Boston

$59+ Cheap flights from Wisconsin to Boston (BOS)

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 6/17. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — BOS
May 6 — May 131
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Cheap flight deals from Wisconsin to Boston

Keep the following information in mind while searching for Wisconsin to Boston flight deals. Data was last updated May 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$116
(Cheapflightsfares)

One-way from

$59
(JetBlue)

Popular in

March

Cheapest in

September

Average price

$296

Good round-trip deal

$208 or less

Good one-way deal

$123 or less
Provider with most accurate pricing for Milwaukee-Mitchell-Boston Logan Intl flight deals.
Provider most trusted by Cheapflights users for Milwaukee-Mitchell-Boston Logan Intl flights.
From Wisconsin to Boston Logan Intl
One-way flight from Wisconsin to Boston Logan Intl
Highest demand for flights based on searches. 4% potential increase in price ($15 potential increase over avg. RT price).
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Average for round-trip flights in May 2025
Price to beat on a round-trip flight from Wisconsin to Boston Logan Intl.
Price to beat on a one-way flight from Wisconsin to Boston Logan Intl.

Find flight deals from Wisconsin to Boston

Cheapest flights from Wisconsin to Boston
Explore the most affordable flight options available from Wisconsin to Boston. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 1, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 4/30. 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.
Thu 10/1610:48 amORD - BOS
Nonstop2h 26mSpirit Airlines
Tue 10/216:10 amBOS - ORD
1 stop12h 27mSpirit Airlines
Deal found 4/30$113
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/710:50 amORD - BOS
Nonstop2h 28mJetBlue
Sun 5/116:00 amBOS - ORD
Nonstop3h 00mJetBlue
Deal found 4/29$117
This American Airlines deal was found by Cheapflights users on 4/30. 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 6/48:20 pmORD - BOS
Nonstop2h 24mAmerican Airlines
Wed 6/115:00 amBOS - ORD
Nonstop2h 54mAmerican Airlines
Deal found 4/30$118
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/37:53 pmORD - BOS
Nonstop2h 27mUnited Airlines
Tue 8/126:59 pmBOS - ORD
1 stop5h 38mUnited Airlines
Deal found 4/29$123
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/87:00 amORD - BOS
Nonstop2h 25mDelta
Tue 5/137:15 amBOS - ORD
Nonstop2h 54mDelta
Deal found 4/29$137
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/281:50 pmORD - BOS
1 stop4h 20mSouthwest
Fri 5/305:00 amBOS - ORD
1 stop8h 45mSouthwest
Deal found 4/29$142
This Mytrip deal was found by Cheapflights users on 4/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/174:15 pmORD - BOS
1 stop7h 29mMultiple Airlines
Wed 5/213:49 pmBOS - ORD
1 stop8h 15mMultiple Airlines
Deal found 4/30$166
This JetBlue deal was found by Cheapflights users on 4/30. 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.
Fri 5/304:43 pmMKE - BOS
Nonstop2h 16mJetBlue
Tue 6/32:08 pmBOS - MKE
Nonstop2h 40mJetBlue
Deal found 4/30$187
This American Airlines deal was found by Cheapflights users on 4/30. 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 5/217:07 amMKE - BOS
1 stop5h 46mAmerican Airlines
Sat 5/316:36 pmBOS - MKE
1 stop6h 22mAmerican Airlines
Deal found 4/30$197
This Booking.com deal was found by Cheapflights users on 4/30. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/309:15 amMKE - BOS
1 stop12h 36mSpirit Airlines
Tue 6/35:45 amBOS - MKE
1 stop6h 42mSpirit Airlines
Deal found 4/30$202
This Delta deal was found by Cheapflights users on 4/30. 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 8/127:35 pmMKE - BOS
Nonstop2h 27mDelta
Tue 8/199:00 amBOS - MKE
Nonstop2h 44mDelta
Deal found 4/30$207
This eDestinos deal was found by Cheapflights users on 4/30. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/28:34 amMSP - BOS
1 stop23h 40mMultiple Airlines
Tue 6/1011:38 amBOS - MSP
Nonstop3h 10mMultiple Airlines
Deal found 4/30$208

Cheapflights Fare Finder

Customize your flight search to find flights from Wisconsin to Boston 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 May 1, 2025.
Use the filters below to find and compare flights from Wisconsin to Boston that are best for you.

