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Cheap flights from Massachusetts to Wisconsin from $40

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Massachusetts to Wisconsin departing on 9/7. 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 Massachusetts to Wisconsin

Cheap round-trip flights

JetBlue Logo
7:00 am - 8:56 amBOS-ORD
2h 56mnonstop
JetBlue Logo
9:51 am - 1:20 pmORD-BOS
2h 29mnonstop
$80JetBlue
Find Deal
Thu, Sep 4 - Tue, Sep 9
JetBlue Logo
7:00 am - 8:56 amBOS-ORD
2h 56mnonstop
JetBlue Logo
9:51 am - 1:20 pmORD-BOS
2h 29mnonstop
$81JetBlue
Find Deal
Sat, Sep 20 - Sat, Sep 27
Southwest Logo
7:30 am - 12:45 pmBOS-ORD
6h 15m1 stop
Southwest Logo
1:50 pm - 10:15 pmORD-BOS
7h 25m1 stop
$87Southwest
Find Deal
Thu, Sep 4 - Mon, Sep 8
American Airlines Logo
2:45 pm - 4:49 pmBOS-ORD
3h 04mnonstop
American Airlines Logo
6:05 am - 9:32 amORD-BOS
2h 27mnonstop
$94American Airlines
Find Deal
Thu, Sep 4 - Thu, Sep 11
Southwest Logo
10:45 am - 4:25 pmBOS-ORD
6h 40m1 stop
Southwest Logo
1:50 pm - 10:15 pmORD-BOS
7h 25m1 stop
$96Southwest
Find Deal
Fri, Sep 5 - Mon, Sep 8
American Airlines Logo
7:19 pm - 9:25 pmBOS-ORD
3h 06mnonstop
American Airlines Logo
3:08 pm - 6:29 pmORD-BOS
2h 21mnonstop
$98American Airlines
Find Deal
Fri, Nov 14 - Mon, Nov 17
United Airlines Logo
6:16 pm - 8:10 pmBOS-ORD
2h 54mnonstop
United Airlines Logo
6:30 am - 9:56 amORD-BOS
2h 26mnonstop
$108United Airlines
Find Deal
Wed, Aug 20 - Sun, Aug 24
United Airlines Logo
8:47 pm - 10:35 pmBOS-ORD
2h 48mnonstop
United Airlines Logo
6:30 am - 9:56 amORD-BOS
2h 26mnonstop
$113United Airlines
Find Deal
Fri, Oct 17 - Sun, Oct 19
Delta Logo
7:55 pm - 9:54 pmBOS-ORD
2h 59mnonstop
Delta Logo
7:00 am - 10:29 amORD-BOS
2h 29mnonstop
$117Delta
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Fri, Aug 22 - Tue, Aug 26
Delta Logo
7:55 pm - 9:56 pmBOS-ORD
3h 01mnonstop
Delta Logo
7:20 pm - 10:59 pmORD-BOS
2h 39mnonstop
$119Delta
Find Deal
Thu, Sep 4 - Mon, Sep 8

Spirit Airlines flights from Massachusetts to Wisconsin

Our best Spirit Airlines deals on Massachusetts to Wisconsin flight tickets
Spirit Airlines
Sep 3
BOS6:05 amBoston Logan Intl
14h 02m
1 stop
ORD7:07 pmChicago O'Hare Intl
Sep 10
ORD11:57 amChicago O'Hare Intl
11h 00m
1 stop
BOS11:57 pmBoston Logan Intl
$112
Find similar
Spirit Airlines
Aug 26
BOS3:37 pmBoston Logan Intl
7h 45m
1 stop
ORD10:22 pmChicago O'Hare Intl
Sep 3
ORD11:36 amChicago O'Hare Intl
11h 13m
1 stop
BOS11:49 pmBoston Logan Intl
$121
Find similar
Spirit Airlines
Oct 31
BDL1:00 pmHartford Bradley Intl
5h 38m
1 stop
ORD5:38 pmChicago O'Hare Intl
Nov 2
ORD12:31 pmChicago O'Hare Intl
22h 24m
1 stop
BDL11:55 amHartford Bradley Intl
$123
Find similar

Frontier flights from Massachusetts to Wisconsin

Our best Frontier deals on Massachusetts to Wisconsin flight tickets
Frontier
Aug 22
BDL11:44 amHartford Bradley Intl
7h 57m
1 stop
ORD6:41 pmChicago O'Hare Intl
Aug 23
ORD7:46 pmChicago O'Hare Intl
13h 24m
1 stop
BDL10:10 amHartford Bradley Intl
$208
Find similar
Frontier
Aug 15
BDL8:44 pmHartford Bradley Intl
12h 23m
1 stop
ORD8:07 amChicago O'Hare Intl
Aug 17
ORD5:01 amChicago O'Hare Intl
5h 40m
1 stop
BDL11:41 amHartford Bradley Intl
$218
Find similar
Frontier
Aug 11
BDL8:53 pmHartford Bradley Intl
14h 21m
1 stop
ORD10:14 amChicago O'Hare Intl
Aug 21
ORD7:46 pmChicago O'Hare Intl
14h 03m
1 stop
BDL10:49 amHartford Bradley Intl
$225
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Massachusetts to Wisconsin 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 August 7, 2025.
Use the filters below to find and compare flights from Massachusetts to Wisconsin that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 9/4

