
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $131 (Kiwi.com) |
One-way from | $66 (Kiwi.com) |
Popular in | April |
Cheapest in | January |
Average price | $207 |
Good round-trip deal | $165 or less |
Good one-way deal | $78 or less |
Fly from
Fly to
Route
Depart
Return
Price
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 4/29
9:41 am-1:09 pm
Nonstop2h 28m
Boston Logan Intl
Sat 5/2
7:35 pm-9:36 pm
Nonstop3h 01m
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 2/28
7:05 am-10:37 am
Nonstop2h 32m
Boston Logan Intl
Tue 3/3
3:50 pm-5:53 pm
Nonstop3h 03m
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 6/3
6:15 am-9:39 am
Nonstop2h 24m
Boston Logan Intl
Sat 6/6
6:00 am-7:58 am
Nonstop2h 58m
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 5/27
7:00 am-10:28 am
Nonstop2h 28m
Boston Logan Intl
Sat 5/30
7:00 am-8:58 am
Nonstop2h 58m
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Tue 4/21
9:41 am-1:09 pm
Nonstop2h 28m
Boston Logan Intl
Wed 5/13
6:52 am-8:51 am
Nonstop2h 59m
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Sat 2/28
11:45 am-7:15 pm
1 stop6h 30m
Boston Logan Intl
Sat 3/7
5:29 am-8:54 am
1 stop4h 25m
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 2/25
10:00 am-1:20 pm
Nonstop2h 20m
Boston Logan Intl
Wed 3/4
7:07 am-12:04 pm
1 stop5h 57m
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 4/22
8:31 am-2:16 pm
1 stop4h 45m
Boston Logan Intl
Tue 4/28
7:35 pm-9:36 pm
Nonstop3h 01m
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Wed 2/25
10:49 am-5:32 pm
1 stop5h 43m
Boston Logan Intl
Sat 2/28
5:29 am-8:54 am
1 stop4h 25m
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 2/28
1:02 pm-7:08 pm
1 stop5h 06m
Boston Logan Intl
Mon 3/2
6:28 pm-8:30 pm
Nonstop3h 02m
| 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 Accuracy2 stars | Trust Score*2 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
The price you pay for your flight from Chicago to Boston may vary depending on when you book. For the best chance of a lower fare, look to book 86 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
Currently, September is the cheapest month in which you can book a flight from Chicago to Boston (average of $91). Flying from Chicago to Boston in February is currently the most expensive (average of $117). 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.
It’s typically best to fly out from Chicago to Boston in the evening. Doing so could potentially save you 19% on the flight price compared to flying at noon, which is usually more expensive.
Travelers seeking maximum savings on their Chicago to Boston flight should consider departing on Saturday afternoons when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
The most flights from CHI to BOS are scheduled on a Thursday (56 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (19 on average).
About 23% of weekly flights between Chicago and Boston have experienced delays in the past year, with the average delay time being 149 minutes.
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the early afternoon 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, JetBlue have had the lowest number of delays on this route, with just 19% of flights being delayed.
Boarding
Comfort
Crew
Entertainment
Overall
Food
Reviews
Thomas,Dec 2025
SEA - DEN
Boarding
Comfort
Crew
Entertainment
Overall
Food
Reviews
Thomas,Dec 2025
SEA - DEN
Boarding
Comfort
Crew
Entertainment
Overall
Food
Reviews
Thomas,Dec 2025
SEA - DEN
Boarding
Comfort
Crew
Entertainment
Overall
Food
Reviews
Thomas,Dec 2025
SEA - DEN
Boarding
Comfort
Crew
Entertainment
Overall
Food
Reviews
Thomas,Dec 2025
SEA - DEN
Boarding
Comfort
Crew
Entertainment
Overall
Food
Reviews
Thomas,Dec 2025
SEA - DEN
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$61 | Average$157 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$79 | Average$158 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$94 | Average$217 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$117 | Average$232 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$117 | Average$254 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$136 | Average$245 | FlexibilityNo cancel fee | On-time63% |