$129+ Cheap flights from Boston to Milwaukee (BOS - MKE)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/7. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MKE
Oct 21 — Oct 281
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Boston to Milwaukee with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from Boston Logan Intl to Milwaukee-Mitchell are usually found in May or August, booked 47 days in advance, depart on a Saturday or Tuesday and return on a Wednesday
Cheap flight deals from Boston to Milwaukee
Cheapest
Best
Last-minute
One-way
Cheapest flights from Boston to MilwaukeeExplore the most affordable flight options available from Boston to Milwaukee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 21, 2026.
Explore the most affordable flight options available from Boston to Milwaukee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 21, 2026.
This Southwest deal was found by Cheapflights users on 9/16. 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 10/215:15 am -
1 stop5h 30m
Wed 11/46:35 am -
1 stop6h 55m
Deal found 9/16![Southwest logo]()
$258
This Southwest deal was found by Cheapflights users on 9/17. 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 10/145:35 am -
1 stop7h 20m
Sat 10/172:05 pm -
1 stop4h 45m
Deal found 9/17![Southwest logo]()
$270
This Southwest deal was found by Cheapflights users on 9/16. 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.
Thu 10/155:25 am -
1 stop5h 20m
Sat 10/172:50 pm -
1 stop4h 45m
Deal found 9/16![Southwest logo]()
$276
This Southwest deal was found by Cheapflights users on 9/17. 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 10/76:30 pm -
1 stop4h 50m
Tue 10/1310:20 am -
1 stop5h 50m
Deal found 9/17![Southwest logo]()
$282
This Southwest deal was found by Cheapflights users on 9/17. 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.
Thu 10/225:25 am -
1 stop5h 20m
Wed 11/44:15 pm -
1 stop5h 15m
Deal found 9/17![Southwest logo]()
$289
This Southwest deal was found by Cheapflights users on 9/18. 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.
Tue 10/272:50 pm -
2 stops9h 10m
Thu 10/296:50 pm -
1 stop4h 20m
Deal found 9/18![Southwest logo]()
$294
This Southwest deal was found by Cheapflights users on 9/17. 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 12/45:10 am -
1 stop5h 30m
Sat 12/56:15 am -
1 stop7h 05m
Deal found 9/17![Southwest logo]()
$307
This Southwest deal was found by Cheapflights users on 9/17. 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.
Thu 11/55:20 am -
1 stop5h 25m
Fri 11/66:25 pm -
1 stop4h 30m
Deal found 9/17![Southwest logo]()
$325
This Cheapflightsfares deal was found by Cheapflights users on 9/17. 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.
Tue 10/138:23 am -
Nonstop2h 32m
Wed 10/1410:46 am -
Nonstop2h 13m
Deal found 9/17![JetBlue logo]()
$328
Best flights from Boston to MilwaukeeDiscover carefully curated flight deals from Boston to Milwaukee that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 21, 2026.
Discover carefully curated flight deals from Boston to Milwaukee that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 21, 2026.
This Southwest deal was found by Cheapflights users on 9/17. 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.
Thu 12/173:30 pm -
2 stops9h 00m
Thu 12/316:20 am -
2 stops7h 10m
Deal found 9/17![Southwest logo]()
$373
This United Airlines deal was found by Cheapflights users on 9/19. 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 12/42:58 pm -
1 stop4h 50m
Sat 12/55:00 am -
2 stops7h 24m
Deal found 9/19![United Airlines logo]()
$383
This Delta deal was found by Cheapflights users on 9/18. 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 10/26:00 pm -
1 stop5h 21m
Mon 10/56:35 pm -
Nonstop2h 31m
Deal found 9/18![Delta logo]()
$447
This Southwest deal was found by Cheapflights users on 9/18. 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 12/117:25 am -
1 stop5h 40m
Mon 12/148:00 am -
2 stops7h 25m
Deal found 9/18![Southwest logo]()
$396
This United Airlines deal was found by Cheapflights users on 9/17. 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.
