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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
ene. 22 — ene. 291
mié. 1/22
mié. 1/29
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 enero 17, 2025.

Round-trip from

$156
(Flightnetwork)

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 enero 17, 2025.

This Flightnetwork deal was found by Cheapflights users on 1/15. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 2/115:31 pmMDW - BOS
1 stop6h 08mFrontier
mié. 2/126:00 amBOS - MDW
1 stop18h 00mFrontier
Deal found 1/15$156
This Southwest deal was found by Cheapflights users on 1/14. 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.
mié. 1/2910:05 amMDW - BOS
Nonstop2h 15mSouthwest
dom. 2/27:00 amBOS - MDW
Nonstop2h 55mSouthwest
Deal found 1/14$157
This Gotogate deal was found by Cheapflights users on 1/16. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 2/1712:43 pmMDW - PWM
1 stop19h 35mFrontier
vie. 2/218:35 pmPWM - MDW
1 stop27h 16mFrontier
Deal found 1/16$206
This Delta deal was found by Cheapflights users on 1/16. 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.
sáb. 8/231:00 pmMDW - PWM
2 stops9h 45mDelta
sáb. 8/3011:59 amPWM - MDW
1 stop7h 04mDelta
Deal found 1/16$259
This Delta deal was found by Cheapflights users on 1/15. 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.
mié. 2/192:08 pmMDW - BGR
2 stops8h 10mDelta
mié. 2/266:00 amBGR - MDW
2 stops11h 20mDelta
Deal found 1/15$269
This Delta deal was found by Cheapflights users on 1/16. 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.
lun. 3/102:55 pmMDW - BOS
1 stop3h 59mDelta
jue. 3/135:30 amBOS - MDW
1 stop4h 15mDelta
Deal found 1/16$347
This Southwest deal was found by Cheapflights users on 1/15. 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.
lun. 8/251:50 pmMDW - PWM
Nonstop2h 15mSouthwest
dom. 8/317:55 pmPWM - MDW
Nonstop2h 35mSouthwest
Deal found 1/15$371
This Mytrip deal was found by Cheapflights users on 1/16. 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.
vie. 5/238:04 pmMDW - BOS
1 stop12h 08mAllegiant Air
lun. 5/269:00 amBOS - MDW
1 stop11h 14mAllegiant Air
Deal found 1/16$375
This eDestinos deal was found by Cheapflights users on 1/15. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 3/110:26 amMDW - PWM
2 stops21h 52mMultiple Airlines
sáb. 3/812:00 pmPWM - MDW
1 stop11h 40mMultiple Airlines
Deal found 1/15$425

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 enero 17, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

lun. 3/3

12:43 pm-12:44 am

1 stop11h 01m

Boston Logan Intl

vie. 3/7

10:41 am-9:25 pm

1 stop11h 44m

$154

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

mar. 2/4

6:25 pm-9:40 pm

Nonstop2h 15m

Boston Logan Intl

mar. 2/11

5:40 pm-7:30 pm

Nonstop2h 50m

$167

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

lun. 2/17

12:43 pm-9:18 am

1 stop19h 35m

Portland

vie. 2/21

8:35 pm-10:51 pm

1 stop27h 16m

$206

ChicagoBangor

MDW - BGR

MDWBGR

Chicago Midway

mié. 2/19

2:08 pm-11:18 pm

2 stops8h 10m

Bangor

mié. 2/26

6:00 am-4:20 pm

2 stops11h 20m

$269

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

dom. 3/2

6:28 pm-11:37 pm

1 stop4h 09m

Boston Logan Intl

dom. 3/9

5:30 am-8:45 am

1 stop4h 15m

$317

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

lun. 2/17

9:33 am-4:03 pm

1 stop5h 30m

Portland

vie. 2/21

6:00 am-5:43 pm

2 stops12h 43m

$320

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

vie. 6/13

8:36 pm-9:12 am

1 stop11h 36m

Boston Logan Intl

lun. 6/16

9:02 am-7:46 pm

1 stop11h 44m

$355

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

jue. 2/20

7:35 am-3:45 pm

1 stop7h 10m

Portland

lun. 2/24

1:25 pm-7:15 pm

1 stop6h 50m

$379

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

sáb. 3/1

10:26 am-9:18 am

2 stops21h 52m

Portland

sáb. 3/8

12:00 pm-10:40 pm

1 stop11h 40m

$425

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

vie. 4/11

8:46 am-6:22 pm

1 stop8h 36m

$65

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/16

Showing 1-10 of 19 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.

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 enero 17, 2025.
See what other customers who have flown with Southwest, Frontier and Delta 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
4,659 reviews

Food

7.2

Entertainment

7.7

Crew

8.7

Boarding

8.2

Overall

8.1

Comfort

8.1

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
4,659 reviews
Southwest
8.1
Very good
4,659 reviews

Food

7.2

Entertainment

7.7

Crew

8.7

Boarding

8.2

Overall

8.1

Comfort

8.1

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
8,511 reviews
Southwest
8.1
Very good
4,659 reviews

Food

7.2

Entertainment

7.7

Crew

8.7

Boarding

8.2

Overall

8.1

Comfort

8.1

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
3,435 reviews
Southwest
8.1
Very good
4,659 reviews

Food

7.2

Entertainment

7.7

Crew

8.7

Boarding

8.2

Overall

8.1

Comfort

8.1

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 $115, 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.

See more FAQs

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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 enero 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$191Average$333FlexibilityNo cancel feeOn-time63%
DeltaCheapest$196Average$342FlexibilityNo cancel feeOn-timeN/A