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Maine

$59+ Cheap flights from Wisconsin 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 1/20. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — PWM
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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Cheap flight deals from Wisconsin to Maine

Keep the following information in mind while searching for Wisconsin to Maine flight deals. Data was last updated October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$117
(Delta)

One-way from

$59
(Delta)

Popular in

December

Cheapest in

April

Average price

$452
Provider with most accurate pricing for Milwaukee-Mitchell-Portland flight deals.
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Provider most trusted by Cheapflights users for Milwaukee-Mitchell-Portland flights.
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From Wisconsin to Maine
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One-way flight from Wisconsin to Maine
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Highest demand for flights based on searches. 22% potential increase in price ($117 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Find flight deals from Wisconsin to Maine

Cheapest flights from Wisconsin to Maine
Explore the most affordable flight options available from Wisconsin to Maine. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 30, 2025.

This Delta deal was found by Cheapflights users on 10/29. 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.
Fri 12/57:10 pmORD - BOS
Nonstop2h 24mDelta
Mon 12/87:52 pmBOS - ORD
Nonstop2h 55mDelta
Deal found 10/29$117
This Delta deal was found by Cheapflights users on 10/29. 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 12/47:10 amORD - BOS
Nonstop2h 26mDelta
Sun 12/77:30 amBOS - ORD
Nonstop3h 03mDelta
Deal found 10/29$118
This Mytrip deal was found by Cheapflights users on 10/29. 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 11/135:25 amORD - BOS
1 stop26h 03mFrontier
Mon 11/178:40 amBOS - ORD
1 stop15h 48mFrontier
Deal found 10/29$119
This American Airlines deal was found by Cheapflights users on 10/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/183:08 pmORD - BOS
Nonstop2h 21mAmerican Airlines
Sat 12/66:00 amBOS - ORD
Nonstop3h 17mAmerican Airlines
Deal found 10/30$122
This American Airlines deal was found by Cheapflights users on 10/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/155:12 pmORD - BOS
Nonstop2h 21mAmerican Airlines
Thu 1/15:30 pmBOS - ORD
Nonstop3h 14mAmerican Airlines
Deal found 10/29$124
This Trip.com deal was found by Cheapflights users on 10/29. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/56:55 pmORD - BOS
Nonstop2h 32mJetBlue
Wed 11/128:30 amBOS - ORD
Nonstop3h 05mJetBlue
Deal found 10/29$125
This JetBlue deal was found by Cheapflights users on 10/29. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/611:20 amORD - BOS
Nonstop2h 24mJetBlue
Wed 11/123:55 pmBOS - ORD
Nonstop3h 00mJetBlue
Deal found 10/29$127
This Trip.com deal was found by Cheapflights users on 10/30. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1311:20 amORD - BOS
Nonstop2h 24mJetBlue
Mon 11/173:55 pmBOS - ORD
Nonstop3h 00mJetBlue
Deal found 10/30$128
This Delta deal was found by Cheapflights users on 10/30. 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 11/277:45 amORD - BOS
Nonstop2h 24mDelta
Fri 12/57:52 pmBOS - ORD
Nonstop2h 55mDelta
Deal found 10/30$129
This JetBlue deal was found by Cheapflights users on 10/29. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1311:20 amORD - BOS
Nonstop2h 24mJetBlue
Wed 11/198:30 amBOS - ORD
Nonstop3h 05mJetBlue
Deal found 10/29$130
This United Airlines deal was found by Cheapflights users on 10/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/189:20 amORD - BOS
Nonstop2h 33mUnited Airlines
Sun 12/216:23 pmBOS - ORD
Nonstop3h 02mUnited Airlines
Deal found 10/30$131
This Kiwi.com deal was found by Cheapflights users on 10/30. 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.
Thu 12/1110:34 amMKE - BOS
1 stop22h 23mMultiple Airlines
Sun 12/1412:57 pmBOS - MKE
1 stop21h 42mMultiple Airlines
Deal found 10/30$191

Cheapflights Fare Finder

 
Customize your flight search to find flights from Wisconsin 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 October 30, 2025.
Use the filters below to find and compare flights from Wisconsin to Maine that are best for you.

