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$70+ Cheap flights from Boston (BOS) 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 5/20. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MKE
May 23 — May 301
Sat 5/23
Sat 5/30
1 adult, Economy
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Cheap flight deals from Boston to Wisconsin

Cheapest flights from Boston to Wisconsin
Explore the most affordable flight options available from Boston to Wisconsin. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 23, 2026.

This Frontier deal was found by Cheapflights users on 4/20. 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.
Mon 5/116:00 am
BOS
-
MKE
1 stop6h 14m
Frontier
Wed 5/2012:09 pm
MKE
-
BOS
1 stop12h 15m
Frontier
Deal found 4/20$140
This Delta deal was found by Cheapflights users on 4/20. 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.
Thu 5/287:35 am
BOS
-
ORD
Nonstop2h 52m
Delta
Fri 5/297:16 pm
ORD
-
BOS
Nonstop2h 34m
Delta
Deal found 4/20$150
This American Airlines deal was found by Cheapflights users on 4/20. 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 5/164:32 pm
BOS
-
ORD
Nonstop3h 17m
American Airlines
Tue 5/196:00 am
ORD
-
BOS
Nonstop2h 27m
American Airlines
Deal found 4/20$151
This Cheapflightsfares deal was found by Cheapflights users on 4/20. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/246:00 am
BOS
-
ORD
Nonstop3h 00m
JetBlue
Wed 5/278:30 pm
ORD
-
BOS
Nonstop2h 29m
JetBlue
Deal found 4/20$152
This Cheapflightsfares deal was found by Cheapflights users on 4/20. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/117:02 am
BOS
-
ORD
Nonstop2h 57m
JetBlue
Thu 5/147:20 am
ORD
-
BOS
Nonstop2h 26m
JetBlue
Deal found 4/20$153
This JetBlue deal was found by Cheapflights users on 4/22. 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 5/3011:00 am
BOS
-
ORD
Nonstop3h 01m
JetBlue
Mon 6/18:30 pm
ORD
-
BOS
Nonstop2h 29m
JetBlue
Deal found 4/22$154
This SmartFares deal was found by Cheapflights users on 4/20. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/286:00 am
BOS
-
ORD
Nonstop3h 00m
JetBlue
Sun 5/318:30 pm
ORD
-
BOS
Nonstop2h 29m
JetBlue
Deal found 4/20$155
This United Airlines deal was found by Cheapflights users on 4/21. 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.
Wed 6/107:19 am
BOS
-
ORD
Nonstop2h 58m
United Airlines
Sat 6/137:40 pm
ORD
-
BOS
Nonstop2h 36m
United Airlines
Deal found 4/21$156
This Delta deal was found by Cheapflights users on 4/20. 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 5/309:00 am
BOS
-
ORD
1 stop5h 21m
Delta
Tue 6/25:19 pm
ORD
-
BOS
1 stop5h 10m
Delta
Deal found 4/20$157
This Delta deal was found by Cheapflights users on 4/20. 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 5/306:00 am
BOS
-
ORD
1 stop7h 16m
Delta
Mon 6/15:19 pm
ORD
-
BOS
1 stop5h 10m
Delta
Deal found 4/20$158
This Priceline deal was found by Cheapflights users on 4/20. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1612:01 pm
BOS
-
ORD
1 stop8h 50m
Multiple Airlines
Sun 5/248:50 am
ORD
-
BOS
Nonstop2h 30m
Multiple Airlines
Deal found 4/20$159
This Frontier deal was found by Cheapflights users on 4/22. 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.
Mon 5/186:00 am
BOS
-
MKE
1 stop6h 14m
Frontier
Wed 5/2012:09 pm
MKE
-
BOS
1 stop12h 15m
Frontier
Deal found 4/22$160

Find flight deals from Boston to Wisconsin

Keep the following information in mind while searching for Boston to Wisconsin flight deals. Data was last updated April 23, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$140
(Frontier)

