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$98+ 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 8/22. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MKE
Aug 5 — Aug 121
Wed 8/5
Wed 8/12
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 July 6, 2026.

This American Airlines deal was found by Cheapflights users on 7/1. 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.
Wed 7/1512:01 pm
BOS
-
ORD
Nonstop3h 01m
American Airlines
Wed 7/226:00 am
ORD
-
BOS
Nonstop2h 34m
American Airlines
Deal found 7/1$170
This United Airlines deal was found by Cheapflights users on 7/3. 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 7/287:19 am
BOS
-
ORD
Nonstop2h 58m
United Airlines
Wed 7/296:00 am
ORD
-
BOS
1 stop4h 16m
United Airlines
Deal found 7/3$172
This United Airlines deal was found by Cheapflights users on 7/3. 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.
Sat 7/258:20 pm
BOS
-
ORD
Nonstop3h 00m
United Airlines
Sat 9/193:35 pm
ORD
-
BOS
Nonstop2h 44m
United Airlines
Deal found 7/3$173
This Flysmarter deal was found by Cheapflights users on 7/2. 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 Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/228:41 am
BOS
-
ORD
1 stop8h 36m
JetBlue
Mon 8/248:20 pm
ORD
-
BOS
Nonstop2h 31m
JetBlue
Deal found 7/2$174
This JetBlue deal was found by Cheapflights users on 7/2. 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 8/128:15 am
BOS
-
ORD
Nonstop2h 56m
JetBlue
Thu 8/209:35 am
ORD
-
BOS
1 stop6h 32m
JetBlue
Deal found 7/2$175
This Jettzy deal was found by Cheapflights users on 7/3. 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 Jettzy is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/174:55 pm
BOS
-
ORD
1 stop6h 03m
JetBlue
Mon 8/248:20 pm
ORD
-
BOS
Nonstop2h 31m
JetBlue
Deal found 7/3$177
This Delta deal was found by Cheapflights users on 7/2. 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.
Tue 7/217:30 am
BOS
-
ORD
Nonstop2h 56m
Delta
Thu 7/3010:28 am
ORD
-
BOS
Nonstop2h 31m
Delta
Deal found 7/2$178
This United Airlines deal was found by Cheapflights users on 7/2. 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.
Mon 7/207:19 am
BOS
-
ORD
Nonstop2h 58m
United Airlines
Tue 7/289:41 pm
ORD
-
BOS
Nonstop2h 33m
United Airlines
Deal found 7/2$179
This United Airlines deal was found by Cheapflights users on 7/2. 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.
Mon 7/276:00 am
BOS
-
ORD
Nonstop2h 58m
United Airlines
Wed 7/296:00 am
ORD
-
BOS
1 stop4h 16m
United Airlines
Deal found 7/2$180
This JetBlue deal was found by Cheapflights users on 7/1. 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 7/225:10 pm
BOS
-
ORD
Nonstop3h 05m
JetBlue
Sat 7/251:09 pm
ORD
-
BOS
Nonstop2h 34m
JetBlue
Deal found 7/1$182
This Cheapflightsfares deal was found by Cheapflights users on 7/2. 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 9/98:45 am
BOS
-
MKE
Nonstop2h 50m
JetBlue
Sat 9/1211:25 am
MKE
-
BOS
Nonstop2h 39m
JetBlue
Deal found 7/2$189
This Traveloka deal was found by Cheapflights users on 7/5. 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 Traveloka is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/197:10 am
BOS
-
MKE
Nonstop2h 34m
JetBlue
Wed 8/269:36 am
MKE
-
BOS
Nonstop2h 13m
JetBlue
Deal found 7/5$194

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 July 6, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$170
(United Airlines)

One-way from

$98
(United Airlines)

Popular in

November

Cheapest in

September

Average price

$274

Good round-trip deal

$193 or less

Good one-way deal

$132 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. 13% potential increase in price ($53 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 July 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 July 6, 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

