Starting at $53
Starting at $53
Starting at $74
Starting at $179
Starting at $211
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 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.
Starting at $53
Starting at $53
Starting at $74
Starting at $179
Starting at $211
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.
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
United Airlines
Th and Fr
Starting at $90
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.
Boston — Chicago
04/10/2025
Departure date
Direct flight
WN576
Starting at $93
Boston — Chicago
04/24/2025
Departure date
Direct flight
WN576
Starting at $63
Boston — Chicago
05/10/2025
Departure date
Direct flight
AA3010
Starting at $113
Boston — Chicago
05/18/2025
Departure date
Direct flight
WN576
Starting at $223
Boston — Chicago
06/08/2025
Departure date
Direct flight
UA1414
Starting at $82
Boston — Chicago
06/17/2025
Departure date
Direct flight
UA2229
Starting at $166
Boston — Chicago
09/02/2025
Departure date
Direct flight
AA3324
Starting at $53
Boston — Chicago
05/04/2025
Departure date
Direct flight
WN2190
Starting at $176
Boston — Chicago
05/06/2025
Departure date
Direct flight
AA1509
Starting at $83
Boston — Chicago
05/10/2025
Departure date
Direct flight
AA1509
Starting at $177
The cheapest flight ticket from Boston to Chicago according to data for the last 48 hours costs $50
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: March, September, April.
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: Southwest Airlines, American Airlines, United Airlines
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.
The cheapest one-way flight from Boston to Chicago departs on 06/17/2025, is operated by JetBlue Airways and costs $50
The cheapest roundtrip flight from Boston to Chicago departs on 04/10/2025, is operated by American Airlines and costs $97
Fastest flight from Boston to Chicago takes 2h 35m
There are direct flights on this route 6 days a week: Su, Mo, Tu, Th, Fr, and Sa
The distance between Boston and Chicago is 1365km (846 miles). There are 51 direct flights from Boston to Chicago. The time difference between Boston and Chicago is 1h . Flights from Boston begin at 5:50 AM. The latest flight from Boston departs at 7:47 PM.
We couldn't find any special offers for flights from Boston to Chicago
