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$68+ 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 8/5. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — BOS
Jul 6 — Jul 131
Sun 7/6
Sun 7/13
1 adult, Economy
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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 July 1, 2025.

Round-trip from

$132
(Priceline)

One-way from

$68
(FlightHub)

Popular in

December

Cheapest in

May

Average price

$276

Good round-trip deal

$151 or less

Good one-way deal

$108 or less
From Wisconsin to Boston Logan Intl
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One-way flight from Wisconsin to Boston Logan Intl
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Highest demand for flights based on searches. 12% potential increase in price ($46 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Price to beat on a round-trip flight from Wisconsin to Boston Logan Intl.
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Price to beat on a one-way flight from Wisconsin to Boston Logan Intl.
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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 July 1, 2025.

This Priceline deal was found by Cheapflights users on 6/29. 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.
Tue 9/911:45 amORD - BOS
1 stop11h 10mMultiple Airlines
Sat 9/138:38 amBOS - ORD
1 stop9h 11mMultiple Airlines
Deal found 6/29$132
This Priceline deal was found by Cheapflights users on 6/29. 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.
Sat 8/212:20 pmORD - BOS
1 stop11h 19mFrontier
Thu 8/76:00 amBOS - ORD
1 stop8h 56mFrontier
Deal found 6/29$135
This JetBlue deal was found by Cheapflights users on 6/30. 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 7/118:40 amORD - BOS
Nonstop2h 24mJetBlue
Wed 7/166:00 amBOS - ORD
Nonstop2h 55mJetBlue
Deal found 6/30$137
This American Airlines deal was found by Cheapflights users on 6/29. 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.
Thu 7/108:30 pmORD - BOS
Nonstop2h 44mAmerican Airlines
Sun 7/135:00 amBOS - ORD
Nonstop2h 58mAmerican Airlines
Deal found 6/29$139
This FlightHub deal was found by Cheapflights users on 6/29. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/155:05 amORD - BOS
1 stop13h 29mSpirit Airlines
Tue 7/228:39 pmBOS - ORD
1 stop13h 16mSpirit Airlines
Deal found 6/29$140
This United Airlines deal was found by Cheapflights users on 6/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/1511:05 amORD - BOS
Nonstop2h 37mUnited Airlines
Tue 7/157:04 pmBOS - ORD
1 stop5h 37mUnited Airlines
Deal found 6/30$143
This Delta deal was found by Cheapflights users on 6/30. 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.
Wed 7/237:00 amORD - BOS
Nonstop2h 31mDelta
Wed 7/234:05 pmBOS - ORD
Nonstop3h 06mDelta
Deal found 6/30$155
This Southwest deal was found by Cheapflights users on 6/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/222:55 pmORD - BOS
1 stop6h 40mSouthwest
Tue 8/265:40 amBOS - ORD
1 stop7h 10mSouthwest
Deal found 6/30$157
This JetBlue deal was found by Cheapflights users on 6/30. 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.
Tue 8/194:03 pmMKE - BOS
Nonstop2h 12mJetBlue
Tue 8/261:40 pmBOS - MKE
Nonstop2h 28mJetBlue
Deal found 6/30$157
This Southwest deal was found by Cheapflights users on 6/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/273:55 pmMKE - BOS
1 stop4h 35mSouthwest
Thu 10/26:10 pmBOS - MKE
1 stop5h 40mSouthwest
Deal found 6/30$177
This United Airlines deal was found by Cheapflights users on 6/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/185:31 pmMKE - BOS
1 stop6h 28mUnited Airlines
Sat 7/268:02 pmBOS - MKE
1 stop4h 52mUnited Airlines
Deal found 6/30$202
This Delta deal was found by Cheapflights users on 6/30. 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.
Fri 8/157:55 pmMKE - BOS
Nonstop2h 24mDelta
Mon 8/185:20 pmBOS - MKE
Nonstop2h 54mDelta
Deal found 6/30$207

