
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $159 (Expedia) |
One-way from | $70 (Frontier) |
Popular in | November |
Cheapest in | September |
Average price | $277 |
Good round-trip deal | $154 or less |
Good one-way deal | $128 or less |
Fly from
Fly to
Route
Depart
Return
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
ke 5/20
7:35 am-9:27 am
Nonstop2h 52m
Chicago O'Hare Intl
to 5/28
10:25 am-1:49 pm
Nonstop2h 24m
BostonMilwaukee
BOS - MKE
BOSMKE
Boston Logan Intl
la 5/16
2:51 pm-4:29 pm
Nonstop2h 38m
Milwaukee-Mitchell
ti 5/19
4:58 pm-8:13 pm
Nonstop2h 15m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
ma 5/25
6:00 am-7:58 am
Nonstop2h 58m
Chicago O'Hare Intl
to 5/28
6:00 am-11:16 am
1 stop4h 16m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
ti 6/16
5:25 am-1:15 pm
2 stops8h 50m
Chicago O'Hare Intl
ke 6/17
2:40 pm-11:20 pm
2 stops7h 40m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
su 6/7
7:30 am-9:28 am
Nonstop2h 58m
Chicago O'Hare Intl
pe 6/12
7:25 pm-11:02 pm
Nonstop2h 37m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
su 5/31
5:45 am-9:36 am
1 stop4h 51m
Chicago O'Hare Intl
ma 6/1
9:26 pm-12:59 am
Nonstop2h 33m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
ke 7/1
5:45 am-9:36 am
1 stop4h 51m
Chicago O'Hare Intl
ma 7/6
9:35 pm-1:08 am
Nonstop2h 33m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
pe 5/22
6:00 am-8:00 am
Nonstop3h 00m
Chicago O'Hare Intl
to 5/28
8:30 pm-11:59 pm
Nonstop2h 29m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
pe 6/26
7:30 am-9:28 am
Nonstop2h 58m
Chicago O'Hare Intl
ma 6/29
7:10 am-10:46 am
Nonstop2h 36m
BostonMilwaukee
BOS - MKE
BOSMKE
Boston Logan Intl
la 5/23
6:40 pm-10:34 pm
1 stop4h 54m
Milwaukee-Mitchell
ti 5/26
7:15 pm-1:14 am
1 stop4h 59m
Booking 89 days in advance of your planned departure date is, on average, the best time to get cheap flights from Massachusetts to Wisconsin. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
Currently, August is the cheapest month in which you can book a flight from Massachusetts to Wisconsin (average of $78). Flying from Massachusetts to Wisconsin in March is currently the most expensive (average of $207). 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.
When flying from Massachusetts to Wisconsin, the time of day you fly usually plays a role in the price. Save by searching for a flight at noon, which can drop the price by up to 34% versus a flight in the morning.
Travelers seeking maximum savings on their Massachusetts to Wisconsin flight should consider departing on Wednesday at noon when fares are most often at their lowest. Wednesday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
Crew
Comfort
Overall
Food
Entertainment
Boarding
Reviews
Dominic,Mar 2026
MCO - SMF
Crew
Comfort
Overall
Food
Entertainment
Boarding
Reviews
Dominic,Mar 2026
MCO - SMF
Crew
Comfort
Overall
Food
Entertainment
Boarding
Reviews
Dominic,Mar 2026
MCO - SMF
Crew
Comfort
Overall
Food
Entertainment
Boarding
Reviews
Dominic,Mar 2026
MCO - SMF
Crew
Comfort
Overall
Food
Entertainment
Boarding
Reviews
Dominic,Mar 2026
MCO - SMF
Crew
Comfort
Overall
Food
Entertainment
Boarding
Reviews
Dominic,Mar 2026
MCO - SMF
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$98 | Average$268 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$145 | Average$418 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$176 | Average$271 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$176 | Average$459 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$196 | Average$443 | FlexibilityNo cancel fee | On-time71% |