Sun 12/205:45 am -
2 stops7h 30m
Wed 12/307:00 pm -
1 stop5h 18m
Deal found 9/17![United Airlines logo]()
$433
This Southwest deal was found by Cheapflights users on 9/20. 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.
Tue 11/245:15 am -
1 stop5h 15m
Fri 11/275:30 am -
2 stops8h 00m
Deal found 9/20![Southwest logo]()
$416
This United Airlines deal was found by Cheapflights users on 9/16. 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 11/133:01 pm -
1 stop6h 49m
Mon 11/162:23 pm -
2 stops8h 36m
Deal found 9/16![United Airlines logo]()
$472
This Southwest deal was found by Cheapflights users on 9/19. 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 11/63:30 pm -
2 stops9h 05m
Sun 11/85:30 am -
2 stops8h 00m
Deal found 9/19![Southwest logo]()
$437
This Southwest deal was found by Cheapflights users on 9/18. 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.
Thu 11/125:35 am -
2 stops10h 20m
Thu 11/124:05 pm -
2 stops6h 50m
Deal found 9/18![Southwest logo]()
$437
This Southwest deal was found by Cheapflights users on 9/17. 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.
Thu 10/155:35 am -
2 stops10h 30m
Thu 10/226:50 pm -
1 stop4h 20m
Deal found 9/17![Southwest logo]()
$452
This Southwest deal was found by Cheapflights users on 9/18. 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 10/166:45 pm -
1 stop5h 25m
Sun 10/185:55 am -
2 stops6h 50m
Deal found 9/18![Southwest logo]()
$472
This Southwest deal was found by Cheapflights users on 9/20. 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 12/193:00 pm -
2 stops10h 10m
Mon 1/184:35 pm -
1 stop4h 35m
Deal found 9/20![Southwest logo]()
$508
Last-minute flights from Boston to MilwaukeeDiscover last-minute flight deals from Boston to Milwaukee. Data last updated September 21, 2026 and is based on user searches.
Discover last-minute flight deals from Boston to Milwaukee. Data last updated September 21, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 9/17. 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 10/76:30 pm -
1 stop4h 50m
Tue 10/1310:20 am -
1 stop5h 50m
Deal found 9/17![Southwest logo]()
$282
This Cheapflightsfares deal was found by Cheapflights users on 9/17. 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.
Tue 10/138:23 am -
Nonstop2h 32m
Wed 10/1410:46 am -
Nonstop2h 13m
Deal found 9/17![JetBlue logo]()
$328
This Southwest deal was found by Cheapflights users on 9/17. 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 10/145:35 am -
1 stop7h 20m
Sat 10/172:05 pm -
1 stop4h 45m
Deal found 9/17![Southwest logo]()
$270
This Southwest deal was found by Cheapflights users on 9/16. 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.
Thu 10/155:25 am -
1 stop5h 20m
Sat 10/172:50 pm -
1 stop4h 45m
Deal found 9/16![Southwest logo]()
$276
This Southwest deal was found by Cheapflights users on 9/16. 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 10/215:15 am -
1 stop5h 30m
Wed 11/46:35 am -
1 stop6h 55m
Deal found 9/16![Southwest logo]()
$258
This American Airlines deal was found by Cheapflights users on 9/17. 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 10/2112:55 pm -
1 stop5h 37m
Wed 11/411:38 am -
1 stop4h 30m
Deal found 9/17![American Airlines logo]()
$337
This Southwest deal was found by Cheapflights users on 9/17. 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.
Thu 10/225:25 am -
1 stop5h 20m
Wed 11/44:15 pm -
1 stop5h 15m
Deal found 9/17![Southwest logo]()
$289
This Southwest deal was found by Cheapflights users on 9/18. 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.
Tue 10/272:50 pm -
2 stops9h 10m
Thu 10/296:50 pm -
1 stop4h 20m
Deal found 9/18![Southwest logo]()
$294
One-way flights from Boston to MilwaukeeSearch for one-way flight options from Boston to Milwaukee. Find affordable one-way fares based on user searches. Data last updated September 21, 2026.
