
Most accurate provider | eDreams 3 stars |
|---|---|
Most trusted provider | eDreams 3 stars |
Round-trip from | $117 (Delta) |
One-way from | $47 (United Airlines) |
Popular in | April |
Cheapest in | September |
Average price | $252 |
Good round-trip deal | $131 or less |
Good one-way deal | $65 or less |
Fly from
Fly to
Route
Depart
Return
Price
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Fri 1/23
2:25 pm-5:54 pm
Nonstop2h 29m
Boston Logan Intl
Thu 1/29
7:30 am-9:41 am
Nonstop3h 11m
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Thu 12/25
6:15 pm-9:35 pm
Nonstop2h 20m
Boston Logan Intl
Fri 1/2
5:15 am-7:00 am
Nonstop2h 45m
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Fri 12/12
7:30 am-10:49 am
Nonstop2h 19m
Boston Logan Intl
Sun 12/14
6:00 am-8:00 am
Nonstop3h 00m
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Thu 1/8
6:15 am-2:05 pm
1 stop6h 50m
Boston Logan Intl
Mon 1/12
7:55 pm-10:01 pm
Nonstop3h 06m
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Tue 2/3
2:25 pm-5:54 pm
Nonstop2h 29m
Boston Logan Intl
Mon 2/9
6:35 pm-11:56 pm
1 stop6h 21m
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Fri 1/30
2:25 pm-5:54 pm
Nonstop2h 29m
Boston Logan Intl
Sat 1/31
5:29 am-9:41 am
1 stop5h 12m
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Tue 2/17
10:11 am-1:35 pm
Nonstop2h 24m
Boston Logan Intl
Tue 2/24
3:50 pm-5:53 pm
Nonstop3h 03m
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Thu 1/22
10:29 am-3:53 pm
1 stop4h 24m
Boston Logan Intl
Sat 1/31
5:15 pm-7:26 pm
Nonstop3h 11m
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Tue 1/20
10:45 am-4:23 pm
1 stop4h 38m
Boston Logan Intl
Wed 1/28
4:10 pm-6:19 pm
Nonstop3h 09m
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 1/21
10:29 am-3:53 pm
1 stop4h 24m
Boston Logan Intl
Tue 1/27
11:30 am-1:39 pm
Nonstop3h 09m
Currently, September is the cheapest month in which you can book a flight from Chicago to Massachusetts (average of $91). Flying from Chicago to Massachusetts in February is currently the most expensive (average of $138). 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.
One of the essential ways to save on airfare from Chicago to Massachusetts is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the evening could potentially save you up to 64% on airfare.
Travelers seeking maximum savings on their Chicago to Massachusetts flight should consider departing on Tuesday evenings when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
The most flights from CHI to USMA are scheduled on a Tuesday (54 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (23 on average).
Overall
Comfort
Food
Entertainment
Boarding
Crew
Reviews
William Drew,Nov 2025
SJC - HNL
Overall
Comfort
Food
Entertainment
Boarding
Crew
Reviews
William Drew,Nov 2025
SJC - HNL
Overall
Comfort
Food
Entertainment
Boarding
Crew
Reviews
William Drew,Nov 2025
SJC - HNL
Overall
Comfort
Food
Entertainment
Boarding
Crew
Reviews
William Drew,Nov 2025
SJC - HNL
Overall
Comfort
Food
Entertainment
Boarding
Crew
Reviews
William Drew,Nov 2025
SJC - HNL
Overall
Comfort
Food
Entertainment
Boarding
Crew
Reviews
William Drew,Nov 2025
SJC - HNL
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$79 | Average$318 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$83 | Average$166 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$103 | Average$259 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$104 | Average$115 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$117 | Average$446 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$117 | Average$441 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$135 | Average$249 | FlexibilityNo cancel fee | On-time63% |