Latest deals
Insights
FAQs
Reviews
Price Alerts

Cheap flights from Wisconsin to Massachusetts from $69

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Wisconsin to Massachusetts departing on 10/6. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Wisconsin to Massachusetts

Cheap round-trip flights

Delta Logo
7:05 am - 10:29 amORD-BOS
2h 24mnonstop
Delta Logo
7:30 pm - 9:19 pmBOS-ORD
2h 49mnonstop
$127Delta
Find Deal
jue., oct. 30 - mié., nov. 5
JetBlue Logo
10:08 am - 1:37 pmORD-BOS
2h 29mnonstop
JetBlue Logo
4:05 pm - 6:18 pmBOS-ORD
3h 13mnonstop
$130JetBlue
Find Deal
mar., oct. 21 - mar., oct. 21
United Airlines Logo
9:25 pm - 12:45 amORD-BOS
2h 20mnonstop
United Airlines Logo
6:00 am - 8:00 amBOS-ORD
3h 00mnonstop
$131United Airlines
Find Deal
vie., nov. 7 - dom., nov. 9
United Airlines Logo
6:14 pm - 9:45 pmORD-BOS
2h 31mnonstop
United Airlines Logo
6:00 am - 7:56 amBOS-ORD
2h 56mnonstop
$133United Airlines
Find Deal
sáb., oct. 11 - sáb., oct. 18
Delta Logo
7:10 am - 10:37 amORD-BOS
2h 27mnonstop
Delta Logo
12:50 pm - 2:50 pmBOS-ORD
3h 00mnonstop
$137Delta
Find Deal
jue., dic. 4 - lun., dic. 8
American Airlines Logo
8:11 pm - 11:44 pmORD-BOS
2h 33mnonstop
American Airlines Logo
6:45 am - 8:52 amBOS-ORD
3h 07mnonstop
$141American Airlines
Find Deal
sáb., nov. 15 - dom., nov. 23
Southwest Logo
1:50 pm - 9:10 pmORD-BOS
6h 20m1 stop
Southwest Logo
7:50 am - 5:55 pmBOS-ORD
11h 05m2 stops
$142Southwest
Find Deal
mar., oct. 21 - mar., oct. 28
American Airlines Logo
6:05 am - 9:32 amORD-BOS
2h 27mnonstop
American Airlines Logo
3:51 pm - 5:52 pmBOS-ORD
3h 01mnonstop
$145American Airlines
Find Deal
dom., oct. 26 - mar., oct. 28
JetBlue Logo
11:20 am - 2:44 pmORD-BOS
2h 24mnonstop
JetBlue Logo
5:35 pm - 7:50 pmBOS-ORD
3h 15mnonstop
$147JetBlue
Find Deal
mié., nov. 19 - sáb., nov. 22
Southwest Logo
4:50 pm - 10:40 pmMKE-BOS
4h 50m1 stop
Southwest Logo
5:00 am - 11:30 amBOS-MKE
7h 30m2 stops
$182Southwest
Find Deal
mié., oct. 22 - mié., oct. 29

United Airlines flights from Wisconsin to Massachusetts

Our best United Airlines deals on Wisconsin to Massachusetts flight tickets
United Airlines
Nov 7
ORD9:25 pmChicago O'Hare Intl
2h 20m
BOS12:45 amBoston Logan Intl
Nov 9
BOS6:00 amBoston Logan Intl
3h 00m
ORD8:00 amChicago O'Hare Intl
$131
Find similar
United Airlines
Oct 11
ORD6:14 pmChicago O'Hare Intl
2h 31m
BOS9:45 pmBoston Logan Intl
Oct 18
BOS6:00 amBoston Logan Intl
2h 56m
ORD7:56 amChicago O'Hare Intl
$133
Find similar
United Airlines
Oct 12
ORD6:30 amChicago O'Hare Intl
2h 26m
BOS9:56 amBoston Logan Intl
Oct 18
BOS6:00 amBoston Logan Intl
2h 56m
ORD7:56 amChicago O'Hare Intl
$134
Find similar

