To Milwaukee

Cheap Flights from Boston to Milwaukee

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Deals from

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

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 Boston to Milwaukee

Explore current cheapest deals departing from Boston to Milwaukee

Round trip

Sort by: Cheapest

July 9 - July 13

Cheapest

BOS - Milwaukee

$361

$196

Round trip

November 19 - November 26

Cheapest

BOS - Milwaukee

$360

$196

Round trip

July 15 - July 21

BOS - Milwaukee

$337

$197

Round trip

August 18 - August 25

BOS - Milwaukee

$340

$197

Round trip

October 14 - October 21

Best

BOS - Milwaukee

$377

$197

Round trip

October 3 - October 5

BOS - Milwaukee

$376

$197

Round trip

July 25 - July 28

BOS - Milwaukee

$342

$198

Round trip

July 3 - July 7

Earliest

BOS - Milwaukee

$373

$198

Round trip

August 27 - August 29

BOS - Milwaukee

$356

$198

Round trip

August 11 - August 14

BOS - Milwaukee

$357

$198

Round trip

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

Route Intelligence — 486,190 Searches this Week

Insights for flights from Boston to Milwaukee

For cheap flights from Boston to Milwaukee, January stands out as the most affordable month, with a median fare of just $138. Following closely, March also offers competitive prices, with a median fare of $147. Travelers can also find relatively lower prices in September, where the median fare is $217.

Fares for flights from Boston to Milwaukee typically range from $219–$752, with a median of $245. Right now, current fares are below the typical level for this route. Only 5% of recent fares were classified as a good price, indicating that finding exceptional deals can be challenging.

When flying from Boston to Milwaukee, a meaningful share of itineraries are non-stop, with 50% of recent fares being direct flights. For the remaining itineraries, most connecting flights typically involve two stopovers.

A typical journey from Boston to Milwaukee, including connections, takes approximately 5h 29m. This duration accounts for both direct and connecting itineraries, providing a realistic expectation for your travel time.

The distance between Boston and Milwaukee is 1381 kilometers. This makes it a short-haul route, generally indicating a quicker travel experience compared to longer international or transcontinental flights.

How much is a round trip from Boston to Milwaukee

Regular price: $292 - $447

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

Regular prices for flights from Boston to Milwaukee typically range from $292 to $447. The current lowest deal is $196 with American Airlines, for travel from July 9 to July 13.

now $196

Low $292

High $447

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, Jun 26

⌛ Last-Minute

BOS - Milwaukee

Boston (BOS) - Milwaukee (MKE)

American Airlines

$428

$331

One-way

Sat, Jun 27

⌛ Last-Minute

BOS - Milwaukee

Boston (BOS) - Milwaukee (MKE)

United Airlines

$428

$321

One-way

Wed, Jul 1

⌛ Last-Minute

BOS - Milwaukee

Boston (BOS) - Milwaukee (MKE)

JetBlue Airways

$204

$223

One-way

Wed, Jul 1

⌛ Last-Minute

BOS - Milwaukee

Boston (BOS) - Milwaukee (MKE)

American Airlines

$323

$232

One-way

Wed, Jul 1

⌛ Last-Minute

BOS - Milwaukee

Boston (BOS) - Milwaukee (MKE)

Frontier Airlines

$327

$251

One-way

Wed, Jul 1

⌛ Last-Minute

BOS - Milwaukee

Boston (BOS) - Milwaukee (MKE)

Deutsche Luft Hansa

$384

$257

One-way

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

7 nights

Oct 14 - Oct 21

$377 → $197

48%

2 nights

Oct 3 - Oct 5

$376 → $197

48%

4 nights

Jul 3 - Jul 7

$373 → $198

47%

4 nights

Jul 9 - Jul 13

$361 → $196

46%

Popular Airports to fly from Boston to Milwaukee

Boston - Milwaukee route insights

💸 Price insights

Recent fares are below the typical level.

Recent fares from Boston to Milwaukee are below the typical level at $196.

📅 Best time to fly

January is historically the cheapest month to fly.

Historically, January is the cheapest month to fly from Boston to Milwaukee, with a median price of $138.

⏱️ Flight duration

Flights are typically 5h 29m long.

