United's Economy Plus offers extra legroom, perfect for comfort on short flights.
United's MileagePlus program allows pooling miles, useful for frequent flyers.
Round-trip from | $137 (Southwest) |
---|---|
One-way from | $69 (Southwest) |
Popular in | March |
Cheapest in | September |
Average price | $223 |
Good round-trip deal | $137 or less |
Good one-way deal | $123 or less |
Fly from
Fly to
Route
Depart
Return
Price
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Tue 7/15
7:20 am-9:00 am
Nonstop2h 40m
Chicago Midway
Thu 7/17
8:05 am-11:20 am
Nonstop2h 15m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Fri 8/22
7:55 pm-9:54 pm
Nonstop2h 59m
Chicago O'Hare Intl
Tue 8/26
7:00 am-10:29 am
Nonstop2h 29m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 7/30
8:39 pm-8:55 am
1 stop13h 16m
Chicago O'Hare Intl
Wed 8/6
5:05 am-7:34 pm
1 stop13h 29m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Tue 7/15
2:55 pm-5:02 pm
Nonstop3h 07m
Chicago O'Hare Intl
Thu 7/17
8:30 pm-12:14 am
Nonstop2h 44m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 8/21
8:47 am-4:57 pm
1 stop9h 10m
Chicago O'Hare Intl
Sat 8/23
7:46 pm-8:35 am
1 stop11h 49m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Tue 7/15
7:04 pm-11:41 pm
1 stop5h 37m
Chicago O'Hare Intl
Tue 7/22
3:48 pm-7:18 pm
Nonstop2h 30m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 7/24
8:47 am-4:40 pm
1 stop8h 53m
Chicago O'Hare Intl
Tue 7/29
10:00 am-7:30 pm
1 stop8h 30m
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Sat 8/16
9:40 am-8:22 pm
1 stop11h 42m
Chicago Midway
Sun 8/17
3:58 pm-12:38 am
1 stop7h 40m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Tue 7/15
5:45 am-11:50 am
1 stop7h 05m
Chicago O'Hare Intl
Sat 7/19
1:30 pm-9:05 pm
1 stop6h 35m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sat 7/26
7:00 am-8:55 am
Nonstop2h 55m
Chicago O'Hare Intl
Tue 7/29
8:40 am-12:04 pm
Nonstop2h 24m
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, August is the cheapest month in which you can book a flight from Boston to Chicago (average of $245). Flying from Boston to Chicago in March is currently the most expensive (average of $321). 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 26% 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 Wednesday 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 Thursday (80 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (5 on average).
Overall
Food
Boarding
Crew
Comfort
Entertainment
Reviews
John,May 2025
PVD - BNA
Overall
Food
Boarding
Crew
Comfort
Entertainment
Reviews
John,May 2025
PVD - BNA
Overall
Food
Boarding
Crew
Comfort
Entertainment
Reviews
John,May 2025
PVD - BNA
Overall
Food
Boarding
Crew
Comfort
Entertainment
Reviews
John,May 2025
PVD - BNA
Overall
Food
Boarding
Crew
Comfort
Entertainment
Reviews
John,May 2025
PVD - BNA
Overall
Food
Boarding
Crew
Comfort
Entertainment
Reviews
John,May 2025
PVD - BNA
Airline | Cheapest | Average | Flexibility | On-time |
---|---|---|---|---|
Cheapest$41 | Average$111 | FlexibilityNo cancel fee | On-time65% | |
Cheapest$78 | Average$203 | FlexibilityNo cancel fee | On-time62% | |
Cheapest$94 | Average$312 | FlexibilityNo cancel fee | On-timeN/A | |
Cheapest$97 | Average$233 | FlexibilityNo cancel fee | On-time69% | |
Cheapest$100 | Average$117 | FlexibilityNo cancel fee | On-time62% | |
Cheapest$124 | Average$303 | FlexibilityNo cancel fee | On-time63% | |
Cheapest$136 | Average$254 | FlexibilityNo cancel fee | On-time71% |