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Wisconsin

$70+ 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 5/23. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MKE
May 30 — Jun 61
Sat 5/30
Sat 6/6
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 April 30, 2026.

This Travelocity deal was found by Cheapflights users on 4/26. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/1810:17 am
BOS
-
ORD
1 stop13h 56m
Multiple Airlines
Tue 5/268:30 pm
ORD
-
BOS
Nonstop2h 29m
Multiple Airlines
Deal found 4/26$159
This Expedia deal was found by Cheapflights users on 4/26. 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.
Wed 5/136:00 am
BOS
-
MKE
1 stop6h 14m
Frontier
Wed 5/2012:09 pm
MKE
-
BOS
1 stop12h 15m
Frontier
Deal found 4/26$160
This Frontier deal was found by Cheapflights users on 4/28. 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.
Wed 5/1310:07 am
BOS
-
ORD
1 stop14h 06m
Frontier
Tue 5/191:59 pm
ORD
-
BOS
1 stop10h 25m
Frontier
Deal found 4/28$160
This Cheapflightsfares deal was found by Cheapflights users on 4/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/155:20 pm
BOS
-
ORD
Nonstop3h 05m
JetBlue
Wed 7/2210:56 am
ORD
-
BOS
Nonstop2h 27m
JetBlue
Deal found 4/29$162
This CheapOair deal was found by Cheapflights users on 4/26. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/196:47 pm
BOS
-
ORD
Nonstop3h 06m
Multiple Airlines
Wed 5/201:59 pm
ORD
-
BOS
1 stop10h 25m
Multiple Airlines
Deal found 4/26$164
This Super.com deal was found by Cheapflights users on 4/29. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/78:10 am
BOS
-
ORD
Nonstop2h 56m
JetBlue
Tue 7/78:20 pm
ORD
-
BOS
Nonstop2h 31m
JetBlue
Deal found 4/29$165
This American Airlines deal was found by Cheapflights users on 4/29. 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.
Tue 6/167:46 pm
BOS
-
ORD
Nonstop3h 14m
American Airlines
Wed 6/177:00 am
ORD
-
BOS
Nonstop2h 26m
American Airlines
Deal found 4/29$166
This Delta deal was found by Cheapflights users on 4/28. 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 5/278:40 pm
BOS
-
ORD
Nonstop2h 55m
Delta
Sat 5/307:00 am
ORD
-
BOS
Nonstop2h 35m
Delta
Deal found 4/28$167
This American Airlines deal was found by Cheapflights users on 4/28. 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 5/268:37 am
BOS
-
ORD
Nonstop3h 03m
American Airlines
Tue 6/26:00 am
ORD
-
BOS
Nonstop2h 27m
American Airlines
Deal found 4/28$168
This Expedia deal was found by Cheapflights users on 4/26. 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.
Wed 5/132:25 pm
BOS
-
MKE
Nonstop2h 38m
Multiple Airlines
Wed 5/2012:09 pm
MKE
-
BOS
1 stop12h 15m
Multiple Airlines
Deal found 4/26$169
This Priceline deal was found by Cheapflights users on 4/29. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/136:47 pm
BOS
-
ORD
Nonstop3h 06m
Multiple Airlines
Wed 5/201:59 pm
ORD
-
BOS
1 stop10h 25m
Multiple Airlines
Deal found 4/29$169
This Kiwi.com deal was found by Cheapflights users on 4/26. 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 5/265:45 am
BOS
-
ORD
1 stop31h 52m
Multiple Airlines
Tue 6/21:50 pm
ORD
-
BOS
1 stop10h 34m
Multiple Airlines
Deal found 4/26$170

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 April 30, 2026.

Round-trip from

$159
(Expedia)

One-way from

$70
(Frontier)

Popular in

September

Cheapest in

November

Average price

$557
From Maine to Wisconsin
Search Deals
One-way flight from Maine to Wisconsin
Search Deals
Highest demand for flights based on searches. 18% potential increase in price ($111 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($24 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 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 April 30, 2026.
Use the filters below to find and compare flights from Maine to Wisconsin that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 7/14

5:20 pm-7:25 pm

Nonstop3h 05m

Chicago O'Hare Intl

Thu 7/16

8:20 pm-11:51 pm

Nonstop2h 31m

$172

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 8/20

7:10 am-9:09 am

Nonstop2h 59m

Chicago O'Hare Intl

Sat 8/22

7:46 pm-11:20 pm

Nonstop2h 34m

$177

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sun 5/31

6:00 am-8:00 am

Nonstop3h 00m

Chicago O'Hare Intl

Sat 6/6

1:55 pm-5:24 pm

Nonstop2h 29m

$182

BostonMilwaukee

BOS - MKE

BOSMKE

Boston Logan Intl

Tue 5/12

5:20 pm-7:08 pm

Nonstop2h 48m

Milwaukee-Mitchell

Fri 5/15

7:50 pm-11:13 pm

Nonstop2h 23m

$187

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 7/17

5:20 pm-7:25 pm

Nonstop3h 05m

Chicago O'Hare Intl

Mon 7/20

8:20 pm-11:51 pm

Nonstop2h 31m

$191

BostonMilwaukee

BOS - MKE

BOSMKE

Boston Logan Intl

Tue 5/26

9:10 am-10:53 am

Nonstop2h 43m

Milwaukee-Mitchell

Thu 5/28

6:00 am-2:15 pm

1 stop7h 15m

$197

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sun 6/7

7:30 am-9:28 am

Nonstop2h 58m

Chicago O'Hare Intl

Fri 6/12

7:25 pm-11:02 pm

Nonstop2h 37m

$201

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 9/19

7:30 am-9:28 am

Nonstop2h 58m

Chicago O'Hare Intl

Mon 9/21

7:00 am-10:28 am

Nonstop2h 28m

$205

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 5/29

8:40 pm-10:35 pm

Nonstop2h 55m

Chicago O'Hare Intl

Sat 5/30

7:00 am-10:35 am

Nonstop2h 35m

$237

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 5/29

1:29 pm-5:49 pm

1 stop5h 20m

Chicago O'Hare Intl

Wed 6/3

3:50 pm-7:27 pm

Nonstop2h 37m

$241

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/28

Showing 1-10 of 60 resultsSorted by cheapest first
1
2
3
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6

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, December is the cheapest month in which you can book a flight from Maine to Wisconsin (average of $193). Flying from Maine to Wisconsin in March is currently the most expensive (average of $329). 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.

How much does it cost to fly round-trip from Maine to Wisconsin?

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 April 30, 2026.
Get a feel of what it's like to fly with Southwest,Delta, andUnited 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
4,314 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,314 reviews
Southwest
8.0
Very good
4,314 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Delta
7.9
Good
8,463 reviews
Southwest
8.0
Very good
4,314 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
United Airlines
7.4
Good
9,677 reviews
Southwest
8.0
Very good
4,314 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
American Airlines
7.1
Good
11,681 reviews
Southwest
8.0
Very good
4,314 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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 2h 48m. JetBlue provides one of the quickest options available for as low as $187. There are 857 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 American Airlines ($115), Delta ($135), and United Airlines ($148).

  • 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, December is the cheapest month in which you can book a flight from Maine to Wisconsin (average of $193). Flying from Maine to Wisconsin in March is currently the most expensive (average of $329). 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 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 April 30, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$258Average$432FlexibilityNo cancel feeOn-time71%
DeltaCheapest$258Average$418FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$262Average$442FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$311Average$477FlexibilityNo cancel feeOn-time63%

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