Sat 7/18

6:00 am-7:58 am

Nonstop2h 58m

Chicago O'Hare Intl

Wed 7/22

7:45 pm-11:21 pm

Nonstop2h 36m

$170

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 7/18

6:43 pm-8:40 pm

Nonstop2h 57m

Chicago O'Hare Intl

Sat 7/25

6:20 pm-9:56 pm

Nonstop2h 36m

$170

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 8/20

5:45 am-9:38 am

1 stop4h 53m

Chicago O'Hare Intl

Sat 8/22

6:15 am-9:36 am

Nonstop2h 21m

$172

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 8/4

8:15 pm-10:15 pm

Nonstop3h 00m

Chicago O'Hare Intl

Tue 8/11

6:00 am-11:17 am

1 stop4h 17m

$172

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 9/1

2:40 pm-9:58 pm

1 stop8h 18m

Chicago O'Hare Intl

Sat 9/5

1:49 pm-5:59 pm

Nonstop3h 10m

$175

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 8/22

11:05 am-12:59 pm

Nonstop2h 54m

Chicago O'Hare Intl

Mon 8/24

6:00 am-2:43 pm

1 stop7h 43m

$176

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 7/21

7:19 am-9:17 am

Nonstop2h 58m

Chicago O'Hare Intl

Thu 7/30

9:41 pm-1:14 am

Nonstop2h 33m

$178

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 8/31

7:30 am-9:26 am

Nonstop2h 56m

Chicago O'Hare Intl

Sat 9/12

11:30 am-3:15 pm

Nonstop2h 45m

$181

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 8/22

5:45 am-9:38 am

1 stop4h 53m

Chicago O'Hare Intl

Sat 8/29

7:45 am-11:19 am

Nonstop2h 34m

$181

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sun 7/26

6:00 am-7:58 am

Nonstop2h 58m

Chicago O'Hare Intl

Thu 7/30

9:41 pm-1:14 am

Nonstop2h 33m

$187

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/1

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

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

Currently, April is the cheapest month in which you can book a flight from Boston to Wisconsin (average of $68). 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 July 6, 2026.

It’s optimal to fly from Boston to Wisconsin in the evening. By choosing this option you can save up to 19% on the cost of your flight, compared to a flight in the afternoon.

How much does it cost to fly round-trip 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 66 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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 July 4, 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. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

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 July 6, 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
7.9
Good
4,252 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Libby,Jun 2026

TUS - LAS

One delay in a 2 layover flight=a good trip. The crew was great.
Southwest
7.9
Good
4,252 reviews
Southwest
7.9
Good
4,252 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Libby,Jun 2026

TUS - LAS

One delay in a 2 layover flight=a good trip. The crew was great.
Delta
7.8
Good
8,452 reviews
Southwest
7.9
Good
4,252 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Libby,Jun 2026

TUS - LAS

One delay in a 2 layover flight=a good trip. The crew was great.
United Airlines
7.4
Good
9,940 reviews
Southwest
7.9
Good
4,252 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Libby,Jun 2026

TUS - LAS

One delay in a 2 layover flight=a good trip. The crew was great.
American Airlines
7.1
Good
11,782 reviews
Southwest
7.9
Good
4,252 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Libby,Jun 2026

TUS - LAS

One delay in a 2 layover flight=a good trip. The crew was great.
JetBlue
7.1
Good
3,009 reviews
Southwest
7.9
Good
4,252 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Libby,Jun 2026

TUS - LAS

One delay in a 2 layover flight=a good trip. The crew was great.

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 United Airlines, JetBlue, or Delta 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 United Airlines, 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 Republic Airways (88%), KLM (87%) and JetBlue (87%).

  • What are the cheapest flights from Boston to Wisconsin?

    Looking for the cheapest flight from Boston to Wisconsin? While on average our users pay $261, our data indicates the cheapest price to be $108. The most popular route (Boston Logan Intl - Chicago O'Hare Intl), is priced around $147.

  • 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, April is the cheapest month in which you can book a flight from Boston to Wisconsin (average of $68). 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 July 6, 2026.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$104Average$249FlexibilityNo cancel feeOn-time62%
DeltaCheapest$120Average$416FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$176Average$413FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$186Average$284FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$206Average$467FlexibilityNo cancel feeOn-time71%

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