How many flights from Boston to Milwaukee are non-stop?

Across the trailing 90 days, 56.3% of flights from Boston to Milwaukee were non-stop. For flights that included stopovers, travelers typically encountered a median of 2 stopovers. This indicates that while direct options are available, connecting flights are also a significant portion of the route's offerings.

How long does it take to fly from Boston to Milwaukee?

A direct flight from Boston to Milwaukee typically takes 2 hours and 35 minutes, covering a distance of 1381 kilometers. For flights with one stop, the median travel time extends to 5 hours and 40 minutes. This accounts for the additional time spent during layovers.

Are there frequently good prices on flights from Boston to Milwaukee?

Historically, good prices on flights from Boston to Milwaukee have been frequent. This route is classified as one that regularly offers competitive fares. Travelers can often find favorable deals when planning their trips between these two cities.

Flights From Boston

To Milwaukee

Cheap Flights from Boston to Milwaukee

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

Deals from

Boston

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

Prices updated 1 day ago

461 airlines compared

80%+ AI score for best value

Fares are subject to change and may not be available for all dates. (Data last updated Sep 14, 2026.)

Today’s best flight deals from Boston to Milwaukee

Explore current cheapest deals departing from Boston to Milwaukee

2026-12-03 – 2026-12-07
BOS - Milwaukee
68% AI deal score
$357
$284
Round trip
2026-12-04 – 2026-12-07
BOS - Milwaukee
67% AI deal score
$359
$301
Round trip
2026-10-06 – 2026-10-07
BOS - Milwaukee
44% AI deal score
$178
$314
Round trip
2026-10-21 – 2026-10-26
BOS - Milwaukee
49% AI deal score
$338
$318
Round trip
2026-10-27 – 2026-10-28
BOS - Milwaukee
49% AI deal score
$343
$321
Round trip
2026-09-30 – 2026-10-07
BOS - Milwaukee
44% AI deal score
$163
$329
Round trip
2026-09-29 – 2026-10-07
BOS - Milwaukee
44% AI deal score
$157
$329
Round trip
2026-09-30 – 2026-10-06
BOS - Milwaukee
44% AI deal score
$163
$329
Round trip
2026-09-29 – 2026-10-06
BOS - Milwaukee
44% AI deal score
$164
$329
Round trip
2026-10-06 – 2026-10-13
BOS - Milwaukee
44% AI deal score
$169
$332
Round trip

Boston to Milwaukee: Overview

Insights for flights from Boston to Milwaukee

For cheap flights from Boston to Milwaukee, the data indicates that January is typically the most affordable month to fly, with a median fare of $138. Other cost-effective options include March, with a median fare of $147, and September, where the median fare is $217. Planning your trip around these months could lead to more favorable pricing.

Fares for flights from Boston to Milwaukee typically range from $217 to $639, with a median of $229. Right now, current fares are below the typical level for this route. Only 6% of recent fares were classified as a good price, suggesting that finding exceptionally low prices can be challenging. New deals for this route appear almost daily, making it beneficial to monitor prices regularly.

When flying from Boston to Milwaukee, a meaningful share of itineraries are non-stop, while the rest connect once. Specifically, 56.3% of recent fares were for direct flights from Boston to Milwaukee. For itineraries that include connections, the typical number of stopovers is 2.

A typical journey from Boston to Milwaukee takes approximately 5h 29m, including connections. This duration reflects the overall travel time, accounting for both direct flights and those with one or more stopovers. The total distance covered on this route is 1381 kilometers, classifying it as a short-haul flight.

How much is a round trip from Boston to Milwaukee

Regular price: $281 - $433

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

The regular price range for flights from Boston to Milwaukee is $281 to $433. The current lowest deal is $286 with Southwest Airlines, for travel from Dec 3-Dec 7.

now $286

Low $281

High $433

The cheapest time to fly from Boston to Milwaukee

The cheapest month to fly from Boston to Milwaukee is January, with a median price of $138. The most expensive month is July, with a median price of $609. Prices are generally lower from January to October.

