American Airlines' Main Cabin Extra offers more legroom, enhancing comfort on short domestic flights.
American Airlines provides priority boarding with Main Cabin Extra, saving time for business travelers.
Most accurate provider | FlightHub 3 stars |
---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $113 (Kiwi.com) |
One-way from | $79 (JetBlue) |
Popular in | April |
Cheapest in | September |
Average price | $245 |
Fly from
Fly to
Route
Depart
Return
Price
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Mon 1/6
10:59 am-12:44 am
1 stop12h 45m
Boston Logan Intl
Wed 1/8
1:05 pm-7:51 pm
1 stop7h 46m
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Thu 1/9
5:02 pm-12:30 am
1 stop6h 28m
Boston Logan Intl
Mon 1/13
11:37 am-10:23 pm
1 stop11h 46m
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Tue 1/7
5:24 pm-12:30 am
1 stop6h 06m
Boston Logan Intl
Fri 1/10
6:00 am-11:51 am
1 stop6h 51m
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 2/1
10:29 am-9:44 pm
1 stop10h 15m
Boston Logan Intl
Wed 2/5
6:25 am-4:10 pm
1 stop10h 45m
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Thu 1/9
2:35 pm-6:10 pm
Nonstop2h 35m
Boston Logan Intl
Mon 1/13
7:15 am-9:25 am
Nonstop3h 10m
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Thu 1/9
10:05 am-1:20 pm
Nonstop2h 15m
Boston Logan Intl
Mon 1/13
8:10 am-10:05 am
Nonstop2h 55m
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Thu 1/16
7:00 am-10:15 am
Nonstop2h 15m
Boston Logan Intl
Sun 1/19
11:28 am-3:44 pm
1 stop5h 16m
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 2/15
12:20 pm-3:38 pm
Nonstop2h 18m
Boston Logan Intl
Wed 2/19
3:00 pm-5:04 pm
Nonstop3h 04m
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Thu 1/9
7:32 pm-8:26 am
1 stop11h 54m
Boston Logan Intl
Mon 1/13
3:50 pm-4:14 pm
1 stop25h 24m
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Fri 3/14
6:00 am-12:45 pm
1 stop5h 45m
Boston Logan Intl
Sun 3/16
6:00 am-8:04 am
Nonstop3h 04m
Provider | Price Accuracy | Trust Score* |
---|---|---|
Expedia | Price Accuracy1 star | Trust Score*3 stars |
FlightHub | Price Accuracy3 stars | Trust Score*3 stars |
eDreams | Price Accuracy3 stars | Trust Score*3 stars |
Priceline | Price Accuracy1 star | Trust Score*3 stars |
Cheapflightsfares | Price Accuracy3 stars | Trust Score*1 star |
CheapOair | Price Accuracy2 stars | Trust Score*2 stars |
Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
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 79 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
Currently, January is the cheapest month in which you can book a flight from Chicago to Boston (average of $218). Flying from Chicago to Boston in July is currently the most expensive (average of $311). 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 21% 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 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.
In terms of precipitation, rainfall in Boston ranges from 3.1 - 4.0 inches per month. March is typically the wettest month, when rainfall can reach 4.0 in. July is typically the driest time to visit Boston when rainfall is around 3.1 in.
If weather is an important factor for your trip to Boston, 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 30.2 F).
Crew
Overall
Comfort
Food
Boarding
Entertainment
Reviews
We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.
Crew
Overall
Comfort
Food
Boarding
Entertainment
Reviews
We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.
Crew
Overall
Comfort
Food
Boarding
Entertainment
Reviews
We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.
Crew
Overall
Comfort
Food
Boarding
Entertainment
Reviews
We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.
Crew
Overall
Comfort
Food
Boarding
Entertainment
Reviews
We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.
Crew
Overall
Comfort
Food
Boarding
Entertainment
Reviews
We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.
Airline | Cheapest | Average | Flexibility | On-time |
---|---|---|---|---|
Spirit Airlines | Cheapest$38 | Average$96 | FlexibilityNo cancel fee | On-time65% |
Delta | Cheapest$63 | Average$315 | FlexibilityNo cancel fee | On-timeN/A |
Frontier | Cheapest$69 | Average$116 | FlexibilityNo cancel fee | On-time62% |
JetBlue | Cheapest$84 | Average$241 | FlexibilityNo cancel fee | On-time62% |
American Airlines | Cheapest$138 | Average$258 | FlexibilityNo cancel fee | On-time71% |
United Airlines | Cheapest$149 | Average$295 | FlexibilityNo cancel fee | On-time69% |
Southwest | Cheapest$153 | Average$275 | FlexibilityNo cancel fee | On-time63% |