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Midway

$63+ 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 1/19. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MDW
nov 20 — nov 271
tors 11/20
tors 11/27
1 adult, Economy
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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 oktober 21, 2025.

This Southwest deal was found by Cheapflights users on 10/19. 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.
mån 12/85:30 amBOS - MDW
Nonstop2h 45mSouthwest
sön 1/255:50 amMDW - BOS
1 stop4h 30mSouthwest
Deal found 10/19$119
This Southwest deal was found by Cheapflights users on 10/20. 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.
tis 12/95:30 amBOS - MDW
Nonstop2h 45mSouthwest
lör 12/139:50 amMDW - BOS
Nonstop2h 20mSouthwest
Deal found 10/20$125
This Southwest deal was found by Cheapflights users on 10/21. 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.
lör 11/15:20 amBOS - MDW
Nonstop2h 40mSouthwest
ons 11/196:15 pmMDW - BOS
Nonstop2h 20mSouthwest
Deal found 10/21$127
This Southwest deal was found by Cheapflights users on 10/19. 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.
lör 11/15:20 amBOS - MDW
Nonstop2h 40mSouthwest
tis 11/42:30 pmMDW - BOS
2 stops6h 45mSouthwest
Deal found 10/19$132
This Southwest deal was found by Cheapflights users on 10/19. 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.
fre 11/146:55 pmBOS - MDW
Nonstop2h 50mSouthwest
mån 11/176:40 amMDW - BOS
1 stop8h 55mSouthwest
Deal found 10/19$133
This Southwest deal was found by Cheapflights users on 10/20. 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.
tors 12/45:30 amBOS - MDW
Nonstop2h 45mSouthwest
mån 12/86:15 pmMDW - BOS
Nonstop2h 20mSouthwest
Deal found 10/20$134
This Southwest deal was found by Cheapflights users on 10/19. 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.
lör 12/135:20 amBOS - MDW
Nonstop2h 45mSouthwest
ons 12/176:15 pmMDW - BOS
Nonstop2h 20mSouthwest
Deal found 10/19$136
This Delta deal was found by Cheapflights users on 10/21. 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.
tors 12/45:29 amBOS - MDW
1 stop4h 25mDelta
mån 12/89:34 amMDW - BOS
1 stop5h 29mDelta
Deal found 10/21$137
This KAYAK deal was found by Cheapflights users on 10/20. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ons 11/121:35 pmBOS - MDW
Nonstop2h 45mSouthwest
tors 11/136:20 amMDW - BOS
3 stops13h 25mSouthwest
Deal found 10/20$138
This Kiwi.com deal was found by Cheapflights users on 10/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
tors 11/137:43 pmBGR - MDW
1 stop27h 27mMultiple Airlines
mån 11/176:06 pmMDW - BGR
1 stop22h 50mMultiple Airlines
Deal found 10/20$202
This Kiwi.com deal was found by Cheapflights users on 10/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ons 11/126:29 pmBGR - MDW
1 stop15h 43mMultiple Airlines
mån 11/176:06 pmMDW - BGR
1 stop22h 50mMultiple Airlines
Deal found 10/20$204
This Kiwi.com deal was found by Cheapflights users on 10/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ons 11/126:29 pmBGR - MDW
1 stop15h 43mMultiple Airlines
sön 11/166:06 pmMDW - BGR
1 stop23h 04mMultiple Airlines
Deal found 10/20$205

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 oktober 21, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$119
(Southwest)

One-way from

$63
(Southwest)

Popular in

April

Cheapest in

September

Average price

$247

Good round-trip deal

$377 or less

Good one-way deal

$206 or less
Provider with most accurate pricing for Boston Logan Intl-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Boston Logan Intl-Chicago (CHI) flights.
Search Deals
From Maine to Chicago Midway
Search Deals
One-way flight from Maine to Chicago Midway
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($22 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 0% potential price decrease ($3 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals
Price to beat on a round-trip flight from Maine to Chicago Midway.
Search Deals
Price to beat on a one-way flight from Maine to Chicago Midway.
Search Deals

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 oktober 21, 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

tors 11/13

6:55 pm-8:45 pm

Nonstop2h 50m

Chicago Midway

lör 11/15

9:50 am-1:10 pm

Nonstop2h 20m

$127

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

tis 11/4

5:30 am-7:15 am

Nonstop2h 45m

Chicago Midway

tis 11/4

2:30 pm-10:15 pm

2 stops6h 45m

$132

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

lör 11/1

8:15 am-11:40 am

1 stop4h 25m

Chicago Midway

tors 11/6

5:15 pm-10:55 pm

1 stop4h 40m

$137

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

tis 10/28

5:40 pm-10:05 pm

1 stop5h 25m

Chicago Midway

ons 10/29

1:15 pm-4:30 pm

Nonstop2h 15m

$137

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

tis 11/4

9:05 am-6:25 pm

2 stops10h 20m

Chicago Midway

tors 11/6

5:15 pm-10:55 pm

1 stop4h 40m

$142

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

ons 11/5

5:45 am-10:10 am

1 stop5h 25m

Chicago Midway

tors 11/6

6:45 am-6:10 pm

1 stop10h 25m

$142

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

lör 11/8

5:55 am-4:45 pm

1 stop11h 50m

Chicago Midway

ons 11/12

9:20 am-4:35 pm

1 stop6h 15m

$142

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

ons 10/29

6:45 am-1:35 pm

1 stop7h 50m

Chicago Midway

ons 11/5

12:55 pm-7:20 pm

1 stop5h 25m

$147

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

fre 12/5

5:30 am-7:15 am

Nonstop2h 45m

Chicago Midway

mån 12/8

6:15 pm-9:35 pm

Nonstop2h 20m

$155

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

ons 11/19

5:30 am-7:15 am

Nonstop2h 45m

Chicago Midway

sön 11/23

7:15 pm-10:30 pm

Nonstop2h 15m

$177

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/20

Showing 1-10 of 54 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 oktober 21, 2025.

Unlike in the evening, when flights are generally more expensive, you can save up to 31% 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.

  • What are the cheapest flights from Maine to Chicago Midway Airport?

    While on average a flight from Maine to Chicago Midway Airport is generally $418, our data shows the cheapest flight currently is $206. When looking at the most popular route, (Boston Logan Intl - Chicago Midway), you can expect to pay $100 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.

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
Merrillville
Lansing
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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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 oktober 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$246Average$390FlexibilityNo cancel feeOn-time63%
DeltaCheapest$253Average$327FlexibilityNo cancel feeOn-timeN/A

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