Cheapest flights from Chicago to Boston
Flaut.Travel was designed and developed by a team dedicated to making the process of searching, comparing and booking airline tickets as easy and convenient as possible. Our service helps travelers to find and buy the cheapest flights from Chicago to Boston. We have connected more than 40 airlines and airline ticketing agencies to help you find the most suitable and affordable flight option.
Cheapest one way flight
$66
Southwest Airlines
Direct flight
2h 15m
06/23/2025
The cheapest one-way flight from Chicago to Boston departs on 06/23/2025, is operated by Southwest Airlines and costs $66
Cheapest round trip flight
$131
JetBlue Airways
Direct flight
5h 24m
10/08/2025
The cheapest roundtrip flight from Chicago to Boston departs on 10/08/2025, is operated by JetBlue Airways and costs $131
The fastest flight
2h 10m
Fastest flight from Chicago to Boston takes 2h 10m
Direct flights
Several times a week
There are direct flights on this route 6 days a week: Su, Mo, Tu, We, Fr, and Sa
Earliest flight
5:30 AM
Latest flight
9:30 PM
Average flight duration
2h 28m
Direct flights count
83
Distance
1365km
Timezone difference
1h
The distance between Chicago and Boston is 1365km (846 miles). The average flight duration is 2h 28m. There are 83 direct flights from Chicago to Boston. The time difference between Chicago and Boston is 1h . Flights from Chicago begin at 5:30 AM. The latest flight from Chicago departs at 9:30 PM.
