Airlines operating on route
Starting at $56
Starting at $56
Starting at $57
Starting at $59
Starting at $61
Starting at $64
Starting at $126
Helping travelers to find the best flight offers
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.
Starting at $56
Starting at $56
Starting at $57
Starting at $59
Starting at $61
Starting at $64
Starting at $126
Chicago — Boston
05/10/2025
Departure date
Direct flight
UA1532
Starting at $159
Chicago — Boston
05/11/2025
Departure date
Direct flight
UA2067
Starting at $68
Chicago — Boston
05/18/2025
Departure date
Direct flight
WN1915
Starting at $187
Chicago — Boston
05/21/2025
Departure date
Direct flight
WN1240
Starting at $125
Chicago — Boston
05/23/2025
Departure date
Direct flight
AA3010
Starting at $273
Chicago — Boston
05/27/2025
Departure date
Direct flight
WN3273
Starting at $181
Chicago — Boston
06/13/2025
Departure date
Direct flight
AA2682
Starting at $101
Chicago — Boston
06/27/2025
Departure date
Direct flight
WN3786
Starting at $212
Chicago — Boston
07/25/2025
Departure date
Direct flight
AA547
Starting at $105
Chicago — Boston
09/24/2025
Departure date
Direct flight
B6312
Starting at $62
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.
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.
Southwest Airlines
Every day
Starting at $125
American Airlines
Su, Mo, Tu, and Sa
Starting at $67
United Airlines
Su, Mo, Tu, and Sa
Starting at $89
JetBlue Airways
Su, Mo, Tu, and Sa
Starting at $78
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.
The cheapest flight ticket from Chicago to Boston according to data for the last 48 hours costs $56
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: July, September, May.
The fastest flights from Chicago to Boston start from 2 hours 23 minutes in the air.
The following airlines operate direct flights on the route Chicago — Boston: United Airlines, Southwest Airlines, American Airlines
The cheapest one-way flight from Chicago to Boston departs on 07/26/2025, is operated by American Airlines and costs $56
The cheapest roundtrip flight from Chicago to Boston departs on 07/16/2025, is operated by JetBlue Airways and costs $113
Fastest flight from Chicago to Boston takes 2h 23m
There are direct flights on this route 5 days a week: Su, Tu, We, Th, and Sa
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.
травень 28
Southwest Airlines
