Airlines operating on route
Starting at $67
Starting at $68
Starting at $71
Starting at $1,732
Helping travelers to find the best flight offers
Starting at $67
Starting at $68
Starting at $71
Starting at $1,732
Boston — Chicago
09/04/2025
Departure date
Direct flight
B6811
Starting at $67
Boston — Chicago
07/24/2025
Departure date
Direct flight
WN1433
Starting at $68
Boston — Chicago
07/15/2025
Departure date
Direct flight
WN1375
Starting at $70
Boston — Chicago
08/15/2025
Departure date
Direct flight
AA3324
Starting at $71
Boston — Chicago
09/02/2025
Departure date
Direct flight
AA547
Starting at $71
Boston — Chicago
08/19/2025
Departure date
Direct flight
B6311
Starting at $72
Boston — Chicago
10/04/2025
Departure date
Direct flight
WN1482
Starting at $72
Boston — Chicago
11/06/2025
Departure date
Direct flight
B6311
Starting at $72
Boston — Chicago
07/12/2025
Departure date
Direct flight
B6311
Starting at $74
Boston — Chicago
10/28/2025
Departure date
Direct flight
B6811
Starting at $75
A direct flight is the easiest way to get to your destination. The following airlines operate non-stop flights from Boston to Chicago:
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.
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 Boston to Chicago. We have connected more than 40 airlines and airline ticketing agencies to help you find the most suitable and affordable flight option.
Southwest Airlines
We and Sa
Starting at $124
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 Boston to Chicago
Below you will find a list of airlines operating flights on the Boston — Chicago route and the starting prices for flights of each specific airline on it.
A direct flight is the most convenient and comfortable way to fly from Boston to Chicago, despite the fact that sometimes flights with transfers can cost significantly less.
We couldn't find any special offers for flights from Boston to Chicago
The cheapest flight ticket from Boston to Chicago according to data for the last 48 hours costs $67
Often the best time to buy tickets from Boston to Chicago is 2 months before departure.
Based on statistics over the past years, the lowest prices for flights from Boston to Chicago can be found flying in these months: July, August, November.
The fastest flights from Boston to Chicago start from 2 hours 35 minutes in the air.
The following airlines operate direct flights on the route Boston — Chicago: JetBlue Airways, Southwest Airlines, American Airlines
The cheapest one-way flight from Boston to Chicago departs on 09/04/2025, is operated by JetBlue Airways and costs $67
The cheapest roundtrip flight from Boston to Chicago departs on 09/10/2025, is operated by JetBlue Airways and costs $84
Fastest flight from Boston to Chicago takes 2h 35m
There are direct flights on this route 5 days a week: Su, Tu, Th, Fr, and Sa
The distance between Boston and Chicago is 1365km (846 miles). There are 161 direct flights from Boston to Chicago. The time difference between Boston and Chicago is 1h . Flights from Boston begin at 5:00 AM. The latest flight from Boston departs at 8:25 PM.
