$129+ Cheap flights from Massachusetts to Milwaukee (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 12/1. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MKE
Nov 19 — Nov 261
Round-trip
1 adult, Economy
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Find cheap flights from Massachusetts to Milwaukee with Cheapflights
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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
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Cheapest flights from Massachusetts to MilwaukeeExplore the most affordable flight options available from Massachusetts to Milwaukee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 20, 2026.
Explore the most affordable flight options available from Massachusetts to Milwaukee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 20, 2026.
This Southwest deal was found by Cheapflights users on 10/19. 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 11/65:10 am -
1 stop5h 30m
Mon 11/96:25 pm -
1 stop4h 30m
Deal found 10/19![Southwest logo]()
$333
This Southwest deal was found by Cheapflights users on 10/18. 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 11/136:30 pm -
1 stop4h 45m
Mon 11/166:35 am -
1 stop6h 55m
Deal found 10/18![Southwest logo]()
$335
This American Airlines deal was found by Cheapflights users on 10/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/136:00 am -
1 stop7h 06m
Sun 12/134:54 pm -
1 stop5h 59m
Deal found 10/16![American Airlines logo]()
$337
This American Airlines deal was found by Cheapflights users on 10/15. 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 11/1810:19 am -
1 stop7h 19m
Wed 12/28:41 am -
1 stop5h 58m
Deal found 10/15![American Airlines logo]()
$348
This American Airlines deal was found by Cheapflights users on 10/19. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/65:36 pm -
1 stop19h 28m
Mon 11/96:00 am -
1 stop10h 07m
Deal found 10/19![American Airlines logo]()
$350
This Delta deal was found by Cheapflights users on 10/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/64:10 pm -
1 stop6h 14m
Mon 11/95:20 am -
2 stops8h 59m
Deal found 10/17![Delta logo]()
$360
This Southwest deal was found by Cheapflights users on 10/19. 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.
Tue 11/175:00 am -
1 stop10h 05m
Tue 11/245:20 pm -
1 stop4h 05m
Deal found 10/19![Southwest logo]()
$361
This American Airlines deal was found by Cheapflights users on 10/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/2312:47 pm -
1 stop5h 58m
Sun 12/67:00 am -
1 stop5h 48m
Deal found 10/18![American Airlines logo]()
$368
This Southwest deal was found by Cheapflights users on 10/18. 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.
Sat 12/55:25 am -
2 stops6h 40m
Sat 12/51:45 pm -
2 stops7h 15m
Deal found 10/18![Southwest logo]()
$372
This American Airlines deal was found by Cheapflights users on 10/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/75:36 pm -
1 stop19h 28m
Mon 11/92:55 pm -
2 stops25h 12m
Deal found 10/16![American Airlines logo]()
$444
This American Airlines deal was found by Cheapflights users on 10/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/235:16 pm -
1 stop5h 38m
Sun 10/257:19 pm -
2 stops20h 30m
Deal found 10/16![American Airlines logo]()
$665
This American Airlines deal was found by Cheapflights users on 10/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/225:16 pm -
2 stops26h 20m
Sun 10/257:19 pm -
2 stops20h 30m
Deal found 10/16![American Airlines logo]()
$739
Best flights from Massachusetts to MilwaukeeDiscover carefully curated flight deals from Massachusetts to Milwaukee that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 20, 2026.
Discover carefully curated flight deals from Massachusetts to Milwaukee that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 20, 2026.
This American Airlines deal was found by Cheapflights users on 10/19. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/65:36 pm -
1 stop19h 28m
Mon 11/96:00 am -
1 stop10h 07m
Deal found 10/19![American Airlines logo]()
$350
This Delta deal was found by Cheapflights users on 10/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/64:10 pm -
1 stop6h 14m
Mon 11/95:20 am -
2 stops8h 59m
Deal found 10/17![Delta logo]()
$360
This Southwest deal was found by Cheapflights users on 10/15. 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 11/67:45 pm -
1 stop4h 50m
Mon 11/94:05 pm -
2 stops6h 50m
Deal found 10/15![Southwest logo]()
$376
This Southwest deal was found by Cheapflights users on 10/19. 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 12/185:15 am -
1 stop5h 15m
Mon 12/283:40 pm -
1 stop6h 50m
Deal found 10/19![Southwest logo]()
$387
This Delta deal was found by Cheapflights users on 10/18. 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.
