Round-trip from | $150 (Frontier) |
---|---|
One-way from | $79 (Southwest) |
Fly from
Fly to
Route
Depart
Return
Price
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Thu 3/13
6:00 am-7:35 pm
1 stop14h 35m
Chicago Midway
Sat 3/15
12:49 pm-12:34 am
1 stop10h 45m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Tue 1/14
6:00 am-1:34 pm
1 stop8h 34m
Chicago O'Hare Intl
Fri 1/17
10:02 pm-12:27 am
1 stop25h 25m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 1/16
6:00 am-2:32 pm
1 stop9h 32m
Chicago O'Hare Intl
Thu 1/23
4:41 pm-12:39 am
1 stop6h 58m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Fri 1/31
6:10 am-8:14 am
Nonstop3h 04m
Chicago O'Hare Intl
Wed 2/5
7:00 am-10:15 am
Nonstop2h 15m
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Thu 1/23
8:10 am-10:05 am
Nonstop2h 55m
Chicago Midway
Sun 1/26
8:40 am-11:55 am
Nonstop2h 15m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 1/23
2:52 pm-4:52 pm
Nonstop3h 00m
Chicago O'Hare Intl
Sun 1/26
12:30 pm-3:49 pm
Nonstop2h 19m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sat 2/22
10:03 am-11:58 pm
1 stop14h 55m
Chicago O'Hare Intl
Wed 2/26
3:14 pm-11:47 pm
1 stop7h 33m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sun 1/12
6:00 am-8:03 am
Nonstop3h 03m
Chicago O'Hare Intl
Sun 1/12
4:15 pm-7:38 pm
Nonstop2h 23m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 1/9
8:20 pm-10:23 pm
Nonstop3h 03m
Chicago O'Hare Intl
Sat 1/18
7:10 am-10:47 am
Nonstop2h 37m
WorcesterChicago
ORH - ORD
ORHORD
Worcester
Thu 1/23
2:32 pm-10:47 am
1 stop21h 15m
Chicago O'Hare Intl
Sun 1/26
4:22 pm-2:02 pm
1 stop20h 40m
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 $317). 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 Friday (56 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (14 on average).
In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.
If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).
Boarding
Crew
Comfort
Food
Overall
Entertainment
Reviews
We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.
Boarding
Crew
Comfort
Food
Overall
Entertainment
Reviews
We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.
Boarding
Crew
Comfort
Food
Overall
Entertainment
Reviews
We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.
Boarding
Crew
Comfort
Food
Overall
Entertainment
Reviews
We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.
Boarding
Crew
Comfort
Food
Overall
Entertainment
Reviews
We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.
Boarding
Crew
Comfort
Food
Overall
Entertainment
Reviews
We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.
Airline | Cheapest | Average | Flexibility | On-time |
---|---|---|---|---|
Spirit Airlines | Cheapest$39 | Average$105 | FlexibilityNo cancel fee | On-time65% |
JetBlue | Cheapest$81 | Average$232 | FlexibilityNo cancel fee | On-time62% |
Delta | Cheapest$93 | Average$357 | FlexibilityNo cancel fee | On-timeN/A |
Frontier | Cheapest$98 | Average$144 | FlexibilityNo cancel fee | On-time62% |
American Airlines | Cheapest$137 | Average$266 | FlexibilityNo cancel fee | On-time71% |
United Airlines | Cheapest$147 | Average$318 | FlexibilityNo cancel fee | On-time69% |
Southwest | Cheapest$148 | Average$294 | FlexibilityNo cancel fee | On-time63% |