Search for one-way flight options from Boston to Milwaukee. Find affordable one-way fares based on user searches. Data last updated September 21, 2026.
This Southwest deal was found by Cheapflights users on 9/16. 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 10/75:15 am -
1 stop5h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Southwest logo]()
$129
This Southwest deal was found by Cheapflights users on 9/16. 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 12/167:55 am -
1 stop5h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Southwest logo]()
$135
This Cheapflightsfares deal was found by Cheapflights users on 9/18. 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.
Sat 10/2411:47 am -
1 stop22h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Frontier logo]()
$143
This Frontier deal was found by Cheapflights users on 9/20. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/2211:06 am -
1 stop7h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Frontier logo]()
$144
This Southwest deal was found by Cheapflights users on 9/16. 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.
Thu 10/155:25 am -
1 stop5h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Southwest logo]()
$147
This Southwest deal was found by Cheapflights users on 9/17. 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.
Mon 11/165:35 pm -
1 stop4h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Southwest logo]()
$154
This Frontier deal was found by Cheapflights users on 9/20. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/2311:06 am -
1 stop7h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Frontier logo]()
$159
This KAYAK deal was found by Cheapflights users on 9/16. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/78:30 am -
Nonstop2h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![JetBlue logo]()
$166
This Super.com deal was found by Cheapflights users on 9/16. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/1911:47 am -
1 stop22h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Frontier logo]()
$168
This American Airlines deal was found by Cheapflights users on 9/17. 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 10/77:00 am -
1 stop5h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![American Airlines logo]()
$169
Find flight deals from Boston to Milwaukee
Discover tips and strategies to find the most affordable flight options for your journey from Boston (BOS) to Milwaukee (MKE). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 21, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $258 (Southwest) |
One-way from | $129 (Southwest) |
Popular in | November |
Cheapest in | May |
Average price | $315 |
Good round-trip deal | $318 or less |
Good one-way deal | $278 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Boston to Milwaukee 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 7,457,451 searches. Data last updated September 21, 2026.
Use the filters below to find and compare flights from Boston to Milwaukee that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
BostonMilwaukee
BOS Boston Logan Intl - MKE Milwaukee-Mitchell
BOSMKE
Boston Logan Intl
Mon 11/16
5:35 pm-9:25 pm
1 stop4h 50m
Milwaukee-Mitchell
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$154
BostonMilwaukee
BOS Boston Logan Intl - MKE Milwaukee-Mitchell
BOSMKE
Boston Logan Intl
Tue 10/20
5:45 am-11:30 am
2 stops6h 45m
Milwaukee-Mitchell
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$174
BostonMilwaukee
BOS Boston Logan Intl - MKE Milwaukee-Mitchell
BOSMKE
Boston Logan Intl
Thu 10/22
5:25 am-9:45 am
1 stop5h 20m
Milwaukee-Mitchell
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$189
BostonMilwaukee
BOS Boston Logan Intl - MKE Milwaukee-Mitchell
BOSMKE
Boston Logan Intl
Wed 12/9
5:30 am-11:00 am
2 stops6h 30m
Milwaukee-Mitchell
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$194
BostonMilwaukee
BOS Boston Logan Intl - MKE Milwaukee-Mitchell
BOSMKE
Boston Logan Intl
Sat 10/31
7:20 am-4:50 pm
2 stops10h 30m
Milwaukee-Mitchell
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$194
BostonMilwaukee
BOS Boston Logan Intl - MKE Milwaukee-Mitchell
BOSMKE
Boston Logan Intl
Sat 10/24
5:45 am-11:30 am
2 stops6h 45m
Milwaukee-Mitchell
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$199
BostonMilwaukee
BOS Boston Logan Intl - MKE Milwaukee-Mitchell
BOSMKE
Boston Logan Intl
Sun 12/20
5:45 am-12:15 pm
2 stops7h 30m
Milwaukee-Mitchell
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$199
BostonMilwaukee
BOS Boston Logan Intl - MKE Milwaukee-Mitchell
BOSMKE
Boston Logan Intl
Thu 10/15
6:00 am-9:56 am
1 stop4h 56m
Milwaukee-Mitchell
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$219
BostonMilwaukee
BOS Boston Logan Intl - MKE Milwaukee-Mitchell
BOSMKE
Boston Logan Intl
Wed 11/11
6:00 am-5:43 pm
3 stops12h 43m
Milwaukee-Mitchell
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$219
BostonMilwaukee
BOS Boston Logan Intl - MKE Milwaukee-Mitchell
BOSMKE
Boston Logan Intl
Wed 11/18
10:30 am-6:58 pm
2 stops9h 28m
Milwaukee-Mitchell
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$224
Showing 1-10 of 22 resultsSorted by cheapest first
Compare providers for flights from Boston to Milwaukee
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Boston to Milwaukee in September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Boston-Milwaukee flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Boston-Milwaukee flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Boston-Milwaukee flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Boston-Milwaukee flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Boston-Milwaukee flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Boston to Milwaukee
Have a flexible travel schedule? Discover the best time to fly to Milwaukee from Boston with our price prediction graph.