Spirit Airlines flights from Wisconsin to Massachusetts

Our best Spirit Airlines deals on Wisconsin to Massachusetts flight tickets
Spirit Airlines
Oct 28
ORD6:00 amChicago O'Hare Intl
6h 20m
1 stop
BOS1:20 pmBoston Logan Intl
Oct 29
BOS3:00 pmBoston Logan Intl
11h 03m
1 stop
ORD1:03 amChicago O'Hare Intl
$139
Find similar
Spirit Airlines
Nov 11
ORD10:49 amChicago O'Hare Intl
12h 51m
1 stop
BOS12:40 amBoston Logan Intl
Nov 12
BOS5:45 amBoston Logan Intl
13h 38m
1 stop
ORD6:23 pmChicago O'Hare Intl
$140
Find similar
Spirit Airlines
Oct 28
ORD6:00 amChicago O'Hare Intl
6h 20m
1 stop
BOS1:20 pmBoston Logan Intl
Nov 11
BOS5:45 amBoston Logan Intl
13h 38m
1 stop
ORD6:23 pmChicago O'Hare Intl
$146
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Wisconsin to Massachusetts 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, momondo users made 832,500 searches. Data last updated septiembre 25, 2025.
Use the filters below to find and compare flights from Wisconsin to Massachusetts that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

jue. 10/30

7:05 am-10:29 am

Nonstop2h 24m

Boston Logan Intl

mié. 11/5

7:30 pm-9:19 pm

Nonstop2h 49m

$127

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

mar. 10/21

10:08 am-1:37 pm

Nonstop2h 29m

Boston Logan Intl

mar. 10/21

4:05 pm-6:18 pm

Nonstop3h 13m

$130

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

vie. 11/7

9:25 pm-12:45 am

Nonstop2h 20m

Boston Logan Intl

dom. 11/9

6:00 am-8:00 am

Nonstop3h 00m

$131

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

sáb. 10/11

6:14 pm-9:45 pm

Nonstop2h 31m

Boston Logan Intl

sáb. 10/18

6:00 am-7:56 am

Nonstop2h 56m

$133

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

jue. 12/4

7:10 am-10:37 am

Nonstop2h 27m

Boston Logan Intl

lun. 12/8

12:50 pm-2:50 pm

Nonstop3h 00m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

sáb. 11/15

8:11 pm-11:44 pm

Nonstop2h 33m

Boston Logan Intl

dom. 11/23

6:45 am-8:52 am

Nonstop3h 07m

$141

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

mar. 10/21

1:50 pm-9:10 pm

1 stop6h 20m

Boston Logan Intl

mar. 10/28

7:50 am-5:55 pm

2 stops11h 05m

$142

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

dom. 10/26

6:05 am-9:32 am

Nonstop2h 27m

Boston Logan Intl

mar. 10/28

3:51 pm-5:52 pm

Nonstop3h 01m

$145

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

mié. 11/19

11:20 am-2:44 pm

Nonstop2h 24m

Boston Logan Intl

sáb. 11/22

5:35 pm-7:50 pm

Nonstop3h 15m

$147

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

mié. 10/22

4:50 pm-10:40 pm

1 stop4h 50m

Boston Logan Intl

mié. 10/29

5:00 am-11:30 am

2 stops7h 30m

$182

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

See travel insights to Massachusetts from

How to get the cheapest flight ticket from Wisconsin to Massachusetts

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Massachusetts?

In general, August is the cheapest month to fly from Wisconsin to Massachusetts. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $251. If you aren’t able to travel to Massachusetts during the month of August, then flying in May is also cheap. Prices for this month can be found on momondo for an average of $258.

What is the cheapest day to depart on your flight to Massachusetts?

According to our data, Saturday is the cheapest day to fly to Massachusetts from Wisconsin. The lowest ticket price found for a Saturday departure recently was $310. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Sunday is the most expensive day to depart from Wisconsin because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $480.

What is the cheapest time of day to depart on your flight to Massachusetts?

