
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $150 (Kiwi.com) |
One-way from | $76 (Frontier) |
Popular in | April |
Cheapest in | September |
Average price | $252 |
Good round-trip deal | $232 or less |
Good one-way deal | $126 or less |
Fly from
Fly to
Route
Depart
Return
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Sa 5/9
7:15 am-9:05 am
Nonstop2h 50m
Chicago Midway
Di 5/12
3:15 pm-6:35 pm
Nonstop2h 20m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Di 5/12
7:26 pm-11:37 pm
1 stop5h 11m
Chicago O'Hare Intl
Di 5/19
6:23 pm-9:59 pm
Nonstop2h 36m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Fr 5/8
7:30 am-9:30 am
Nonstop3h 00m
Chicago O'Hare Intl
Mo 5/11
8:00 pm-11:35 pm
Nonstop2h 35m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Di 6/2
7:27 pm-11:26 pm
1 stop4h 59m
Chicago O'Hare Intl
Do 6/4
6:15 am-9:39 am
Nonstop2h 24m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
So 8/23
6:00 am-7:58 am
Nonstop2h 58m
Chicago O'Hare Intl
Sa 8/29
7:46 pm-11:20 pm
Nonstop2h 34m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sa 5/9
12:00 pm-1:54 pm
Nonstop2h 54m
Chicago O'Hare Intl
So 5/10
7:00 am-10:35 am
Nonstop2h 35m
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Fr 6/5
6:45 pm-8:35 pm
Nonstop2h 50m
Chicago Midway
Di 6/9
6:05 pm-9:20 pm
Nonstop2h 15m
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Sa 5/9
9:25 am-11:05 am
Nonstop2h 40m
Chicago Midway
So 5/10
7:40 am-10:55 am
Nonstop2h 15m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sa 5/2
2:22 pm-6:33 pm
1 stop5h 11m
Chicago O'Hare Intl
Mi 5/6
12:45 pm-4:16 pm
Nonstop2h 31m
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Di 4/28
7:35 pm-9:39 pm
Nonstop3h 04m
Chicago O'Hare Intl
Fr 5/1
6:00 am-9:15 am
Nonstop2h 15m
| 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 Accuracy3 stars | 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 at noon, when flights are generally more expensive, you can save up to 25% 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 Thursday (66 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (31 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.
Crew
Overall
Food
Comfort
Boarding
Entertainment
Reviews
Dominic,Mar 2026
MCO - SMF
Crew
Overall
Food
Comfort
Boarding
Entertainment
Reviews
Dominic,Mar 2026
MCO - SMF
Crew
Overall
Food
Comfort
Boarding
Entertainment
Reviews
Dominic,Mar 2026
MCO - SMF
Crew
Overall
Food
Comfort
Boarding
Entertainment
Reviews
Dominic,Mar 2026
MCO - SMF
Crew
Overall
Food
Comfort
Boarding
Entertainment
Reviews
Dominic,Mar 2026
MCO - SMF
Crew
Overall
Food
Comfort
Boarding
Entertainment
Reviews
Dominic,Mar 2026
MCO - SMF
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$32 | Average$162 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$67 | Average$176 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$85 | Average$320 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$117 | Average$262 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$122 | Average$218 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$129 | Average$257 | FlexibilityNo cancel fee | On-time71% |