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Cheap flights from Wisconsin to Massachusetts from $55

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 8/20. 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

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Find the cheapest flights from Wisconsin to Massachusetts

Cheap round-trip flights

Spirit Airlines Logo
11:36 am - 11:49 pmORD-BOS
11h 13m1 stop
Spirit Airlines Logo
6:05 am - 7:07 pmBOS-ORD
14h 02m1 stop
$112Spirit Airlines
Find Deal
mié., ago. 27 - mié., sep. 3
United Airlines Logo
7:30 am - 11:01 amORD-BOS
2h 31mnonstop
United Airlines Logo
4:27 pm - 6:21 pmBOS-ORD
2h 54mnonstop
$117United Airlines
Find Deal
mié., sep. 3 - mié., sep. 3
American Airlines Logo
7:10 pm - 10:40 pmORD-BOS
2h 30mnonstop
American Airlines Logo
8:35 am - 10:32 amBOS-ORD
2h 57mnonstop
$120American Airlines
Find Deal
mié., sep. 3 - jue., sep. 4
American Airlines Logo
8:25 pm - 11:53 pmORD-BOS
2h 28mnonstop
American Airlines Logo
7:01 am - 9:05 amBOS-ORD
3h 04mnonstop
$128American Airlines
Find Deal
jue., sep. 4 - dom., sep. 7
JetBlue Logo
11:30 am - 2:46 pmORD-BOS
2h 16mnonstop
JetBlue Logo
4:55 pm - 7:05 pmBOS-ORD
3h 10mnonstop
$132JetBlue
Find Deal
mar., oct. 28 - mar., oct. 28
JetBlue Logo
7:50 pm - 11:25 pmORD-BOS
2h 35mnonstop
JetBlue Logo
7:00 am - 8:56 amBOS-ORD
2h 56mnonstop
$137JetBlue
Find Deal
vie., sep. 19 - lun., sep. 22
Southwest Logo
1:50 pm - 10:15 pmORD-BOS
7h 25m1 stop
Southwest Logo
5:40 am - 11:50 amBOS-ORD
7h 10m1 stop
$146Southwest
Find Deal
jue., sep. 4 - mié., sep. 10
Delta Logo
10:15 am - 1:48 pmORD-BOS
2h 33mnonstop
Delta Logo
7:55 pm - 9:56 pmBOS-ORD
3h 01mnonstop
$147Delta
Find Deal
jue., sep. 4 - mié., sep. 10
Delta Logo
7:25 am - 10:55 amORD-BOS
2h 30mnonstop
Delta Logo
7:20 am - 9:22 amBOS-ORD
3h 02mnonstop
$150Delta
Find Deal
mar., sep. 30 - mié., oct. 8
Southwest Logo
2:55 pm - 10:35 pmORD-BOS
6h 40m1 stop
Southwest Logo
5:15 am - 11:50 amBOS-ORD
7h 35m1 stop
$157Southwest
Find Deal
vie., sep. 12 - dom., sep. 14

Spirit Airlines flights from Wisconsin to Massachusetts

Our best Spirit Airlines deals on Wisconsin to Massachusetts flight tickets
Spirit Airlines
Aug 27
ORD11:36 amChicago O'Hare Intl
11h 13m
1 stop
BOS11:49 pmBoston Logan Intl
Sep 3
BOS6:05 amBoston Logan Intl
14h 02m
1 stop
ORD7:07 pmChicago O'Hare Intl
$112
Find similar
Spirit Airlines
Aug 19
ORD8:12 pmChicago O'Hare Intl
14h 06m
1 stop
BOS11:18 amBoston Logan Intl
Aug 20
BOS3:37 pmBoston Logan Intl
7h 45m
1 stop
ORD10:22 pmChicago O'Hare Intl
$121
Find similar
Spirit Airlines
Aug 26
ORD8:12 pmChicago O'Hare Intl
14h 06m
1 stop
BOS11:18 amBoston Logan Intl
Aug 27
BOS3:37 pmBoston Logan Intl
7h 45m
1 stop
ORD10:22 pmChicago O'Hare Intl
$124
Find similar

