To Boston

Cheap Flights from Milwaukee to Boston

Browse current best options from Milwaukee. Become a member to unlock all deals and get alerts when new deals appear.

Deals from

Milwaukee

RatePunk searches hundreds of travel sites at once for deals on flights to Boston

Prices updated 24 days ago

486,190 searches this week

171 airlines compared

80%+ AI score for best value

Fares are subject to change and may not be available for all dates. (Data last updated May 29, 2026.)

Today’s best flight deals from Milwaukee to Boston

Explore current cheapest deals departing from Milwaukee to Boston

Round trip

Sort by: Cheapest

August 22 - August 28

Cheapest

MKE - Boston

$317

$196

Round trip

August 22 - August 29

Cheapest

MKE - Boston

$316

$196

Round trip

September 10 - September 14

Cheapest

MKE - Boston

$293

$196

Round trip

October 17 - October 20

Cheapest

Best

MKE - Boston

$345

$196

Round trip

July 8 - July 10

MKE - Boston

$330

$197

Round trip

July 3 - July 4

MKE - Boston

$340

$197

Round trip

July 3 - July 8

MKE - Boston

$321

$197

Round trip

July 2 - July 7

Earliest

MKE - Boston

$333

$197

Round trip

August 11 - August 21

MKE - Boston

$285

$197

Round trip

August 26 - August 30

MKE - Boston

$329

$197

Round trip

Unlock all 500+ flight deals to Boston and get alerts when great deals appear

Route Intelligence — 486,190 Searches this Week

Insights for flights from Milwaukee to Boston

Right now, only 7% of recent fares for flights from Milwaukee to Boston are classified as a good price. Fares for this route typically range from $229–$529, with a median price of $284. Current fares are significantly above the typical level, suggesting that now may not be the optimal time to find cheap flights from Milwaukee to Boston. New deals appear almost daily, so monitoring prices could be beneficial.

When considering the cheapest time to fly from Milwaukee to Boston, December stands out with a median fare of $94. January also offers lower prices, with a median of $170. Travelers can also find more favorable fares in July, where the median price is $235.

A typical journey from Milwaukee to Boston takes about 8h 40m, including connections. This route is primarily served by connecting itineraries, as most itineraries connect at least once. For those flights that do involve connections, the median number of stopovers is 2.

The distance between Milwaukee and Boston is 1381 kilometers, classifying this as a short-haul route. This distance means you'll typically be in the air for a relatively brief period, though connecting flights will extend the overall travel time.

How much is a round trip from Milwaukee to Boston

Regular price: $267 - $367

Prices for flights from Milwaukee to Boston are currently below the regular range.

The regular price range for flights from Milwaukee to Boston is typically between $267 and $367. The current lowest deal is $196 with United Airlines, for travel from Aug 22 to Aug 28.

now $196

Low $267

High $367

The cheapest time to fly from Milwaukee to Boston

The cheapest month to fly from MKE to BOS is December, with a median price of $94. The most expensive month is August, with a median price of $619. Prices are generally lower from January to December.

December

Cheapest

Flights from $94

August

Most Expensive

Flights from $619

Jan

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Milwaukee to Boston

JetBlue Airways

Last-minute flights going from Milwaukee to Boston

Wed, Jul 1

⌛ Last-Minute

MKE - Boston

Milwaukee (MKE) - Boston (BOS)

JetBlue Airways

$202

$223

One-way

Thu, Jul 2

⌛ Last-Minute

MKE - Boston

Milwaukee (MKE) - Boston (BOS)

United Airlines

$333

$197

One-way

Thu, Jul 2

⌛ Last-Minute

MKE - Boston

Milwaukee (MKE) - Boston (BOS)

United Airlines

$353

$264

One-way

Thu, Jul 2

⌛ Last-Minute

MKE - Boston

Milwaukee (MKE) - Boston (BOS)

United Airlines

$327

$277

One-way

Thu, Jul 2

⌛ Last-Minute

MKE - Boston

Milwaukee (MKE) - Boston (BOS)

Deutsche Luft Hansa

$352

$303

One-way

Fri, Jul 3

⌛ Last-Minute

MKE - Boston

Milwaukee (MKE) - Boston (BOS)

United Airlines

$340

$197

One-way

Biggest price drops on these dates for flights from Milwaukee to Boston

3 nights

Oct 17 - Oct 20

$345 → $196

43%

1 night

Oct 6 - Oct 7

$343 → $198

42%

1 night

Jul 3 - Jul 4

$340 → $197

42%

5 nights

Jul 2 - Jul 7

$333 → $197

41%

Popular Airports to fly from Milwaukee to Boston

Milwaukee - Boston route insights

💸 Price insights

Recent fares are above the typical level

Recent fares for MKE to BOS are above the typical level, with 7% of deals considered good.