Sat 12/123:15 pm -
Nonstop2h 53m
Mon 12/147:35 am -
Nonstop2h 27m
Deal found 10/18![Delta logo]()
$419
This American Airlines deal was found by Cheapflights users on 10/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/75:36 pm -
1 stop19h 28m
Mon 11/92:55 pm -
2 stops25h 12m
Deal found 10/16![American Airlines logo]()
$444
This Southwest deal was found by Cheapflights users on 10/16. 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 12/243:30 pm -
2 stops7h 50m
Fri 12/256:20 am -
2 stops8h 30m
Deal found 10/16![Southwest logo]()
$415
This Delta deal was found by Cheapflights users on 10/15. 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.
Thu 1/217:40 pm -
Nonstop2h 53m
Sun 1/2412:20 pm -
1 stop6h 01m
Deal found 10/15![Delta logo]()
$429
This Southwest deal was found by Cheapflights users on 10/19. 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.
Mon 11/23:30 pm -
2 stops9h 00m
Thu 11/56:55 am -
1 stop4h 20m
Deal found 10/19![Southwest logo]()
$439
This Delta deal was found by Cheapflights users on 10/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/2410:38 am -
Nonstop2h 52m
Thu 1/77:00 am -
Nonstop2h 23m
Deal found 10/16![Delta logo]()
$448
This Southwest deal was found by Cheapflights users on 10/17. 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.
Tue 11/32:25 pm -
2 stops8h 45m
Sat 11/75:45 am -
1 stop4h 10m
Deal found 10/17![Southwest logo]()
$439
This Southwest deal was found by Cheapflights users on 10/16. 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 12/235:00 pm -
1 stop7h 40m
Wed 1/66:00 am -
2 stops6h 50m
Deal found 10/16![Southwest logo]()
$446
This Southwest deal was found by Cheapflights users on 10/19. 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.
Thu 12/175:10 pm -
2 stops7h 00m
Mon 1/1810:15 am -
2 stops10h 10m
Deal found 10/19![Southwest logo]()
$455
This Southwest deal was found by Cheapflights users on 10/18. 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.
Wed 11/49:10 am -
2 stops9h 10m
Sat 11/71:45 pm -
2 stops7h 20m
Deal found 10/18![Southwest logo]()
$459
Last-minute flights from Massachusetts to MilwaukeeDiscover last-minute flight deals from Massachusetts to Milwaukee. Data last updated October 20, 2026 and is based on user searches.
Discover last-minute flight deals from Massachusetts to Milwaukee. Data last updated October 20, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 10/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/225:16 pm -
2 stops26h 20m
Sun 10/257:19 pm -
2 stops20h 30m
Deal found 10/16![American Airlines logo]()
$739
This American Airlines deal was found by Cheapflights users on 10/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/235:16 pm -
1 stop5h 38m
Sun 10/257:19 pm -
2 stops20h 30m
Deal found 10/16![American Airlines logo]()
$665
This Southwest deal was found by Cheapflights users on 10/19. 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 11/65:10 am -
1 stop5h 30m
Mon 11/96:25 pm -
1 stop4h 30m
Deal found 10/19![Southwest logo]()
$333
This American Airlines deal was found by Cheapflights users on 10/19. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/65:36 pm -
1 stop19h 28m
Mon 11/96:00 am -
1 stop10h 07m
Deal found 10/19![American Airlines logo]()
$350
This Delta deal was found by Cheapflights users on 10/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/64:10 pm -
1 stop6h 14m
Mon 11/95:20 am -
2 stops8h 59m
Deal found 10/17![Delta logo]()
$360
This American Airlines deal was found by Cheapflights users on 10/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/75:36 pm -
1 stop19h 28m
Mon 11/92:55 pm -
2 stops25h 12m
Deal found 10/16![American Airlines logo]()
$444
This Southwest deal was found by Cheapflights users on 10/18. 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 11/127:45 pm -
1 stop4h 50m
Sat 11/1410:50 am -
2 stops10h 15m
Deal found 10/18![Southwest logo]()
$381
This Southwest deal was found by Cheapflights users on 10/18. 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 11/136:30 pm -
1 stop4h 45m
Mon 11/166:35 am -
1 stop6h 55m
Deal found 10/18![Southwest logo]()
$335
This Southwest deal was found by Cheapflights users on 10/19. 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.
