOS - MDW
Nonstop2h 50mSouthwest
Sun 2/110:45 amMDW - BOS
1 stop4h 30mSouthwest
Deal found 1/5$136
This Delta deal was found by Cheapflights users on 1/6. 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 2/182:35 pmPWM - MDW
2 stops8h 56mDelta
Wed 2/2512:45 pmMDW - PWM
2 stops9h 35mDelta
Deal found 1/6$208
This Delta deal was found by Cheapflights users on 1/5. 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 3/912:51 pmPWM - MDW
1 stop6h 03mDelta
Wed 3/111:10 pmMDW - PWM
2 stops9h 12mDelta
Deal found 1/5$209

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 January 6, 2026.
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

Thu 1/29

5:30 am-7:20 am

Nonstop2h 50m

Chicago Midway

Mon 2/2

2:00 pm-5:10 pm

Nonstop2h 10m

$127

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Mon 2/9

9:00 am-12:46 pm

1 stop4h 46m

Chicago Midway

Tue 2/17

1:28 pm-7:58 pm

1 stop5h 30m

$127

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sat 1/31

5:30 am-7:20 am

Nonstop2h 50m

Chicago Midway

Mon 2/2

2:00 pm-5:10 pm

Nonstop2h 10m

$127

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 1/29

5:30 am-7:20 am

Nonstop2h 50m

Chicago Midway

Sun 2/1

10:45 am-4:15 pm

1 stop4h 30m

$136

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sat 1/31

12:55 pm-4:55 pm

1 stop5h 00m

Chicago Midway

Sun 2/1

9:40 am-12:55 pm

Nonstop2h 15m

$137

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 1/23

5:30 am-7:20 am

Nonstop2h 50m

Chicago Midway

Mon 1/26

5:35 pm-8:50 pm

Nonstop2h 15m

$137

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Mon 1/12

5:50 am-1:55 pm

2 stops9h 05m

Chicago Midway

Sat 1/17

10:15 am-1:30 pm

Nonstop2h 15m

$144

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sat 1/17

2:50 pm-7:00 pm

1 stop5h 10m

Chicago Midway

Tue 1/20

1:50 pm-9:25 pm

1 stop6h 35m

$145

PortlandChicago

PWM - MDW

PWMMDW

Portland

Mon 3/9

12:51 pm-5:54 pm

1 stop6h 03m

Chicago Midway

Wed 3/11

1:10 pm-11:22 pm

2 stops9h 12m

$209

PortlandChicago

PWM - MDW

PWMMDW

Portland

Wed 4/8

5:18 am-12:02 pm

1 stop7h 44m

Chicago Midway

Sun 4/12

9:35 am-4:06 pm

1 stop5h 31m

$213

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/5

Showing 1-10 of 46 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.

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 January 6, 2026.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 12% on flights from Maine to Chicago Midway Airport by exploring options for tickets in the morning.

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.

  • How long is the flight from Maine to Chicago Midway Airport?

    For as low as $127, Southwest can have you in Chicago Midway Airport from Maine in 2h 50m. The distance between Maine and Chicago Midway Airport is about 857 mi. This flight may include one or multiple stops.

  • 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.

See more FAQs

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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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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Philadelphia to Midway flights
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Miami to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
Cleveland to O'Hare Intl flights
Orlando to Midway flights
Denver to Midway flights
Reagan-National to Midway flights
Tampa to Midway flights
San Francisco to Midway flights
Detroit to O'Hare Intl flights
Sky Harbor Intl to Midway flights
Portland to O'Hare Intl flights
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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 January 6, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$246Average$397FlexibilityNo cancel feeOn-time63%
DeltaCheapest$253Average$327FlexibilityNo cancel feeOn-timeN/A

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