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Wisconsin

$68+ Cheap flights from Maine to Wisconsin

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 2/6. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MKE
Feb 20 — Feb 271
Fri 2/20
Fri 2/27
1 adult, Economy
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Cheap flight deals from Maine to Wisconsin

Cheapest flights from Maine to Wisconsin
Explore the most affordable flight options available from Maine to Wisconsin. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 21, 2026.

This JetBlue deal was found by Cheapflights users on 1/19. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/112:50 pm
BOS
-
ORD
Nonstop3h 05m
JetBlue
Sun 2/156:04 am
ORD
-
BOS
1 stop7h 20m
JetBlue
Deal found 1/19$132
This Expedia deal was found by Cheapflights users on 1/20. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/63:35 pm
BOS
-
ORD
Nonstop3h 08m
Multiple Airlines
Tue 2/106:07 pm
ORD
-
BOS
1 stop6h 06m
Multiple Airlines
Deal found 1/20$133
This American Airlines deal was found by Cheapflights users on 1/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/285:54 pm
BOS
-
ORD
Nonstop3h 06m
American Airlines
Sun 3/16:26 am
ORD
-
BOS
Nonstop2h 28m
American Airlines
Deal found 1/20$134
This United Airlines deal was found by Cheapflights users on 1/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/296:00 am
BOS
-
ORD
Nonstop3h 04m
United Airlines
Thu 1/294:15 pm
ORD
-
BOS
Nonstop2h 24m
United Airlines
Deal found 1/20$135
This American Airlines deal was found by Cheapflights users on 1/18. 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.
Thu 3/56:52 am
BOS
-
ORD
Nonstop3h 11m
American Airlines
Thu 3/126:26 am
ORD
-
BOS
Nonstop2h 28m
American Airlines
Deal found 1/18$136
This Delta deal was found by Cheapflights users on 1/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/75:15 pm
BOS
-
ORD
Nonstop3h 11m
Delta
Sun 2/87:05 am
ORD
-
BOS
Nonstop2h 35m
Delta
Deal found 1/20$137
This Rumbo deal was found by Cheapflights users on 1/19. 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 Rumbo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/710:15 am
BOS
-
ORD
1 stop10h 16m
JetBlue
Sun 2/87:40 am
ORD
-
BOS
Nonstop2h 25m
JetBlue
Deal found 1/19$140
This Kiwi.com deal was found by Cheapflights users on 1/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/175:50 pm
BOS
-
ORD
1 stop16h 49m
Multiple Airlines
Wed 2/2511:51 am
ORD
-
BOS
1 stop12h 22m
Multiple Airlines
Deal found 1/19$141
This United Airlines deal was found by Cheapflights users on 1/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/267:45 am
BOS
-
ORD
Nonstop3h 05m
United Airlines
Sun 3/17:10 am
ORD
-
BOS
1 stop4h 43m
United Airlines
Deal found 1/20$142
This Kiwi.com deal was found by Cheapflights users on 1/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/185:50 pm
BOS
-
ORD
1 stop16h 49m
Multiple Airlines
Wed 2/2511:51 am
ORD
-
BOS
1 stop12h 22m
Multiple Airlines
Deal found 1/19$143
This Frontier deal was found by Cheapflights users on 1/20. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/911:26 am
BOS
-
MKE
1 stop7h 51m
Frontier
Mon 4/134:26 pm
MKE
-
BOS
1 stop8h 00m
Frontier
Deal found 1/20$181
This Frontier deal was found by Cheapflights users on 1/19. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/276:00 am
BOS
-
MKE
1 stop12h 25m
Frontier
Mon 3/25:30 pm
MKE
-
BOS
1 stop6h 43m
Frontier
Deal found 1/19$195

Find flight deals from Maine to Wisconsin

Keep the following information in mind while searching for Maine to Wisconsin flight deals. Data was last updated January 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$132
(JetBlue)

One-way from

$68
(United Airlines)

Popular in

September

Cheapest in

November

Average price

$391
Provider with most accurate pricing for Portland-Milwaukee-Mitchell flight deals.
Search Deals
Provider most trusted by Cheapflights users for Portland-Milwaukee-Mitchell flights.
Search Deals
From Maine to Wisconsin
Search Deals
One-way flight from Maine to Wisconsin
Search Deals
Highest demand for flights based on searches. 22% potential increase in price ($139 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($26 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Maine to Wisconsin 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 21, 2026.
Use the filters below to find and compare flights from Maine to Wisconsin that are best for you.