Tue 11/175:00 am -
1 stop10h 05m
Tue 11/245:20 pm -
1 stop4h 05m
Deal found 10/19![Southwest logo]()
$361
This American Airlines deal was found by Cheapflights users on 10/15. 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 11/1810:19 am -
1 stop7h 19m
Wed 12/28:41 am -
1 stop5h 58m
Deal found 10/15![American Airlines logo]()
$348
This American Airlines deal was found by Cheapflights users on 10/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/2312:47 pm -
1 stop5h 58m
Sun 12/67:00 am -
1 stop5h 48m
Deal found 10/18![American Airlines logo]()
$368
One-way flights from Massachusetts to MilwaukeeSearch for one-way flight options from Massachusetts to Milwaukee. Find affordable one-way fares based on user searches. Data last updated October 20, 2026.
Search for one-way flight options from Massachusetts to Milwaukee. Find affordable one-way fares based on user searches. Data last updated October 20, 2026.
This American Airlines deal was found by Cheapflights users on 10/15. 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.
Tue 12/15:40 am -
1 stop5h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![American Airlines logo]()
$129
This Super.com deal was found by Cheapflights users on 10/16. 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.
Sun 11/2211:06 am -
1 stop7h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/16![Frontier logo]()
$140
This Southwest deal was found by Cheapflights users on 10/19. 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.
Thu 11/195:30 am -
1 stop7h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Southwest logo]()
$142
This Southwest deal was found by Cheapflights users on 10/18. 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.
Mon 11/165:20 am -
1 stop5h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![Southwest logo]()
$147
This American Airlines deal was found by Cheapflights users on 10/19. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/243:37 pm -
1 stop7h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![American Airlines logo]()
$149
This Southwest deal was found by Cheapflights users on 10/19. 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 12/185:15 am -
1 stop5h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Southwest logo]()
$168
This Super.com deal was found by Cheapflights users on 10/15. 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 11/2311:06 am -
1 stop7h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![Frontier logo]()
$170
This Cheapflightsfares deal was found by Cheapflights users on 10/19. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/2611:47 am -
1 stop22h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Frontier logo]()
$184
This Kiwi.com deal was found by Cheapflights users on 10/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1812:39 pm -
2 stops21h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![Frontier logo]()
$185
This Southwest deal was found by Cheapflights users on 10/19. 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.
Sun 11/84:20 pm -
1 stop6h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Southwest logo]()
$186
This Southwest deal was found by Cheapflights users on 10/19. 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 11/135:35 am -
1 stop7h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Southwest logo]()
$188
This Southwest deal was found by Cheapflights users on 10/15. 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 11/101:20 pm -
2 stops9h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![Southwest logo]()
$191
Find flight deals from Massachusetts to Milwaukee
Keep the following information in mind while searching for Massachusetts to Milwaukee flight deals. Data was last updated October 20, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $333 (Southwest) |
One-way from | $129 (American Airlines) |
Popular in | November |
Cheapest in | May |
Average price | $405 |
Good round-trip deal | $399 or less |
Good one-way deal | $268 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Massachusetts 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 October 20, 2026.
