
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $182 (Southwest) |
One-way from | $96 (Southwest) |
Popular in | May |
Cheapest in | September |
Average price | $247 |
Good round-trip deal | $256 or less |
Good one-way deal | $174 or less |
Fly from
Fly to
Route
Depart
Return
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Fri 7/3
6:45 pm-8:35 pm
Nonstop2h 50m
Chicago Midway
Mon 7/6
7:35 pm-10:55 pm
Nonstop2h 20m
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Mon 6/29
5:25 am-7:00 am
Nonstop2h 35m
Chicago Midway
Tue 7/7
2:40 pm-6:00 pm
Nonstop2h 20m
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Tue 7/7
5:35 am-7:10 am
Nonstop2h 35m
Chicago Midway
Tue 7/14
2:35 pm-10:45 pm
1 stop7h 10m
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Wed 7/15
11:35 am-5:00 pm
2 stops6h 25m
Chicago Midway
Sat 7/18
5:45 pm-9:10 pm
Nonstop2h 25m
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Sat 7/4
7:00 am-5:00 pm
2 stops11h 00m
Chicago Midway
Sun 7/5
5:15 am-8:25 am
Nonstop2h 10m
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Sat 7/25
5:20 am-6:55 am
Nonstop2h 35m
Chicago Midway
Tue 7/28
6:05 pm-9:25 pm
Nonstop2h 20m
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Wed 7/1
5:35 am-7:10 am
Nonstop2h 35m
Chicago Midway
Tue 7/7
8:40 am-5:05 pm
1 stop7h 25m
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Wed 8/26
8:15 am-1:30 pm
2 stops6h 15m
Chicago Midway
Sun 8/30
7:30 am-2:00 pm
1 stop5h 30m
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Tue 7/28
11:35 am-5:00 pm
2 stops6h 25m
Chicago Midway
Fri 7/31
7:35 pm-10:55 pm
Nonstop2h 20m
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Fri 10/16
12:50 pm-8:40 pm
2 stops8h 50m
Chicago Midway
Sun 10/18
8:25 am-11:55 am
Nonstop2h 30m
Currently, October is the cheapest month in which you can book a flight from Massachusetts to Chicago Midway Airport (average of $67). Flying from Massachusetts to Chicago Midway Airport in June is currently the most expensive (average of $157). 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.
Unlike in the morning, when flights are generally more expensive, you can save up to 25% on flights from Massachusetts to Chicago Midway Airport by exploring options for tickets in the evening.
The best time to book flights from Massachusetts to Chicago Midway Airport is 84 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
Travelers seeking maximum savings on their Massachusetts to Chicago Midway Airport flight should consider departing on Thursday evenings when fares are most often at their lowest. Saturday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$88 | Average$385 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$117 | Average$183 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$129 | Average$279 | FlexibilityNo cancel fee | On-time63% |