Use the FlyLogan App for real-time flight updates and pre-order food through BOS2GO to save time at the airport.

Most accurate provider | Mytrip 3 stars |
|---|---|
Most trusted provider | Mytrip 3 stars |
Round-trip from | $117 (Southwest) |
One-way from | $59 (Southwest) |
Popular in | March |
Cheapest in | September |
Average price | $247 |
Good round-trip deal | $191 or less |
Good one-way deal | $123 or less |
Fly from
Fly to
Route
Depart
Return
Price
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 12/10
8:30 am-10:35 am
Nonstop3h 05m
Chicago O'Hare Intl
Tue 12/16
11:25 am-2:49 pm
Nonstop2h 24m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 12/11
4:05 pm-6:02 pm
Nonstop2h 57m
Chicago O'Hare Intl
Sun 12/14
7:10 am-10:36 am
Nonstop2h 26m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sun 12/14
12:50 pm-2:47 pm
Nonstop2h 57m
Chicago O'Hare Intl
Wed 12/17
10:35 am-1:59 pm
Nonstop2h 24m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 12/10
8:30 am-10:35 am
Nonstop3h 05m
Chicago O'Hare Intl
Mon 12/15
8:38 pm-12:06 am
Nonstop2h 28m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Tue 12/9
8:30 am-10:35 am
Nonstop3h 05m
Chicago O'Hare Intl
Wed 12/17
11:25 am-2:49 pm
Nonstop2h 24m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 12/11
9:40 am-11:40 am
Nonstop3h 00m
Chicago O'Hare Intl
Sun 12/14
9:19 am-12:43 pm
Nonstop2h 24m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sat 12/13
12:50 pm-2:47 pm
Nonstop2h 57m
Chicago O'Hare Intl
Thu 12/18
7:10 am-10:36 am
Nonstop2h 26m
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Fri 12/12
6:50 pm-11:30 pm
1 stop5h 40m
Chicago Midway
Mon 12/15
6:15 pm-9:35 pm
Nonstop2h 20m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Tue 12/9
8:30 am-10:35 am
Nonstop3h 05m
Chicago O'Hare Intl
Fri 12/19
7:41 pm-11:10 pm
Nonstop2h 29m
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Tue 12/2
12:20 pm-7:10 pm
2 stops7h 50m
Chicago Midway
Wed 12/3
6:15 pm-9:35 pm
Nonstop2h 20m
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*1 star | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*2 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star |
The best time to book flights from Boston to Chicago is 90 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, April is the cheapest month in which you can book a flight from Boston to Chicago (average of $89). Flying from Boston to Chicago in January is currently the most expensive (average of $123). 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 afternoon, when flights are generally more expensive, you can save up to 18% 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 mornings 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 Thursday (75 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (27 on average).
Tampa (TPA) – chosen by Cheapflights users on 67% of 1-stop itineraries from Boston to Chicago on Cheapflights.
Tampa (TPA) is the most affordable 1-stop option, with an average round-trip price of $126.
Flights via Fort Lauderdale (FLL) have the shortest average one-way travel time for 1-stop routes: 10h 26m.
Flights via Fort Lauderdale (FLL) offer the fastest connection on this route, with an average layover time of 6h 16m.
Boarding
Comfort
Food
Overall
Entertainment
Crew
Reviews
Mike,Aug 2025
OKC - AUS
Boarding
Comfort
Food
Overall
Entertainment
Crew
Reviews
Mike,Aug 2025
OKC - AUS
Boarding
Comfort
Food
Overall
Entertainment
Crew
Reviews
Mike,Aug 2025
OKC - AUS
Boarding
Comfort
Food
Overall
Entertainment
Crew
Reviews
Mike,Aug 2025
OKC - AUS
Boarding
Comfort
Food
Overall
Entertainment
Crew
Reviews
Mike,Aug 2025
OKC - AUS
Boarding
Comfort
Food
Overall
Entertainment
Crew
Reviews
Mike,Aug 2025
OKC - AUS
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$71 | Average$255 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$79 | Average$195 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$89 | Average$116 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$116 | Average$286 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$117 | Average$238 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$126 | Average$276 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$135 | Average$256 | FlexibilityNo cancel fee | On-time71% |