Starting at $44
Starting at $47
Starting at $48
Starting at $67
Starting at $133
Helping travelers to find the best flight offers
A direct flight is the easiest way to get to your destination. The following airlines operate non-stop flights from Chicago to Boston:
We keep tight track on airlines' pre-holidays sales and other special offers occurences all the time to let you save maximum amount of funds while traveling to your family or just going out on vacation.
Starting at $44
Starting at $47
Starting at $48
Starting at $67
Starting at $133
American Airlines
Mo, We, and Th
Starting at $150
United Airlines
Mo, We, and Th
Starting at $171
JetBlue Airways
Mo, We, and Th
Starting at $94
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.
Below you will find a list of airlines operating flights on the Chicago — Boston route and the starting prices for flights of each specific airline on it.
We carefully collect statistics on the search and pricing of airlines and, based on these data, we make an assumption about future prices. Thus, you can better understand which season is the cheapest to fly from Chicago to Boston
A direct flight is the most convenient and comfortable way to fly from Chicago to Boston, despite the fact that sometimes flights with transfers can cost significantly less.
The cheapest one-way flight from Chicago to Boston departs on 06/25/2025, is operated by JetBlue Airways and costs $59
The cheapest roundtrip flight from Chicago to Boston departs on 05/29/2025, is operated by JetBlue Airways and costs $119
Fastest flight from Chicago to Boston takes 2h 28m
There are direct flights on this route 6 days a week: Su, Tu, We, Th, Fr, and Sa
The distance between Chicago and Boston is 1365km (846 miles). The average flight duration is 2h 17m. There are 128 direct flights from Chicago to Boston. The time difference between Chicago and Boston is 1h . Flights from Chicago begin at 6:00 AM. The latest flight from Chicago departs at 8:20 PM.
Chicago — Boston
04/12/2025
Departure date
Direct flight
AA4404
Starting at $185
Chicago — Boston
04/19/2025
Departure date
Direct flight
WN1132
Starting at $221
Chicago — Boston
04/26/2025
Departure date
Direct flight
UA580
Starting at $1,125
Chicago — Boston
04/30/2025
Departure date
Direct flight
AA3107
Starting at $311
Chicago — Boston
05/03/2025
Departure date
Direct flight
AA3325
Starting at $64
Chicago — Boston
05/06/2025
Departure date
Direct flight
WN1915
Starting at $124
Chicago — Boston
05/19/2025
Departure date
Direct flight
B6312
Starting at $161
Chicago — Boston
05/22/2025
Departure date
Direct flight
AA630
Starting at $217
Chicago — Boston
05/26/2025
Departure date
Direct flight
WN404
Starting at $181
Chicago — Boston
04/13/2025
Departure date
Direct flight
B6612
Starting at $255
The cheapest flight ticket from Chicago to Boston according to data for the last 48 hours costs $59
Often the best time to buy tickets from Chicago to Boston is 2 months before departure.
Based on statistics over the past years, the lowest prices for flights from Chicago to Boston can be found flying in these months: June, May, September.
The fastest flights from Chicago to Boston start from 2 hours 28 minutes in the air.
The following airlines operate direct flights on the route Chicago — Boston: American Airlines, Southwest Airlines, United Airlines
We couldn't find any special offers for flights from Chicago to Boston