Fly from

Wisconsin

Fly to

Maine

Route

Depart

Return

Price

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 12/5

7:30 am-10:49 am

Nonstop2h 19m

Boston Logan Intl

Mon 12/8

6:00 am-8:00 am

Nonstop3h 00m

$117

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 12/13

7:10 am-10:36 am

Nonstop2h 26m

Boston Logan Intl

Sun 12/14

4:05 pm-6:02 pm

Nonstop2h 57m

$117

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 12/4

7:10 am-10:36 am

Nonstop2h 26m

Boston Logan Intl

Sun 12/7

4:05 pm-6:02 pm

Nonstop2h 57m

$117

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 12/10

10:35 am-1:59 pm

Nonstop2h 24m

Boston Logan Intl

Sat 12/13

7:30 am-9:33 am

Nonstop3h 03m

$117

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 12/5

7:10 pm-10:34 pm

Nonstop2h 24m

Boston Logan Intl

Mon 12/8

7:52 pm-9:47 pm

Nonstop2h 55m

$117

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 12/6

10:35 am-1:59 pm

Nonstop2h 24m

Boston Logan Intl

Sun 12/7

12:50 pm-2:47 pm

Nonstop2h 57m

$117

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 12/16

7:10 am-10:36 am

Nonstop2h 26m

Boston Logan Intl

Tue 12/16

4:05 pm-6:02 pm

Nonstop2h 57m

$117

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 11/14

6:55 pm-10:27 pm

Nonstop2h 32m

Boston Logan Intl

Mon 11/17

3:55 pm-5:55 pm

Nonstop3h 00m

$127

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 12/18

9:20 am-12:53 pm

Nonstop2h 33m

Boston Logan Intl

Sun 12/21

4:15 pm-6:19 pm

Nonstop3h 04m

$131

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 1/15

10:45 am-2:09 pm

Nonstop2h 24m

Boston Logan Intl

Sat 1/17

3:35 pm-5:44 pm

Nonstop3h 09m

$132

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/30

Showing 1-10 of 60 results
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Best time to book a flight from Wisconsin to Maine

Have a flexible travel schedule? Discover the best time to fly to Maine from Wisconsin 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 Wisconsin to Maine

What is the cheapest month to book a flight from Wisconsin to Maine?

Currently, March is the cheapest month in which you can book a flight from Wisconsin to Maine (average of $219). Flying from Wisconsin to Maine in July is currently the most expensive (average of $270). 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.

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 October 30, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, and United Airlines from Wisconsin to Maine to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,243 reviews

Crew

8.6

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,243 reviews
Southwest
8.0
Very good
4,243 reviews

Crew

8.6

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
7.9
Good
7,998 reviews
Southwest
8.0
Very good
4,243 reviews

Crew

8.6

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,998 reviews
Southwest
8.0
Very good
4,243 reviews

Crew

8.6

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
11,035 reviews
Southwest
8.0
Very good
4,243 reviews

Crew

8.6

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

Find useful and relevant information for your journey from Wisconsin to Maine. 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 Wisconsin to Maine?

    Airlines like United Airlines, Delta, and Sun Country Air fly from Wisconsin to Maine in about 2h 19m. The time it takes to get you to your destination is usually consistent. The distance from Wisconsin to Maine is about 864 mi. All flights are typically nonstop.

  • What are the cheapest airlines to fly from Wisconsin to Maine one-way?

    For one-way options, check prices for Delta. According to our data, you can fly for as low as $59. Users have also found prices from $65 and $69 on JetBlue and United Airlines, respectively.

  • Can I find deals for flights from Wisconsin to Maine that include hotel bookings?

    Yes. In addition to deals on Wisconsin to Maine flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Wisconsin to Maine?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Wisconsin to Maine.

  • Can I find deals for business class flights from Wisconsin to Maine?

    Yes. Cheapflights offers flight deals from Wisconsin 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 Wisconsin to Maine?

    Currently, March is the cheapest month in which you can book a flight from Wisconsin to Maine (average of $219). Flying from Wisconsin to Maine in July is currently the most expensive (average of $270). 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 Wisconsin to Maine

See prices for flight routes from nearby airports that may be better suited for you.
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Top 4 airlines flying from Wisconsin to Maine

Discover the top 4 airlines that operate flights from Wisconsin 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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$238Average$465FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$246Average$388FlexibilityNo cancel feeOn-time63%
DeltaCheapest$248Average$380FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$267Average$428FlexibilityNo cancel feeOn-time69%

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