7:00 am-8:56 am

Nonstop2h 56m

Chicago O'Hare Intl

Tue 9/9

9:51 am-1:20 pm

Nonstop2h 29m

$80

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 9/20

7:00 am-8:56 am

Nonstop2h 56m

Chicago O'Hare Intl

Sat 9/27

9:51 am-1:20 pm

Nonstop2h 29m

$81

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 9/4

7:30 am-12:45 pm

1 stop6h 15m

Chicago O'Hare Intl

Mon 9/8

1:50 pm-10:15 pm

1 stop7h 25m

$87

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 9/4

2:45 pm-4:49 pm

Nonstop3h 04m

Chicago O'Hare Intl

Thu 9/11

6:05 am-9:32 am

Nonstop2h 27m

$94

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 9/5

10:45 am-4:25 pm

1 stop6h 40m

Chicago O'Hare Intl

Mon 9/8

1:50 pm-10:15 pm

1 stop7h 25m

$96

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 11/14

7:19 pm-9:25 pm

Nonstop3h 06m

Chicago O'Hare Intl

Mon 11/17

3:08 pm-6:29 pm

Nonstop2h 21m

$98

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 8/20

6:16 pm-8:10 pm

Nonstop2h 54m

Chicago O'Hare Intl

Sun 8/24

6:30 am-9:56 am

Nonstop2h 26m

$108

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 10/17

8:47 pm-10:35 pm

Nonstop2h 48m

Chicago O'Hare Intl

Sun 10/19

6:30 am-9:56 am

Nonstop2h 26m

$113

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 8/22

7:55 pm-9:54 pm

Nonstop2h 59m

Chicago O'Hare Intl

Tue 8/26

7:00 am-10:29 am

Nonstop2h 29m

$117

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 9/4

7:55 pm-9:56 pm

Nonstop3h 01m

Chicago O'Hare Intl

Mon 9/8

7:20 pm-10:59 pm

Nonstop2h 39m

$119

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 Wisconsin from

How to get the cheapest flight ticket from Massachusetts to Wisconsin

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 Wisconsin?

If you aren’t able to travel during the month of August, then book flights to Wisconsin from Massachusetts during September instead. Flights to Wisconsin in September, while not as cheap as those in August, still average around $286.

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

The cheapest day to depart from Massachusetts to Wisconsin is on a Wednesday. Travelers who choose to depart for Wisconsin on a Wednesday will often find tickets for as low as $296. The most expensive day to fly to Wisconsin is Monday, with ticket prices averaging around $394.

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

Our most recent data shows that the best time of day to fly to Wisconsin is at noon. Flights from Massachusetts to Wisconsin during this time can be as low as $289. Flights in the evening are often more expensive with an average ticket price of $403.

What is the cheapest Massachusetts to Wisconsin flight route?

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

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

You are more likely to see cheaper flights to Wisconsin from Massachusetts when booking weeks ahead of your departure date. In general, you can expect to find flights to Wisconsin for around $339 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Wisconsin from Massachusetts for as low as $238 on momondo.

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

There are 4 cabin classes available to choose from on Massachusetts to Wisconsin 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 Massachusetts to Wisconsin flights?

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

Cheap Massachusetts to Wisconsin flight deals and tips

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

Best Price Found

$40

Fastest flight time

2h 23m

Direct flights

Every day

Airports in Wisconsin

3 airports
The best one-way flight to Wisconsin from Massachusetts in the past 72 hours is $40. The best round-trip flight deal from Massachusetts to Wisconsin found on momondo in the last 72 hours is $80.
The fastest flight from Massachusetts to Wisconsin takes 2h 23m
Direct flights go from Massachusetts to Wisconsin every day.
There are 3 airports near Wisconsin: Chicago O'Hare Intl (ORD), Milwaukee-Mitchell (MKE), Madison Truax Field (MSN)
Search flight deals

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

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

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

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

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Massachusetts to Wisconsin.

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

    The travel and health documents required for your trip to Wisconsin can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Wisconsin. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

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

Best airlines flying from Massachusetts to Wisconsin

Compare and see reviews for airlines that fly from Massachusetts to Wisconsin with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $112Free CancellationRating
6.3
8,055 reviews
Search Spirit Airlines flights
JetBluePriceFrom $135Free CancellationRating
7.2
2,915 reviews
Search JetBlue flights
SouthwestPriceFrom $176Free CancellationRating
8.0
4,247 reviews
Search Southwest flights
United AirlinesPriceFrom $186Free CancellationRating
7.4
8,917 reviews
Search United Airlines flights
American AirlinesPriceFrom $186Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
DeltaPriceFrom $195Free CancellationRating
8.0
7,985 reviews
Search Delta flights

Why use momondo?

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

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Wisconsin from Massachusetts.

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

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

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

Once you have performed a search for Massachusetts to Wisconsin flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

Price alerts on flights to Wisconsin from Massachusetts are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

An easier way to manage your Wisconsin 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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