Flights from Boston to Milwaukee typically take 5 hours and 29 minutes, covering 1381 km.

✈️ Airlines & availability

Deals appear frequently for this route.

Deals for flights from Boston to Milwaukee appear frequently, with 0.77 deals per day.

🏆 Airline highlight

JetBlue Airways offers direct flights.

JetBlue Airways is an airline that offers direct flights from Boston to Milwaukee.

🎯 Booking tip

5% of deals are considered good.

Historically, 5% of deals for flights from Boston to Milwaukee are considered good prices.

Boston main airports to depart from

Logan International (BOS)

Cheapest

Boston Logan International Airport is a convenient choice for flights from Boston to Milwaukee.

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

💸 Flights from ~$196

Milwaukee main airports to arrive at

General Mitchell International (MKE)

Cheapest

General Mitchell International Airport is the primary airport serving Milwaukee, Wisconsin, and surrounding areas.

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

💸 Flights from ~$196

Airports nearby Milwaukee used as alternative

O Hare International (ORD)

Cheapest

Consider ORD for significantly more flight options and direct shuttle services to Milwaukee.

📍 ~120 km from Milwaukee (reachable by shuttle bus)

💸 Flights from ~$127

Chicago Midway International (MDW)

MDW is a primary hub for Southwest Airlines, offering competitive domestic pricing and less congestion.

📍 ~100 km from Milwaukee (reachable by car)

💸 Flights from ~$142

Dane County Regional (MSN)

MSN is a convenient, low-stress regional alternative with an easy drive from Milwaukee.

📍 ~125 km from Milwaukee (reachable by car)

💸 Flights from ~$287

Appleton International (ATW)

ATW is a viable alternative for travelers in northern Milwaukee suburbs, offering easy parking and navigation.

📍 ~140 km from Milwaukee (reachable by car)

💸 Flights from ~$267

Green Bay–Austin Straubel International (GRB)

GRB serves as an alternative regional gateway for northern Wisconsin destinations with reliable service.

📍 ~180 km from Milwaukee (reachable by car)

💸 Flights from ~$289

Business & First Class Flight Deals to Milwaukee

Milwaukee, United States

38% AI deal score

$4,438

From BOS

Elite

Jul 02

Milwaukee, United States

38% AI deal score

$4,818

Frequently Asked Questions About Flights to Milwaukee

Historically, the best time to purchase tickets for flights from Boston to Milwaukee is typically 7-13 days before departure. During this window, the average price for a ticket was $226. Prices tend to increase as the departure date approaches, with tickets bought 14-27 days out averaging $266, and those purchased 60+ days in advance costing around $585. These trends are based on data from the trailing 90 days.

Across the trailing quarter, a good price for a flight from Boston to Milwaukee is considered to be $219 or less. The median price for this route was $245. For comparison, 75% of tickets were priced at $752 or less. This threshold is based on an analysis of prices over the last 90 days.

Historically, January and March have offered the cheapest flights from Boston to Milwaukee. In January, the median price was $138, while in March, it was $147. September also presented a relatively lower median price of $217. The annual median price for this route was $245, based on data from the trailing 270 days.

Related routes

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Cheap Flights from Boston to Milwaukee

Today’s best flight deals from Boston to Milwaukee

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

Route Intelligence — 486,190 Searches this Week

Insights for flights from Boston to Milwaukee

How much is a round trip from Boston to Milwaukee

The cheapest time to fly from Boston to Milwaukee

Direct flights from Boston to Milwaukee

Last-minute flights going from Boston to Milwaukee

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

Popular Airports to fly from Boston to Milwaukee

Boston - Milwaukee route insights

Recent fares are below the typical level.

January is historically the cheapest month to fly.

Flights are typically 5h 29m long.

Deals appear frequently for this route.

JetBlue Airways offers direct flights.

5% of deals are considered good.

Boston main airports to depart from

Milwaukee main airports to arrive at

Airports nearby Milwaukee used as alternative

Business & First Class Flight Deals to Milwaukee

Best Elite deals to Milwaukee

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Frequently Asked Questions About Flights to Milwaukee

When should I buy Boston to Milwaukee tickets?

When should I buy Boston to Milwaukee tickets?