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 July 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

Tue 9/9

11:45 am-11:55 pm

1 stop11h 10m

Boston Logan Intl

Sat 9/13

8:38 am-4:49 pm

1 stop9h 11m

$132

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 8/2

12:20 pm-12:39 am

1 stop11h 19m

Boston Logan Intl

Thu 8/7

6:00 am-1:56 pm

1 stop8h 56m

$135

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 7/11

8:40 am-12:04 pm

Nonstop2h 24m

Boston Logan Intl

Wed 7/16

6:00 am-7:55 am

Nonstop2h 55m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 7/29

5:05 am-7:34 pm

1 stop13h 29m

Boston Logan Intl

Tue 7/29

8:39 pm-8:55 am

1 stop13h 16m

$138

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 7/15

11:05 am-2:42 pm

Nonstop2h 37m

Boston Logan Intl

Tue 7/15

7:04 pm-11:41 pm

1 stop5h 37m

$143

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 8/22

2:55 pm-10:35 pm

1 stop6h 40m

Boston Logan Intl

Tue 8/26

5:40 am-11:50 am

1 stop7h 10m

$157

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Tue 8/19

4:03 pm-7:15 pm

Nonstop2h 12m

Boston Logan Intl

Tue 8/26

1:40 pm-3:08 pm

Nonstop2h 28m

$157

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 8/29

8:25 pm-11:59 pm

Nonstop2h 34m

Boston Logan Intl

Tue 9/2

8:35 am-10:30 am

Nonstop2h 55m

$165

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 8/30

2:10 pm-5:54 pm

Nonstop2h 44m

Boston Logan Intl

Sun 8/31

7:20 am-9:15 am

Nonstop2h 55m

$167

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Sat 9/27

3:55 pm-9:30 pm

1 stop4h 35m

Boston Logan Intl

Thu 10/2

6:10 pm-10:50 pm

1 stop5h 40m

$177

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/29

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 June is currently the most expensive (average of $306). 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 July 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.

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 July 1, 2025.
Peruse reviews from past customers who have flown with Alaska Airlines, Southwest, and Delta from Wisconsin to Boston to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Comfort

7.8

Crew

8.5

Overall

8.0

Boarding

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Comfort

7.8

Crew

8.5

Overall

8.0

Boarding

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,273 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Comfort

7.8

Crew

8.5

Overall

8.0

Boarding

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,973 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Comfort

7.8

Crew

8.5

Overall

8.0

Boarding

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,858 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Comfort

7.8

Crew

8.5

Overall

8.0

Boarding

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
JetBlue
7.3
Good
2,919 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Comfort

7.8

Crew

8.5

Overall

8.0

Boarding

8.1

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 Spirit Airlines, with whom users have recently found tickets for as low as $68. However, be on the lookout for offers from JetBlue and American Airlines, 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?

    Most travelers choose Chicago O'Hare Intl - Boston Logan Intl, Minneapolis St Paul - Boston Logan Intl or Milwaukee-Mitchell - Boston Logan Intl when deciding on the best route 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 JetBlue (78%), WestJet (75%) or Scandinavian Airlines (74%) 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 $222 for a flight from Wisconsin to Boston. The cheapest flight overall is $78 while the most popular route, (Chicago O'Hare Intl - Boston Logan Intl) is currently priced at $125.

  • 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 June is currently the most expensive (average of $306). 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
Cambridge
Medford
Watertown
Warwick
Seabrook
Waltham
Framingham
Cranston
Randolph
Chestnut Hill
Chelsea
Brockton
York Beach
Saco
Burlington
West Yarmouth
Smithfield
Swansea
Lincoln
Quincy

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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.
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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 July 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$34Average$258FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$135Average$277FlexibilityNo cancel feeOn-time62%
DeltaCheapest$165Average$426FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$176Average$416FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$176Average$433FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$186Average$338FlexibilityNo cancel feeOn-time63%

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