Fly from

Wisconsin

Fly to

Boston

Route

Depart

Return

Price

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 10/16

10:48 am-2:14 pm

Nonstop2h 26m

Boston Logan Intl

Tue 10/21

6:10 am-5:37 pm

1 stop12h 27m

$113

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 5/10

4:20 pm-7:48 pm

Nonstop2h 28m

Boston Logan Intl

Tue 5/13

12:15 pm-2:12 pm

Nonstop2h 57m

$117

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 6/4

8:20 pm-11:44 pm

Nonstop2h 24m

Boston Logan Intl

Wed 6/11

5:00 am-6:54 am

Nonstop2h 54m

$118

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 5/31

7:00 am-10:25 am

Nonstop2h 25m

Boston Logan Intl

Mon 6/9

7:20 am-9:18 am

Nonstop2h 58m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 5/21

4:03 pm-12:17 am

1 stop7h 14m

Boston Logan Intl

Sun 5/25

6:00 am-8:00 am

Nonstop3h 00m

$140

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 5/28

1:50 pm-7:10 pm

1 stop4h 20m

Boston Logan Intl

Fri 5/30

5:00 am-12:45 pm

1 stop8h 45m

$142

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 5/17

4:15 pm-12:44 am

1 stop7h 29m

Boston Logan Intl

Wed 5/21

3:49 pm-11:04 pm

1 stop8h 15m

$166

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Fri 5/30

4:43 pm-7:59 pm

Nonstop2h 16m

Boston Logan Intl

Tue 6/3

2:08 pm-3:48 pm

Nonstop2h 40m

$187

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Wed 5/21

7:07 am-3:29 pm

1 stop7h 22m

Boston Logan Intl

Wed 8/13

6:19 pm-10:59 pm

1 stop5h 40m

$197

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Fri 5/30

9:15 am-10:51 pm

1 stop12h 36m

Boston Logan Intl

Tue 6/3

5:45 am-11:27 am

1 stop6h 42m

$202

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

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

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

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

Currently, January is the cheapest month in which you can book a flight from Wisconsin to Boston (average of $218). Flying from Wisconsin to Boston in July is currently the most expensive (average of $310). 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 WI to BOS?

Find hourly flight availability from Wisconsin to Boston. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 1, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Wisconsin to Boston as you normally would.

Rainfall in Boston by month

Plan your trip to Boston by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Boston ranges from 3.1 - 4.0 inches per month. March is typically the wettest month, when rainfall can reach 4.0 in. July is typically the driest time to visit Boston when rainfall is around 3.1 in.

Temperature in Boston by month

Plan your trip to Boston by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Boston, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 30.2 F).

Reviews of airlines servicing Boston

Get insights into the airlines that provide service to Boston. 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 Boston. Reviews last updated May 1, 2025.
See what other customers who have flown with Alaska Airlines, Southwest and Delta from Wisconsin to Boston have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.1

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.1

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.1

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
8.0
Very good

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.1

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.1

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.1

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

Related info for your journey

Find useful and relevant information for your journey from Wisconsin to Boston. 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 into for flights to Boston from Wisconsin?

    Located just 2.6 mi from the city center, Boston Logan Intl (BOS) is the airport most travelers will use when flying to Boston from Wisconsin.

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

    The cheapest airline one-way is JetBlue, with whom users have recently found tickets for as low as $59. However, be on the lookout for offers from Spirit Airlines and Southwest, as they are both options that can get you from Wisconsin to Boston for a low price.

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

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

    No one likes to see their flight delayed. When booking a flight from Wisconsin to Boston consider choosing Delta (89%), Republic Airways (89%) or KLM (87%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Wisconsin to Boston?

    On average you can expect to pay $441 for a flight from Wisconsin to Boston. The cheapest flight overall is $88 while the most popular route, (Chicago O'Hare Intl - Boston Logan Intl) is currently priced at $115.

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

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

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

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

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

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

    Currently, January is the cheapest month in which you can book a flight from Wisconsin to Boston (average of $218). Flying from Wisconsin to Boston in July is currently the most expensive (average of $310). 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

Traveling to a place near Wisconsin?

Book flights to Wisconsin if you plan to visit one of these locations
Marlborough
Warwick
Cambridge
Waltham
Framingham
Chestnut Hill
Randolph
Brockton
Lowell
Woburn
Somerville
York Beach
Saco
Burlington
West Yarmouth
Smithfield
Lincoln
Salem
Chelsea
Seabrook

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Alternative routes for Wisconsin to Boston

See prices for flight routes from nearby airports that may be better suited for you.

Top 6 airlines flying from Wisconsin to Boston

Discover the top 6 airlines that operate flights from Wisconsin to Boston. 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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$34Average$258FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$152Average$292FlexibilityNo cancel feeOn-time62%
DeltaCheapest$163Average$440FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$176Average$431FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$176Average$446FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$211Average$364FlexibilityNo cancel feeOn-time63%

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