Delta flights from Wisconsin to Massachusetts

Our best Delta deals on Wisconsin to Massachusetts flight tickets
Delta
Sep 4
ORD10:15 amChicago O'Hare Intl
2h 33m
BOS1:48 pmBoston Logan Intl
Sep 10
BOS7:55 pmBoston Logan Intl
3h 01m
ORD9:56 pmChicago O'Hare Intl
$147
Find similar
Delta
Sep 30
ORD7:25 amChicago O'Hare Intl
2h 30m
BOS10:55 amBoston Logan Intl
Oct 8
BOS7:20 amBoston Logan Intl
3h 02m
ORD9:22 amChicago O'Hare Intl
$150
Find similar
Delta
Aug 19
ORD7:20 pmChicago O'Hare Intl
2h 38m
BOS10:58 pmBoston Logan Intl
Aug 23
BOS7:20 amBoston Logan Intl
2h 55m
ORD9:15 amChicago O'Hare Intl
$160
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 julio 31, 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

mié. 8/27

11:36 am-11:49 pm

1 stop11h 13m

Boston Logan Intl

mié. 9/3

6:05 am-7:07 pm

1 stop14h 02m

$112

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

mié. 9/3

7:30 am-11:01 am

Nonstop2h 31m

Boston Logan Intl

mié. 9/3

4:27 pm-6:21 pm

Nonstop2h 54m

$117

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

mié. 9/3

7:10 pm-10:40 pm

Nonstop2h 30m

Boston Logan Intl

jue. 9/4

8:35 am-10:32 am

Nonstop2h 57m

$120

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

jue. 9/4

8:25 pm-11:53 pm

Nonstop2h 28m

Boston Logan Intl

dom. 9/7

7:01 am-9:05 am

Nonstop3h 04m

$128

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

mar. 10/28

11:30 am-2:46 pm

Nonstop2h 16m

Boston Logan Intl

mar. 10/28

4:55 pm-7:05 pm

Nonstop3h 10m

$132

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

vie. 9/19

7:50 pm-11:25 pm

Nonstop2h 35m

Boston Logan Intl

lun. 9/22

7:00 am-8:56 am

Nonstop2h 56m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

jue. 9/4

1:50 pm-10:15 pm

1 stop7h 25m

Boston Logan Intl

mié. 9/10

5:40 am-11:50 am

1 stop7h 10m

$146

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

jue. 9/4

10:15 am-1:48 pm

Nonstop2h 33m

Boston Logan Intl

mié. 9/10

7:55 pm-9:56 pm

Nonstop3h 01m

$147

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

mar. 9/30

7:25 am-10:55 am

Nonstop2h 30m

Boston Logan Intl

mié. 10/8

7:20 am-9:22 am

Nonstop3h 02m

$150

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

vie. 9/12

2:55 pm-10:35 pm

1 stop6h 40m

Boston Logan Intl

dom. 9/14

5:15 am-11:50 am

1 stop7h 35m

$157

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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, May 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 $258. If you aren’t able to travel to Massachusetts during the month of May, then flying in September is also cheap. Prices for this month can be found on momondo for an average of $266.

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 $300. 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 $479.

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 $262. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are $438 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 $318 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 $245 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

$55

Fastest flight time

2h 02m

Direct flights

Every day

Airports in Massachusetts

3 airports
The best one-way flight to Massachusetts from Wisconsin in the past 72 hours is $55. The best round-trip flight deal from Wisconsin to Massachusetts found on momondo in the last 72 hours is $112.
The fastest flight from Wisconsin to Massachusetts takes 2h 02m
Direct flights go from Wisconsin to Massachusetts every day.
There are 3 airports near Massachusetts: Boston Logan Intl (BOS), 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 $134Free CancellationRating
7.2
2,914 reviews
Search JetBlue flights
Spirit AirlinesPriceFrom $164Free CancellationRating
6.3
8,049 reviews
Search Spirit Airlines flights
DeltaPriceFrom $166Free CancellationRating
8.0
7,981 reviews
Search Delta flights
United AirlinesPriceFrom $176Free CancellationRating
7.4
8,900 reviews
Search United Airlines flights
American AirlinesPriceFrom $176Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
SouthwestPriceFrom $186Free CancellationRating
8.0
4,246 reviews
Search Southwest 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.
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mar. 8/5
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