Use the FlyLogan App for real-time flight updates and pre-order food through BOS2GO to save time at the airport.
Most accurate provider | FlightHub 3 stars |
---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $121 (Kiwi.com) |
One-way from | $64 (United Airlines) |
Popular in | March |
Cheapest in | September |
Average price | $252 |
Good round-trip deal | $206 or less |
Good one-way deal | $128 or less |
Fly from
Fly to
Route
Depart
Return
Price
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Fri 10/31
2:05 pm-6:50 pm
1 stop5h 45m
Chicago Midway
Sat 11/1
5:35 pm-8:50 pm
Nonstop2h 15m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sat 11/1
11:45 am-1:40 pm
Nonstop2h 55m
Chicago O'Hare Intl
Sat 11/8
10:25 am-1:55 pm
Nonstop2h 30m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Tue 11/4
7:30 pm-9:19 pm
Nonstop2h 49m
Chicago O'Hare Intl
Sat 11/8
10:25 am-1:55 pm
Nonstop2h 30m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 11/5
7:20 am-9:22 am
Nonstop3h 02m
Chicago O'Hare Intl
Sat 11/8
10:25 am-1:55 pm
Nonstop2h 30m
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Wed 10/29
11:55 am-7:10 pm
2 stops8h 15m
Chicago Midway
Thu 10/30
6:05 am-9:20 am
Nonstop2h 15m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Tue 10/21
9:53 am-11:43 am
Nonstop2h 50m
Chicago O'Hare Intl
Mon 10/27
9:25 pm-12:45 am
Nonstop2h 20m
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Wed 10/22
9:10 am-6:30 pm
1 stop10h 20m
Chicago Midway
Thu 10/23
6:05 am-9:20 am
Nonstop2h 15m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Mon 1/5
6:23 pm-8:25 pm
Nonstop3h 02m
Chicago O'Hare Intl
Wed 1/7
7:30 am-10:52 am
Nonstop2h 22m
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Wed 10/29
5:40 pm-10:05 pm
1 stop5h 25m
Chicago Midway
Fri 10/31
8:00 am-3:55 pm
1 stop6h 55m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 10/23
7:20 am-9:22 am
Nonstop3h 02m
Chicago O'Hare Intl
Sat 10/25
3:50 pm-7:23 pm
Nonstop2h 33m
Provider | Price Accuracy | Trust Score* |
---|---|---|
Price Accuracy2 stars | Trust Score*3 stars | |
Price Accuracy3 stars | Trust Score*3 stars | |
Price Accuracy3 stars | Trust Score*3 stars | |
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*3 stars | |
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, November is the cheapest month in which you can book a flight from Boston to Chicago (average of $86). Flying from Boston to Chicago in December is currently the most expensive (average of $125). 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 17% on flights from Boston to Chicago by exploring options for tickets in the morning.
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 (83 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (46 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
Crew
Entertainment
Comfort
Food
Overall
Reviews
Mike,Aug 2025
OKC - AUS
Boarding
Crew
Entertainment
Comfort
Food
Overall
Reviews
Mike,Aug 2025
OKC - AUS
Boarding
Crew
Entertainment
Comfort
Food
Overall
Reviews
Mike,Aug 2025
OKC - AUS
Boarding
Crew
Entertainment
Comfort
Food
Overall
Reviews
Mike,Aug 2025
OKC - AUS
Boarding
Crew
Entertainment
Comfort
Food
Overall
Reviews
Mike,Aug 2025
OKC - AUS
Boarding
Crew
Entertainment
Comfort
Food
Overall
Reviews
Mike,Aug 2025
OKC - AUS
Airline | Cheapest | Average | Flexibility | On-time |
---|---|---|---|---|
Cheapest$69 | Average$245 | FlexibilityNo cancel fee | On-time65% | |
Cheapest$85 | Average$197 | FlexibilityNo cancel fee | On-time62% | |
Cheapest$100 | Average$106 | FlexibilityNo cancel fee | On-time62% | |
Cheapest$112 | Average$304 | FlexibilityNo cancel fee | On-timeN/A | |
Cheapest$117 | Average$239 | FlexibilityNo cancel fee | On-time63% | |
Cheapest$135 | Average$279 | FlexibilityNo cancel fee | On-time69% | |
Cheapest$136 | Average$257 | FlexibilityNo cancel fee | On-time71% |