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 | $123 (Southwest) |
---|---|
One-way from | $63 (Southwest) |
Popular in | March |
Cheapest in | September |
Average price | $222 |
Good round-trip deal | $146 or less |
Good one-way deal | $111 or less |
Fly from
Fly to
Route
Depart
Return
Price
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
mar. 7/1
6:50 pm-8:35 pm
Nonstop2h 45m
Chicago Midway
sáb. 7/12
7:00 pm-10:15 pm
Nonstop2h 15m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
lun. 6/30
6:15 am-6:44 pm
1 stop13h 29m
Chicago O'Hare Intl
mié. 7/9
10:00 am-7:30 pm
1 stop8h 30m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
vie. 9/5
7:00 am-8:57 am
Nonstop2h 57m
Chicago O'Hare Intl
lun. 9/8
9:42 am-1:10 pm
Nonstop2h 28m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
mar. 7/1
5:45 am-11:00 am
1 stop6h 15m
Chicago O'Hare Intl
sáb. 7/12
4:45 pm-11:40 pm
1 stop5h 55m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
mar. 7/1
7:04 pm-11:37 pm
1 stop5h 33m
Chicago O'Hare Intl
vie. 7/4
3:48 pm-7:18 pm
Nonstop2h 30m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
lun. 6/30
7:20 am-9:18 am
Nonstop2h 58m
Chicago O'Hare Intl
vie. 7/4
2:15 pm-5:54 pm
Nonstop2h 39m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
vie. 8/15
5:29 am-7:25 am
Nonstop2h 56m
Chicago O'Hare Intl
dom. 8/24
7:00 am-10:24 am
Nonstop2h 24m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
sáb. 7/5
6:00 am-7:20 pm
1 stop14h 20m
Chicago O'Hare Intl
mié. 7/9
10:00 am-11:03 pm
1 stop12h 03m
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
lun. 6/30
9:40 am-8:17 pm
1 stop11h 37m
Chicago Midway
jue. 7/10
3:58 pm-12:38 am
1 stop7h 40m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
sáb. 6/28
6:00 am-7:03 pm
1 stop14h 03m
Chicago O'Hare Intl
lun. 7/14
8:27 pm-7:59 am
1 stop10h 32m
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 Monday (85 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (64 on average).
In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.
If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).
Crew
Entertainment
Overall
Boarding
Food
Comfort
Reviews
James,Apr 2025
LAX - SFO
Crew
Entertainment
Overall
Boarding
Food
Comfort
Reviews
James,Apr 2025
LAX - SFO
Crew
Entertainment
Overall
Boarding
Food
Comfort
Reviews
James,Apr 2025
LAX - SFO
Crew
Entertainment
Overall
Boarding
Food
Comfort
Reviews
James,Apr 2025
LAX - SFO
Crew
Entertainment
Overall
Boarding
Food
Comfort
Reviews
James,Apr 2025
LAX - SFO
Crew
Entertainment
Overall
Boarding
Food
Comfort
Reviews
James,Apr 2025
LAX - SFO
Airline | Cheapest | Average | Flexibility | On-time |
---|---|---|---|---|
Cheapest$39 | Average$107 | FlexibilityNo cancel fee | On-time65% | |
Cheapest$79 | Average$202 | FlexibilityNo cancel fee | On-time62% | |
Cheapest$93 | Average$310 | FlexibilityNo cancel fee | On-timeN/A | |
Cheapest$97 | Average$234 | FlexibilityNo cancel fee | On-time69% | |
Cheapest$100 | Average$120 | FlexibilityNo cancel fee | On-time62% | |
Cheapest$126 | Average$304 | FlexibilityNo cancel fee | On-time63% | |
Cheapest$137 | Average$255 | FlexibilityNo cancel fee | On-time71% |