January

Cheapest

Flights from $138

July

Most Expensive

Flights from $609

Jan

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Direct flights from Boston to Milwaukee

JetBlue Airways

Last-minute flights going from Boston to Milwaukee

Fri, Sep 18

⌛ Last-Minute

BOS - Milwaukee

Boston (BOS) - Milwaukee (MKE)

American Airlines

$551

$553

One-way

Mon, Sep 21

⌛ Last-Minute

BOS - Milwaukee

Boston (BOS) - Milwaukee (MKE)

United Airlines

$385

$471

One-way

Thu, Sep 24

⌛ Last-Minute

BOS - Milwaukee

Boston (BOS) - Milwaukee (MKE)

JetBlue Airways

$199

$342

One-way

Fri, Sep 25

⌛ Last-Minute

BOS - Milwaukee

Boston (BOS) - Milwaukee (MKE)

JetBlue Airways

$199

$394

One-way

Sat, Sep 26

⌛ Last-Minute

BOS - Milwaukee

Boston (BOS) - Milwaukee (MKE)

JetBlue Airways

$194

$336

One-way

Sat, Sep 26

⌛ Last-Minute

BOS - Milwaukee

Boston (BOS) - Milwaukee (MKE)

JetBlue Airways

$196

$359

One-way

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

4 nights

Dec 3 - Dec 7

$357 → $286

20%

3 nights

Dec 4 - Dec 7

$359 → $302

16%

3 nights

Sep 22 - Sep 25

$415 → $380

1 night

Oct 27 - Oct 28

$343 → $321

Popular Airports to fly from Boston to Milwaukee

Boston - Milwaukee route insights

💸 Price insights

Recent fares are below the typical level.

Recent fares for Boston to Milwaukee are below the typical level, at $286.

📅 Best time to fly

January offers the lowest median prices.

Historically, January has the lowest median price at $138, followed by March at $147.

⏱️ Flight duration

Flights typically take 5h 29m.

The median flight duration from Boston to Milwaukee is 5 hours and 29 minutes.

✈️ Airlines & availability

Deals are frequent on this route.

Deals on flights from Boston to Milwaukee are frequent, with 56.3% being direct.

🏆 Airline highlight

JetBlue Airways offers direct flights.

JetBlue Airways is one airline offering direct flights on the Boston to Milwaukee route.

🎯 Booking tip

Good prices are available 6% of the time.

Historically, good prices are available 6% of the time for flights from Boston to Milwaukee.

Boston main airports to depart from

Logan International (BOS)

Cheapest

Boston Logan International Airport (BOS) is a convenient departure point for flights to Milwaukee.

📍 ~4 km from Boston city center (reachable by car, bus, or subway)

💸 Flights from ~$288

Milwaukee main airports to arrive at

General Mitchell International (MKE)

Cheapest

General Mitchell International Airport is a convenient arrival choice for flights from Boston to Milwaukee.

📍 ~10 km from city center (reachable by car)

💸 Flights from ~$276

Airports nearby Milwaukee used as alternative

O Hare International (ORD)

Cheapest

Chicago O'Hare offers significantly more flight options and often lower fares due to high carrier competition.

📍 ~100 km from Milwaukee (reachable by bus or train)

💸 Flights from ~$178

Business & First Class Flight Deals to Milwaukee

$902

Save $370

United Airlines

Business Class

Frequently Asked Questions About Flights to Milwaukee

Historically, the optimal booking window for flights from Boston to Milwaukee has been 7-13 days before departure. During this period, the average price was $226. Booking 14-27 days out typically saw prices rise to an average of $266. For travelers booking 28-59 days in advance, the average fare was $490, while those booking 60+ days out faced the highest average price of $585 across the trailing quarter.

Across the trailing 90 days, a good price for a flight from Boston to Milwaukee was considered to be $217 or less. The median price for this route was $229. Prices typically began to increase significantly above the median, with 75% of fares being $639 or less.

Historically, January has offered some of the most affordable flights from Boston to Milwaukee, with a median price of $138. March also presented lower fares, with a median of $147. While September had a median price of $217, it was also observed as the most expensive month on average across the trailing 270 days, with the annual median price for the route being $229.

Related routes

More routes from Boston

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Flights to Milwaukee from other cities

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Boston to Milwaukee: Overview

Insights for flights from Boston to Milwaukee

How much is a round trip from Boston to Milwaukee

Regular price: $281 - $433

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

The regular price range for flights from Boston to Milwaukee is $281 to $433. The current lowest deal is $286 with Southwest Airlines, for travel from Dec 3-Dec 7.

now $286

Low $281

High $433

The cheapest time to fly from Boston to Milwaukee

January

Cheapest

Flights from $138

July

Most Expensive

Flights from $609

Jan

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct