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Maine

$58+ 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 4/30. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — PWM
Apr 26 — May 31
Sun 4/26
Sun 5/3
1 adult, Economy
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Cheap 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 March 27, 2026.

This Delta deal was found by Cheapflights users on 3/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/226:00 am
ORD
-
BOS
Nonstop2h 26m
Delta
Wed 4/294:55 pm
BOS
-
ORD
Nonstop3h 04m
Delta
Deal found 3/26$135
This SmartFares deal was found by Cheapflights users on 3/27. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/108:58 am
ORD
-
BOS
Nonstop2h 30m
JetBlue
Sun 4/126:05 am
BOS
-
ORD
Nonstop3h 03m
JetBlue
Deal found 3/27$137
This Priceline deal was found by Cheapflights users on 3/24. 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.
Tue 4/216:08 pm
ORD
-
BOS
1 stop6h 23m
Multiple Airlines
Tue 4/287:35 pm
BOS
-
ORD
Nonstop3h 04m
Multiple Airlines
Deal found 3/24$138
This Expedia deal was found by Cheapflights users on 3/24. 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.
Tue 4/216:08 pm
ORD
-
BOS
1 stop6h 23m
Frontier
Mon 4/2712:31 pm
BOS
-
ORD
1 stop11h 30m
Frontier
Deal found 3/24$140
This SmartFares deal was found by Cheapflights users on 3/24. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/309:49 am
ORD
-
BOS
Nonstop2h 26m
JetBlue
Mon 5/47:35 pm
BOS
-
ORD
Nonstop3h 01m
JetBlue
Deal found 3/24$141
This Expedia deal was found by Cheapflights users on 3/24. 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.
Tue 4/219:41 am
ORD
-
BOS
Nonstop2h 26m
Multiple Airlines
Mon 4/2712:31 pm
BOS
-
ORD
1 stop11h 30m
Multiple Airlines
Deal found 3/24$143
This Super.com deal was found by Cheapflights users on 3/26. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/299:41 am
ORD
-
BOS
Nonstop2h 28m
JetBlue
Sun 5/37:02 am
BOS
-
ORD
Nonstop2h 57m
JetBlue
Deal found 3/26$144
This United Airlines deal was found by Cheapflights users on 3/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/2111:17 am
ORD
-
BOS
Nonstop2h 31m
United Airlines
Thu 4/239:20 am
BOS
-
ORD
Nonstop3h 00m
United Airlines
Deal found 3/26$145
This United Airlines deal was found by Cheapflights users on 3/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/106:00 am
ORD
-
BOS
Nonstop2h 25m
United Airlines
Tue 4/1411:00 am
BOS
-
ORD
Nonstop2h 59m
United Airlines
Deal found 3/26$147
This JetBlue deal was found by Cheapflights users on 3/24. 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.
Sat 5/231:56 pm
ORD
-
BOS
Nonstop2h 31m
JetBlue
Tue 5/266:00 am
BOS
-
ORD
Nonstop3h 00m
JetBlue
Deal found 3/24$148
This Expedia deal was found by Cheapflights users on 3/25. 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.
Tue 4/216:08 pm
ORD
-
BOS
1 stop6h 23m
Multiple Airlines
Thu 4/237:00 am
BOS
-
ORD
Nonstop3h 00m
Multiple Airlines
Deal found 3/25$149
This American Airlines deal was found by Cheapflights users on 3/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/95:06 am
MKE
-
BOS
1 stop4h 33m
American Airlines
Mon 4/135:40 pm
BOS
-
MKE
1 stop6h 17m
American Airlines
Deal found 3/26$159

Find flight deals from Wisconsin to Maine

Keep the following information in mind while searching for Wisconsin to Maine flight deals. Data was last updated March 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$135
(Delta)

One-way from

$58
(Super.com)