BOS-MKE
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 Boston to Milwaukee
Prices
Airlines
How far ahead should I book a flight from Boston to Milwaukee?
To ensure you get the cheapest price possible for a flight from Boston to Milwaukee, you should look to book at least 46 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
What is the cheapest month to book a flight from Boston to Milwaukee?
Currently, May is the cheapest month in which you can book a flight from Boston to Milwaukee (average of $272). Flying from Boston to Milwaukee in November is currently the most expensive (average of $486). 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 BOS to MKE?
Find hourly flight availability from Boston to Milwaukee. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 21, 2026.
It’s typically best to fly out from Boston to Milwaukee at noon. Doing so could potentially save you 23% on the flight price compared to flying in the afternoon, which is usually more expensive.
What is the cheapest day to fly from Boston to Milwaukee?
Use this chart to determine the cheapest time to fly round-trip from Boston to Milwaukee. Price data was last updated on September 19, 2026.
Travelers seeking maximum savings on their Boston to Milwaukee flight should consider departing on Wednesday at noon when fares are most often at their lowest. Monday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Milwaukee
Get insights into the airlines that provide service to Milwaukee. 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 Milwaukee. Reviews last updated September 21, 2026.
Get a feel of what it's like to fly with Southwest,Delta, andUnited Airlines from Boston to Milwaukee by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
7.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Crew
8.6
Overall
8.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Food
7.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Crew
8.6
Overall
8.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Food
7.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Crew
8.6
Overall
8.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Food
7.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Crew
8.6
Overall
8.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Food
7.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Crew
8.6
Overall
8.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Food
7.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Crew
8.6
Overall
8.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Related info for your journey
Find useful and relevant information for your journey from Boston to Milwaukee. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Milwaukee?
Book flights to Milwaukee if you plan to visit one of these locationsPort Washington
Sheboygan
New Berlin
Oak Creek
Wauwatosa
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Milwaukee flight routes
Other flight options
Other flights from Boston
Popular flights
Alternative routes for Boston to Milwaukee
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Milwaukee by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Boston to Milwaukee by cabin class
Find flights from Boston to Milwaukee, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Other flights to Milwaukee
Explore flights to Milwaukee departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 21, 2026.
Boston and Milwaukee flights
Browse other Boston and Milwaukee flight options. Last updated on September 21, 2026.
Other flights from Boston
Browse through other flights departing from Boston. Flights are based on user searches made on Cheapflights and were last updated on September 21, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 5 airlines flying from Boston to Milwaukee
Discover the top 5 airlines that operate flights from Boston to Milwaukee. 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 7,457,451 searches. Data last updated September 21, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$116 | Average$266 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$124 | Average$380 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$196 | Average$403 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$206 | Average$326 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$207 | Average$316 | FlexibilityNo cancel fee | On-time63% |