One-way from

$70
(Expedia)

Popular in

November

Cheapest in

September

Average price

$439

Good round-trip deal

$158 or less

Good one-way deal

$128 or less
Provider with most accurate pricing for Boston Logan Intl-Milwaukee-Mitchell flight deals.
Search Deals
Provider most trusted by Cheapflights users for Boston Logan Intl-Milwaukee-Mitchell flights.
Search Deals
From Boston Logan Intl to Wisconsin
Search Deals
One-way flight from Boston Logan Intl to Wisconsin
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($49 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
Search Deals
Price to beat on a round-trip flight from Boston Logan Intl to Wisconsin.
Search Deals
Price to beat on a one-way flight from Boston Logan Intl to Wisconsin.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Boston 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 23, 2026.
Use the filters below to find and compare flights from Boston 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 6/9

8:45 pm-10:42 pm

Nonstop2h 57m

Chicago O'Hare Intl

Sat 6/13

4:30 pm-8:11 pm

Nonstop2h 41m

$157

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 5/30

9:00 am-1:21 pm

1 stop5h 21m

Chicago O'Hare Intl

Mon 6/1

5:19 pm-11:29 pm

1 stop5h 10m

$158

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 5/28

5:51 am-11:47 am

1 stop6h 56m

Chicago O'Hare Intl

Tue 6/2

7:05 am-2:15 pm

1 stop6h 10m

$158

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 7/7

8:10 am-10:06 am

Nonstop2h 56m

Chicago O'Hare Intl

Tue 7/7

8:20 pm-11:51 pm

Nonstop2h 31m

$167

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sun 5/10

7:35 am-9:27 am

Nonstop2h 52m

Chicago O'Hare Intl

Wed 5/27

9:36 am-4:28 pm

1 stop5h 52m

$177

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 6/9

5:45 am-9:36 am

1 stop4h 51m

Chicago O'Hare Intl

Thu 6/11

9:26 pm-12:59 am

Nonstop2h 33m

$182
Quickest round-trip

BostonMilwaukee

BOS - MKE

BOSMKE

Boston Logan Intl

Mon 5/11

2:25 pm-4:03 pm

Nonstop2h 38m

Milwaukee-Mitchell

Tue 5/12

4:58 pm-8:13 pm

Nonstop2h 15m

$187

BostonMilwaukee

BOS - MKE

BOSMKE

Boston Logan Intl

Sat 5/16

11:35 am-1:16 pm

Nonstop2h 41m

Milwaukee-Mitchell

Mon 5/18

7:50 pm-11:13 pm

Nonstop2h 23m

$187

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 6/9

7:27 pm-11:26 pm

1 stop4h 59m

Chicago O'Hare Intl

Sat 6/13

3:55 pm-7:30 pm

Nonstop2h 35m

$204

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 9/10

8:10 am-10:08 am

Nonstop2h 58m

Chicago O'Hare Intl

Sun 9/13

6:00 am-9:23 am

Nonstop2h 23m

$205

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/21

Showing 1-10 of 60 resultsSorted by cheapest first
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6

Best time to book a flight from Boston to Wisconsin

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

How far ahead should I book a flight from Boston to Wisconsin?

The price you pay for your flight from Boston to Wisconsin may vary depending on when you book. For the best chance of a lower fare, look to book 89 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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

Currently, August is the cheapest month in which you can book a flight from Boston to Wisconsin (average of $78). Flying from Boston to Wisconsin in March is currently the most expensive (average of $207). 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.

What is the cheapest time of day to fly from BOS to WI?

Find hourly flight availability from Boston to Wisconsin. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 23, 2026.

It’s optimal to fly from Boston to Wisconsin in the evening. By choosing this option you can save up to 37% on the cost of your flight, compared to a flight in the morning.

What is the cheapest day to fly from Boston to Wisconsin?

