
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $162 (Cheapflightsfares) |
One-way from | $83 (Super.com) |
Popular in | November |
Cheapest in | September |
Average price | $277 |
Good round-trip deal | $185 or less |
Good one-way deal | $128 or less |
Fly from
Fly to
Route
Depart
Return
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Tue 6/2
7:19 am-9:17 am
Nonstop2h 58m
Chicago O'Hare Intl
Wed 6/3
6:05 am-9:29 am
Nonstop2h 24m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Tue 6/2
7:19 am-9:17 am
Nonstop2h 58m
Chicago O'Hare Intl
Tue 6/9
9:41 pm-1:14 am
Nonstop2h 33m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sat 5/23
5:30 pm-7:33 pm
Nonstop3h 03m
Chicago O'Hare Intl
Sun 5/24
7:00 am-10:35 am
Nonstop2h 35m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Fri 5/29
6:00 am-7:58 am
Nonstop2h 58m
Chicago O'Hare Intl
Sat 5/30
7:45 pm-11:21 pm
Nonstop2h 36m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Fri 5/29
8:20 pm-10:20 pm
Nonstop3h 00m
Chicago O'Hare Intl
Tue 6/30
9:41 pm-1:14 am
Nonstop2h 33m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 6/10
6:40 pm-8:40 pm
Nonstop3h 00m
Chicago O'Hare Intl
Wed 6/17
6:00 am-11:16 am
1 stop4h 16m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Tue 6/2
6:00 am-8:00 am
Nonstop3h 00m
Chicago O'Hare Intl
Mon 6/8
8:30 pm-11:59 pm
Nonstop2h 29m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Mon 7/13
6:00 am-7:58 am
Nonstop2h 58m
Chicago O'Hare Intl
Wed 7/15
6:00 am-11:16 am
1 stop4h 16m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Fri 7/3
5:45 am-9:36 am
1 stop4h 51m
Chicago O'Hare Intl
Wed 7/8
7:45 pm-11:21 pm
Nonstop2h 36m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 6/10
5:45 am-9:36 am
1 stop4h 51m
Chicago O'Hare Intl
Sun 6/14
6:05 am-9:29 am
Nonstop2h 24m
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 19% 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.
Overall
Entertainment
Boarding
Food
Comfort
Crew
Reviews
Dominic,Mar 2026
MCO - SMF
Overall
Entertainment
Boarding
Food
Comfort
Crew
Reviews
Dominic,Mar 2026
MCO - SMF
Overall
Entertainment
Boarding
Food
Comfort
Crew
Reviews
Dominic,Mar 2026
MCO - SMF
Overall
Entertainment
Boarding
Food
Comfort
Crew
Reviews
Dominic,Mar 2026
MCO - SMF
Overall
Entertainment
Boarding
Food
Comfort
Crew
Reviews
Dominic,Mar 2026
MCO - SMF
Overall
Entertainment
Boarding
Food
Comfort
Crew
Reviews
Dominic,Mar 2026
MCO - SMF
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$98 | Average$267 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$144 | Average$428 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$176 | Average$272 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$176 | Average$456 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$196 | Average$442 | FlexibilityNo cancel fee | On-time71% |