Use the filters below to find and compare flights from Massachusetts to Milwaukee that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
BostonMilwaukee
BOS Boston Logan Intl - MKE Milwaukee-Mitchell
BOSMKE
Boston Logan Intl
Thu 11/19
5:30 am-12:00 pm
1 stop7h 30m
Milwaukee-Mitchell
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$142
BostonMilwaukee
BOS Boston Logan Intl - MKE Milwaukee-Mitchell
BOSMKE
Boston Logan Intl
Thu 11/5
5:35 am-12:05 pm
1 stop7h 30m
Milwaukee-Mitchell
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$186
BostonMilwaukee
BOS Boston Logan Intl - MKE Milwaukee-Mitchell
BOSMKE
Boston Logan Intl
Sat 11/14
5:35 am-11:50 am
1 stop7h 15m
Milwaukee-Mitchell
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$213
BostonMilwaukee
BOS Boston Logan Intl - MKE Milwaukee-Mitchell
BOSMKE
Boston Logan Intl
Wed 11/18
5:05 pm-9:30 pm
1 stop5h 25m
Milwaukee-Mitchell
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$213
Quickest round-trip
BostonMilwaukee
BOS Boston Logan Intl - MKE Milwaukee-Mitchell
BOSMKE
Boston Logan Intl
Sun 11/15
6:30 pm-8:27 pm
Nonstop2h 57m
Milwaukee-Mitchell
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$219
WorcesterMilwaukee
ORH Worcester - MKE Milwaukee-Mitchell
ORHMKE
Worcester
Thu 12/3
7:04 pm-12:08 pm
1 stop18h 04m
Milwaukee-Mitchell
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$220
BostonMilwaukee
BOS Boston Logan Intl - MKE Milwaukee-Mitchell
BOSMKE
Boston Logan Intl
Fri 12/18
2:35 pm-10:25 pm
2 stops8h 50m
Milwaukee-Mitchell
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$225
BostonMilwaukee
BOS Boston Logan Intl - MKE Milwaukee-Mitchell
BOSMKE
Boston Logan Intl
Thu 11/26
5:30 am-11:28 am
2 stops6h 58m
Milwaukee-Mitchell
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$234
BostonMilwaukee
BOS Boston Logan Intl - MKE Milwaukee-Mitchell
BOSMKE
Boston Logan Intl
Fri 11/6
2:25 pm-11:10 pm
2 stops9h 45m
Milwaukee-Mitchell
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$249
BostonMilwaukee
BOS Boston Logan Intl - MKE Milwaukee-Mitchell
BOSMKE
Boston Logan Intl
Thu 10/29
9:05 am-5:50 pm
2 stops9h 45m
Milwaukee-Mitchell
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$254
Showing 1-10 of 28 resultsSorted by cheapest first
Best time to book a flight from Massachusetts to Milwaukee
Have a flexible travel schedule? Discover the best time to fly to Milwaukee from Massachusetts with our price prediction graph.
BOS-MKE
ORH-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 Massachusetts to Milwaukee
USMA-MKE
BOS-MKE
ORH-MKE
What is the cheapest month to book a flight from Massachusetts to Milwaukee?
Currently, May is the cheapest month in which you can book a flight from Massachusetts to Milwaukee (average of $273). Flying from Massachusetts to Milwaukee in November is currently the most expensive (average of $499). 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 MA to MKE?
Find hourly flight availability from Massachusetts 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 October 20, 2026.
It’s optimal to fly from Massachusetts to Milwaukee at noon. By choosing this option you can save up to 20% on the cost of your flight, compared to a flight in the afternoon.
Weekly flight availability from Massachusetts to Milwaukee
Explore weekly flight availability from Massachusetts to Milwaukee. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated October 20, 2026.
The most flights from USMA to MKE are scheduled on a Sunday (8 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (3 on average).
How much does it cost to fly round-trip from Massachusetts to Milwaukee?
Airfare is below average for this route at the moment.
Massachusetts to Milwaukee flights typically cost between $368 and $628 in November.The cheapest round-trip price found within the last 5 days was $333 on Southwest (Nov 6-Nov 9).
How far ahead should I book a flight from Massachusetts to Milwaukee?
The best time to book flights from Massachusetts to Milwaukee is 67 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
Related info for your journey
Find useful and relevant information for your journey from Massachusetts 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
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Alternative routes for Massachusetts to Milwaukee
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Complete your trip
Complete your trip to Milwaukee by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Massachusetts to Milwaukee by cabin class
Find flights from Massachusetts 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 October 20, 2026.
Massachusetts and Milwaukee flights
Browse other Massachusetts and Milwaukee flight options. Last updated on October 20, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Massachusetts to Milwaukee flights
Consider these flights traveling from Massachusetts to Milwaukee.
Top 5 airlines flying from Massachusetts to Milwaukee
Discover the top 5 airlines that operate flights from Massachusetts 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 October 20, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$117 | Average$275 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$123 | Average$394 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$196 | Average$395 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$206 | Average$326 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$207 | Average$331 | FlexibilityNo cancel fee | On-time63% |