Use this chart to determine the cheapest time to fly round-trip from Boston to Wisconsin. Price data was last updated on April 18, 2026.

Travelers seeking maximum savings on their Boston to Wisconsin flight should consider departing on Wednesday at noon when fares are most often at their lowest. Monday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

How much does it cost to fly round-trip from Boston 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 23, 2026.
Read through reviews of airlines operating flights from Boston to Wisconsin, such as Southwest,Delta, andUnited Airlines. 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
4,327 reviews

Crew

8.6

Overall

8.0

Boarding

8.1

Food

7.0

Comfort

8.0

Entertainment

7.5

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
4,327 reviews
Southwest
8.0
Very good
4,327 reviews

Crew

8.6

Overall

8.0

Boarding

8.1

Food

7.0

Comfort

8.0

Entertainment

7.5

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
8,438 reviews
Southwest
8.0
Very good
4,327 reviews

Crew

8.6

Overall

8.0

Boarding

8.1

Food

7.0

Comfort

8.0

Entertainment

7.5

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
9,635 reviews
Southwest
8.0
Very good
4,327 reviews

Crew

8.6

Overall

8.0

Boarding

8.1

Food

7.0

Comfort

8.0

Entertainment

7.5

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.
JetBlue
7.2
Good
2,952 reviews
Southwest
8.0
Very good
4,327 reviews

Crew

8.6

Overall

8.0

Boarding

8.1

Food

7.0

Comfort

8.0

Entertainment

7.5

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
11,659 reviews
Southwest
8.0
Very good
4,327 reviews

Crew

8.6

Overall

8.0

Boarding

8.1

Food

7.0

Comfort

8.0

Entertainment

7.5

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 Boston to Wisconsin. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Boston to Wisconsin?

    For a flight from Boston to Wisconsin, you will be flying from Logan Intl. Boston Logan Intl (BOS) is just 2.6 mi from the center of the city.

  • How popular is this Boston to Wisconsin flight route?

    This flight path from Boston Logan Intl to Wisconsin was viewed by 1 users in the past month. Keep an eye out for changes in search interest prior to high and low season.

  • How long is the flight from Boston to Wisconsin?

    There are many flights that can get you from Boston to Wisconsin in 2h 56m. Fly via Delta, JetBlue, or Southwest to get the fastest option. Airlines will cover a distance of 864 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    $88 is the cheapest one-way deal found within the past few days, from American Airlines. You may also be able to find cheap deals on JetBlue and Southwest, with prices starting from $88 and $98, respectively.

  • What are the most popular routes from Boston to Wisconsin?

    While some choose either Boston Logan Intl - Minneapolis St Paul or Boston Logan Intl - Milwaukee-Mitchell, Boston Logan Intl - Chicago O'Hare Intl is the most popular route from Boston to Wisconsin.

  • What are the most reliable airlines from Boston to Wisconsin?

    The top 3 most reliable airlines when flying from Boston to Wisconsin are EL AL (91%), Delta (88%) and Republic Airways (88%).

  • What are the cheapest flights from Boston to Wisconsin?

    Looking for the cheapest flight from Boston to Wisconsin? While on average our users pay $238, our data indicates the cheapest price to be $68. The most popular route (Boston Logan Intl - Chicago O'Hare Intl), is priced around $132.

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

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

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

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

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

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

    Currently, August is the cheapest month in which you can book a flight from Boston to Wisconsin (average of $78). Flying from Boston to Wisconsin in March is currently the most expensive (average of $207). 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 Boston to Wisconsin

See prices for flight routes from nearby airports that may be better suited for you.
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Top 5 airlines flying from Boston to Wisconsin

Discover the top 5 airlines that operate flights from Boston 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 23, 2026.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$99Average$270FlexibilityNo cancel feeOn-time62%
DeltaCheapest$141Average$418FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$176Average$271FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$176Average$455FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$196Average$440FlexibilityNo cancel feeOn-time71%

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