Popular in

December

Cheapest in

April

Average price

$416
Provider with most accurate pricing for Milwaukee-Mitchell-Portland flight deals.
Search Deals
Provider most trusted by Cheapflights users for Milwaukee-Mitchell-Portland flights.
Search Deals
From Wisconsin to Maine
Search Deals
One-way flight from Wisconsin to Maine
Search Deals
Highest demand for flights based on searches. 16% potential increase in price ($76 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($24 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
Search Deals

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 March 27, 2026.
Use the filters below to find and compare flights from Wisconsin to Maine that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 4/28

10:15 am-1:35 pm

Nonstop2h 20m

Boston Logan Intl

Wed 4/29

4:00 pm-11:59 pm

1 stop8h 59m

$146

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 4/16

7:30 am-11:01 am

Nonstop2h 31m

Boston Logan Intl

Thu 4/23

9:20 am-11:20 am

Nonstop3h 00m

$157

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 4/22

7:14 am-3:23 pm

1 stop7h 09m

Boston Logan Intl

Wed 4/29

3:10 pm-9:38 pm

1 stop7h 28m

$157

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 5/12

7:30 am-11:01 am

Nonstop2h 31m

Boston Logan Intl

Fri 5/15

7:26 pm-11:37 pm

1 stop5h 11m

$166

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 4/30

10:15 am-1:35 pm

Nonstop2h 20m

Boston Logan Intl

Mon 5/4

6:00 pm-10:15 pm

1 stop5h 15m

$169

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 5/12

2:40 pm-10:30 pm

1 stop6h 50m

Boston Logan Intl

Fri 5/15

5:30 am-4:05 pm

2 stops11h 35m

$171

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 4/30

2:40 pm-11:15 pm

1 stop7h 35m

Boston Logan Intl

Mon 5/4

8:25 am-12:50 pm

1 stop5h 25m

$175

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 6/10

8:30 pm-11:59 pm

Nonstop2h 29m

Boston Logan Intl

Sun 6/14

8:00 am-9:56 am

Nonstop2h 56m

$176

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 4/18

9:30 pm-12:59 am

Nonstop2h 29m

Boston Logan Intl

Sat 4/25

5:45 am-9:38 am

1 stop4h 53m

$176

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 6/3

6:00 am-11:16 am

1 stop4h 16m

Boston Logan Intl

Tue 6/9

6:00 am-7:58 am

Nonstop2h 58m

$177

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/25

Showing 1-10 of 60 resultsSorted by cheapest first
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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, April is the cheapest month in which you can book a flight from Wisconsin to Maine (average of $210). Flying from Wisconsin to Maine in January 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 Wisconsin to Maine?

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 March 27, 2026.
Peruse reviews from past customers who have flown with Southwest,Delta, andUnited 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
4,331 reviews

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Crew

8.6

Food

7.0

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
4,331 reviews
Southwest
8.0
Very good
4,331 reviews

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Crew

8.6

Food

7.0

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
8,341 reviews
Southwest
8.0
Very good
4,331 reviews

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Crew

8.6

Food

7.0

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
9,491 reviews
Southwest
8.0
Very good
4,331 reviews

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Crew

8.6

Food

7.0

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
11,504 reviews
Southwest
8.0
Very good
4,331 reviews

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Crew

8.6

Food

7.0

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 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 Delta, United Airlines, and Southwest fly from Wisconsin to Maine in about 2h 20m. The time it takes to get you to your destination can typically vary by up to 4h 35m. The distance from Wisconsin to Maine is about 864 mi. This flight may include one or multiple stops.

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

    For one-way options, check prices for American Airlines. According to our data, you can fly for as low as $86. Users have also found prices from $118 and $124 on Southwest and Delta, 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, April is the cheapest month in which you can book a flight from Wisconsin to Maine (average of $210). Flying from Wisconsin to Maine in January 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 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 March 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$210Average$447FlexibilityNo cancel feeOn-time71%
DeltaCheapest$236Average$410FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$258Average$422FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$266Average$394FlexibilityNo cancel feeOn-time63%

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