Fly from

Maine

Fly to

Wisconsin

Route

Depart

Return

Price

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 5/16

7:35 pm-9:36 pm

Nonstop3h 01m

Chicago O'Hare Intl

Tue 5/19

6:00 am-9:15 am

Nonstop2h 15m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 2/6

8:25 pm-10:29 pm

Nonstop3h 04m

Chicago O'Hare Intl

Sun 2/8

7:05 am-10:40 am

Nonstop2h 35m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 2/26

7:00 am-9:10 am

Nonstop3h 10m

Chicago O'Hare Intl

Mon 3/2

12:41 pm-7:58 pm

1 stop6h 17m

$140

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 2/5

9:30 am-2:25 pm

1 stop5h 55m

Chicago O'Hare Intl

Sun 2/8

7:30 am-10:52 am

Nonstop2h 22m

$152

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 2/11

2:50 pm-4:55 pm

Nonstop3h 05m

Chicago O'Hare Intl

Thu 2/12

6:04 am-2:24 pm

1 stop7h 20m

$152

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 3/5

7:00 am-9:10 am

Nonstop3h 10m

Chicago O'Hare Intl

Fri 3/6

6:04 am-2:35 pm

1 stop7h 31m

$152

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 5/16

7:00 am-8:58 am

Nonstop2h 58m

Chicago O'Hare Intl

Tue 5/19

7:00 am-10:28 am

Nonstop2h 28m

$156

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 2/19

7:15 am-9:28 am

Nonstop3h 13m

Chicago O'Hare Intl

Fri 2/27

7:05 am-10:37 am

Nonstop2h 32m

$157

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 3/10

4:25 pm-6:31 pm

Nonstop3h 06m

Chicago O'Hare Intl

Wed 3/18

10:40 am-2:04 pm

Nonstop2h 24m

$161

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 6/13

8:10 pm-10:06 pm

Nonstop2h 56m

Chicago O'Hare Intl

Tue 6/23

7:00 am-10:28 am

Nonstop2h 28m

$161

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/20

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

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

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

Currently, March is the cheapest month in which you can book a flight from Maine to Wisconsin (average of $180). Flying from Maine to Wisconsin in January is currently the most expensive (average of $288). 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 Wisconsin

Get insights into the airlines that provide service to Wisconsin. 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 Wisconsin. Reviews last updated January 21, 2026.
Get a feel of what it's like to fly with Southwest, Delta, and United Airlines from Maine to Wisconsin by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,266 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Entertainment

7.5

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,266 reviews
Southwest
8.0
Very good
4,266 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Entertainment

7.5

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Delta
7.9
Good
8,089 reviews
Southwest
8.0
Very good
4,266 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Entertainment

7.5

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
United Airlines
7.4
Good
9,191 reviews
Southwest
8.0
Very good
4,266 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Entertainment

7.5

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,174 reviews
Southwest
8.0
Very good
4,266 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Entertainment

7.5

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Related info for your journey

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

    A quick flight from Maine to Wisconsin can take about 3h 01m. JetBlue provides one of the quickest options available for as low as $137. There are 864 mi between Maine and Wisconsin. Generally, flights for this route are nonstop.

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

    The cheapest airlines for a one-way flight from Maine to Wisconsin are Delta ($128), United Airlines ($134), and American Airlines ($135).

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

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

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

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

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

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

    Currently, March is the cheapest month in which you can book a flight from Maine to Wisconsin (average of $180). Flying from Maine to Wisconsin in January is currently the most expensive (average of $288). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Maine to Wisconsin

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

Discover the top 4 airlines that operate flights from Maine to Wisconsin. 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 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$244Average$489FlexibilityNo cancel feeOn-time69%
DeltaCheapest$258Average$373FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$258Average$490FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$311Average$396FlexibilityNo cancel feeOn-time63%

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