
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $150 (Delta) |
One-way from | $76 (Frontier) |
Popular in | April |
Cheapest in | September |
Average price | $259 |
Good round-trip deal | $234 or less |
Good one-way deal | $133 or less |
Fly from
Fly to
Route
Depart
Return
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
mar. 6/2
3:00 pm-8:26 pm
1 stop6h 26m
Chicago O'Hare Intl
sáb. 6/6
5:19 pm-11:29 pm
1 stop5h 10m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
jue. 5/28
5:51 am-11:47 am
1 stop6h 56m
Chicago O'Hare Intl
mar. 6/2
7:05 am-2:15 pm
1 stop6h 10m
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
mar. 8/18
7:15 pm-8:50 pm
Nonstop2h 35m
Chicago Midway
mar. 8/25
1:00 pm-10:10 pm
2 stops8h 10m
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
vie. 9/11
8:20 pm-10:00 pm
Nonstop2h 40m
Chicago Midway
lun. 9/14
5:45 am-9:00 am
Nonstop2h 15m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
lun. 5/25
6:00 am-7:58 am
Nonstop2h 58m
Chicago O'Hare Intl
jue. 5/28
7:33 am-11:05 am
Nonstop2h 32m
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
sáb. 5/2
3:30 pm-5:15 pm
Nonstop2h 45m
Chicago Midway
vie. 5/8
7:00 pm-10:20 pm
Nonstop2h 20m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
mar. 6/9
5:45 am-9:36 am
1 stop4h 51m
Chicago O'Hare Intl
jue. 6/11
9:26 pm-12:59 am
Nonstop2h 33m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
dom. 5/24
5:45 am-9:36 am
1 stop4h 51m
Chicago O'Hare Intl
lun. 5/25
6:15 am-9:39 am
Nonstop2h 24m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
sáb. 5/30
9:00 am-1:21 pm
1 stop5h 21m
Chicago O'Hare Intl
lun. 6/1
7:00 am-10:35 am
Nonstop2h 35m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
jue. 5/7
9:20 am-11:20 am
Nonstop3h 00m
Chicago O'Hare Intl
lun. 5/11
8:00 pm-11:35 pm
Nonstop2h 35m
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
The best time to book flights from Boston to Chicago is 78 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.
Currently, September is the cheapest month in which you can book a flight from Boston to Chicago (average of $166). Flying from Boston to Chicago in April is currently the most expensive (average of $296). 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 24% on flights from Boston to Chicago by exploring options for tickets in the evening.
Travelers seeking maximum savings on their Boston to Chicago flight should consider departing on Thursday evenings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
The most flights from BOS to CHI are scheduled on a Monday (65 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (33 on average).
About 15% of weekly flights between Boston and Chicago have experienced delays in the past year, with the average delay time being 172 minutes.
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.
Saturday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.
Over the last year, United Airlines have had the lowest number of delays on this route, with just 10% of flights being delayed.
Boarding
Comfort
Crew
Entertainment
Food
Overall
Reviews
Dominic,Mar 2026
MCO - SMF
Boarding
Comfort
Crew
Entertainment
Food
Overall
Reviews
Dominic,Mar 2026
MCO - SMF
Boarding
Comfort
Crew
Entertainment
Food
Overall
Reviews
Dominic,Mar 2026
MCO - SMF
Boarding
Comfort
Crew
Entertainment
Food
Overall
Reviews
Dominic,Mar 2026
MCO - SMF
Boarding
Comfort
Crew
Entertainment
Food
Overall
Reviews
Dominic,Mar 2026
MCO - SMF
Boarding
Comfort
Crew
Entertainment
Food
Overall
Reviews
Dominic,Mar 2026
MCO - SMF
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$32 | Average$187 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$67 | Average$176 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$87 | Average$321 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$118 | Average$263 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$125 | Average$217 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$130 | Average$258 | FlexibilityNo cancel fee | On-time71% |