Our data shows that the cheapest Wisconsin to Massachusetts flights are usually those with departure times in the evening. Our users have found flights to Massachusetts in the evening for as low as $252. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are $473 on average. Flights to Massachusetts from Wisconsin in the morning are generally more expensive because this time of day is more convenient for travelers’ schedules.

What is the cheapest Wisconsin to Massachusetts flight route?

Fly from Milwaukee-Mitchell to Boston Logan Intl for the best Wisconsin - Massachusetts flight prices

How far in advance should I book a flight to Massachusetts?

You are more likely to see cheaper flights to Massachusetts from Wisconsin when booking weeks ahead of your departure date. In general, you can expect to find flights to Massachusetts for around $320 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Massachusetts from Wisconsin for as low as $234 on momondo.

What cabin class options are available on Wisconsin to Massachusetts flights?

There are 4 cabin classes available to choose from on Wisconsin to Massachusetts flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Wisconsin to Massachusetts flights?

No. A direct flight is the cheapest option for a flight between Wisconsin to Massachusetts.

Cheap Wisconsin to Massachusetts flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Wisconsin to Massachusetts

Best Price Found

$208

Fastest flight time

2h 01m

Direct flights

Every day

Airports in Massachusetts

2 airports
The best one-way flight to Massachusetts from Wisconsin in the past 72 hours is $208. The best round-trip flight deal from Wisconsin to Massachusetts found on momondo in the last 72 hours is $203.
The fastest flight from Wisconsin to Massachusetts takes 2h 01m
Direct flights go from Wisconsin to Massachusetts every day.
There are 2 airports near Massachusetts: Albany Intl (ALB), Hartford Bradley Intl (BDL)
Search flight deals

  • When did momondo last update prices for flights from Wisconsin to Massachusetts?

    Prices for flights from Wisconsin to Massachusetts are refreshed on a daily basis.

  • How many operators does momondo search for flights from Wisconsin to Massachusetts?

  • How old do you have to be to fly from Wisconsin to Massachusetts?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Wisconsin to Massachusetts.

  • What documentation or ID do you need to fly to Massachusetts?

    The necessary travel and health documents for your Massachusetts trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Wisconsin to Massachusetts?

Best airlines flying from Wisconsin to Massachusetts

Compare and see reviews for airlines that fly from Wisconsin to Massachusetts with momondo
Airline
Rating
Free Cancellation
Price
JetBluePriceFrom $118Free CancellationRating
7.2
2,914 reviews
Search JetBlue flights
DeltaPriceFrom $158Free CancellationRating
7.9
7,973 reviews
Search Delta flights
Spirit AirlinesPriceFrom $164Free CancellationRating
6.3
8,042 reviews
Search Spirit Airlines flights
American AirlinesPriceFrom $180Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
SouthwestPriceFrom $181Free CancellationRating
8.0
4,246 reviews
Search Southwest flights
United AirlinesPriceFrom $186Free CancellationRating
7.4
8,928 reviews
Search United Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Wisconsin to Massachusetts?

It is quick and easy to find Wisconsin to Massachusetts flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Massachusetts that suits you.

Can I find flights from Wisconsin to Massachusetts with flexible booking policies on momondo?

momondo does allow users to show only those flights to Massachusetts from Wisconsin which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Wisconsin to Massachusetts?

Once all potential Wisconsin to Massachusetts flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Wisconsin to Massachusetts right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Wisconsin to Massachusetts now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Massachusetts and let you know when they change.

An easier way to manage your Massachusetts trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
sáb. 10/25
sáb. 11/1
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Massachusetts

Popular cities in Massachusetts

Popular flights according to clicks in the last 7 days on momondo
Flights to New Yorkfrom $50
Flights to Los Angelesfrom $49
Flights to Miamifrom $52
Flights to Chicagofrom $65
Flights to Orlandofrom $57
Flights to Las Vegasfrom $47
Flights to San Franciscofrom $59
Flights to Washington, D.C.from $60
Flights to Bostonfrom $68
Flights to Atlantafrom $51
Flights to Dallasfrom $60
Flights to Seattlefrom $86