Round-trip from | $137 (Southwest) |
---|---|
One-way from | $69 (Southwest) |
Popular in | March |
Cheapest in | September |
Average price | $223 |
Good round-trip deal | $137 or less |
Good one-way deal | $123 or less |
Fly from
Fly to
Route
Depart
Return
Price
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Tue 7/15
7:20 am-9:00 am
Nonstop2h 40m
Chicago Midway
Thu 7/17
8:05 am-11:20 am
Nonstop2h 15m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 7/23
7:20 am-9:18 am
Nonstop2h 58m
Chicago O'Hare Intl
Mon 7/28
7:00 am-10:31 am
Nonstop2h 31m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 7/30
8:39 pm-8:55 am
1 stop13h 16m
Chicago O'Hare Intl
Tue 8/5
5:05 am-7:34 pm
1 stop13h 29m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Tue 7/15
2:55 pm-5:02 pm
Nonstop3h 07m
Chicago O'Hare Intl
Thu 7/17
8:30 pm-12:14 am
Nonstop2h 44m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Tue 7/15
7:04 pm-11:41 pm
1 stop5h 37m
Chicago O'Hare Intl
Tue 7/22
3:48 pm-7:18 pm
Nonstop2h 30m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 7/17
6:00 am-2:04 pm
1 stop9h 04m
Chicago O'Hare Intl
Sat 7/19
12:20 pm-12:39 am
1 stop11h 19m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sun 8/24
9:20 am-6:41 pm
1 stop10h 21m
Chicago O'Hare Intl
Wed 8/27
11:36 am-11:49 pm
1 stop11h 13m
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Sat 8/16
9:40 am-8:22 pm
1 stop11h 42m
Chicago Midway
Sun 8/17
3:58 pm-12:38 am
1 stop7h 40m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Tue 7/15
5:45 am-11:50 am
1 stop7h 05m
Chicago O'Hare Intl
Sat 7/19
1:30 pm-9:05 pm
1 stop6h 35m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sat 7/26
7:00 am-8:55 am
Nonstop2h 55m
Chicago O'Hare Intl
Tue 7/29
8:40 am-12:04 pm
Nonstop2h 24m
Currently, August is the cheapest month in which you can book a flight from Massachusetts to Chicago (average of $245). Flying from Massachusetts to Chicago in March is currently the most expensive (average of $321). 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.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Massachusetts to Chicago as you normally would.
The most flights from USMA to CHI are scheduled on a Thursday (80 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (5 on average).
Overall
Comfort
Food
Crew
Boarding
Entertainment
Reviews
John,May 2025
PVD - BNA
Overall
Comfort
Food
Crew
Boarding
Entertainment
Reviews
John,May 2025
PVD - BNA
Overall
Comfort
Food
Crew
Boarding
Entertainment
Reviews
John,May 2025
PVD - BNA
Overall
Comfort
Food
Crew
Boarding
Entertainment
Reviews
John,May 2025
PVD - BNA
Overall
Comfort
Food
Crew
Boarding
Entertainment
Reviews
John,May 2025
PVD - BNA
Overall
Comfort
Food
Crew
Boarding
Entertainment
Reviews
John,May 2025
PVD - BNA
Airline | Cheapest | Average | Flexibility | On-time |
---|---|---|---|---|
Cheapest$41 | Average$111 | FlexibilityNo cancel fee | On-time65% | |
Cheapest$78 | Average$203 | FlexibilityNo cancel fee | On-time62% | |
Cheapest$94 | Average$312 | FlexibilityNo cancel fee | On-timeN/A | |
Cheapest$97 | Average$233 | FlexibilityNo cancel fee | On-time69% | |
Cheapest$100 | Average$117 | FlexibilityNo cancel fee | On-time62% | |
Cheapest$124 | Average$303 | FlexibilityNo cancel fee | On-time63% | |
Cheapest$136 | Average$254 | FlexibilityNo cancel fee | On-time71% |