📅 Best time to fly

Fly in December for the best prices

Historically, December is the cheapest month to fly from MKE to BOS, with a median price of $94.

⏱️ Flight duration

Connecting flights take 8h 40m

The median flight time for connecting flights from Milwaukee to Boston is 8h 40m.

✈️ Airlines & availability

Connecting flights are dominant

Only 10.2% of recent deals are for direct flights; connecting flights are more common.

🏆 Airline highlight

JetBlue Airways offers direct flights

JetBlue Airways has historically offered direct flights from Milwaukee to Boston.

🎯 Booking tip

Deals are frequent for this route

There are historically frequent deals for flights from Milwaukee to Boston, averaging 1.03 per day.

Milwaukee main airports to depart from

General Mitchell International (MKE)

Cheapest

General Mitchell International Airport is a great option for flights from Milwaukee to Boston.

📍 ~10 km from Milwaukee (reachable by car or public transport)

💸 Flights from ~$196

Boston main airports to arrive at

Logan International (BOS)

Cheapest

Boston Logan International Airport is ideal for direct access to Boston and surrounding areas.

📍 ~5 km from city center (reachable by car, public transport, or ferry)

💸 Flights from ~$196

Airports nearby Boston used as alternative

Rhode Island T. F. Green Int'l Airport (PVD)

This airport is a major regional alternative with a wide range of domestic and some international connections.

📍 ~48 km from Boston (reachable by car)

💸 Flights from ~$273

Manchester–Boston Regional (MHT)

This airport is a primary alternative for travelers north of Boston, with a strong domestic network.

📍 ~73 km from Boston (reachable by car)

💸 Flights from ~$340

Bradley International (BDL)

This large international airport serves as a major hub for Southern New England with diverse destination options.

📍 ~142 km from Boston (reachable by car)

💸 Flights from ~$273

Portland International Jetport (PWM)

This highly reliable regional jetport offers good connectivity for travelers heading to Maine.

📍 ~160 km from Boston (reachable by car)

💸 Flights from ~$285

Worcester Regional (ORH)

Cheapest

This airport is geographically close to the western Boston suburbs and offers a low-stress environment.

📍 ~65 km from Boston (reachable by car)

💸 Flights from ~$230

Business & First Class Flight Deals to Boston

Boston, United States

38% AI deal score

$5,061

Frequently Asked Questions About Flights to Boston

Historically, the best prices for flights from Milwaukee to Boston are found when booking between 28 and 59 days in advance. During this period, the average price was $239. Booking within 0-6 days of departure typically resulted in an average price of $338, while booking 7-13 days out saw an average of $259. Prices for bookings made 60+ days in advance were significantly higher, averaging $536.

Across the trailing quarter, a good deal for a flight from Milwaukee to Boston is considered to be $229 or less. The median price for this route was $284. Prices typically ranged up to $529 for the higher end of the market. Therefore, any price at or below $229 represents a favorable fare.

Historically, December has been the cheapest month to fly from Milwaukee to Boston, with a median price of $94. January also offered lower prices, with a median of $170. While July had a median price of $235, it was also identified as the most expensive month overall, compared to an annual median price of $284 for the route.

Related routes

Consider alternative routes from Milwaukee

Flights from Milwaukee to Amsterdam Flights from Milwaukee to Athens Flights from Milwaukee to Atlanta Flights from Milwaukee to Bangkok Flights from Milwaukee to Barcelona Flights from Milwaukee to Brussels Flights from Milwaukee to Calgary Flights from Milwaukee to Copenhagen Flights from Milwaukee to Dallas Flights from Milwaukee to Denver Flights from Milwaukee to Detroit Flights from Milwaukee to Dubai