starting at $74
starting at $95
starting at $100
starting at $111
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.
A non-stop 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.
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Answers to questions about the route that travelers are most interested in.
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.
The route Boston — Chicago is served by many carriers — 4 in total, including JetBlue Airways, Southwest Airlines, United Airlines, and American Airlines. This gives passengers wide opportunities: from finding the lowest fare (from $74) to selecting flights by schedule or service class. Our service aggregates data from multiple booking systems so you can compare offers in one place. This saves time and money: no need to check dozens of sites — just pick the right option and book online.
starting at $74
starting at $95
starting at $100
starting at $111
Boston — Chicago
08/24/2026
Departure
Direct flight
B6311
starting at $74
Boston — Chicago
08/25/2026
Departure
Direct flight
B6311
starting at $79
Boston — Chicago
06/10/2026
Departure
Direct flight
B6311
starting at $95
Boston — Chicago
06/30/2026
Departure
Direct flight
WN745
starting at $95
Boston — Chicago
07/30/2026
Departure
Direct flight
UA1414
starting at $100
Boston — Chicago
11/10/2026
Departure
Direct flight
UA503
starting at $100
Boston — Chicago
09/27/2026
Departure
Direct flight
UA2229
starting at $100
Boston — Chicago
06/18/2026
Departure
Direct flight
UA1414
starting at $101
Boston — Chicago
06/29/2026
Departure
Direct flight
UA503
starting at $101
Boston — Chicago
04/23/2027
Departure
Direct flight
AA1509
starting at $111
There are most likely no direct flights on the Boston — Chicago route
We couldn't find any special offers for flights from Boston to Chicago
The cheapest one-way flight from Boston to Chicago departs on 08/24/2026, is operated by JetBlue Airways and costs $74
The cheapest roundtrip flight from Boston to Chicago departs on 09/10/2026, is operated by JetBlue Airways and costs $161
Fastest flight from Boston to Chicago takes 2h 35m
There are direct flights on this route 6 days a week: Su, Mo, Tu, We, Th, and Fr
The distance between Boston and Chicago is 1365km (846 miles). There are 134 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 10:05 PM
The cheapest flight ticket from Boston to Chicago according to data for the last 48 hours costs $74
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: August, June, July.
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, United Airlines
In different months, ticket prices from Boston to Chicago vary: minimum — $74 (August 2026), maximum — $111 (December 2026). Typically, the flight costs $99–$201.
Prices on the Boston — Chicago route are consistently going up. From June 2026 to April 2027, tickets went from $95 to $111 — a 17% increase. This trend is worth considering when planning your trip.
The most significant price increase was from August 2026 to April 2027 — up 50%. The best time to fly is July 2026–August 2026, when the average price is $87. In December 2026–April 2027, tickets cost around $111.
Given the rising prices, it's best not to delay your purchase. Flying in July 2026–August 2026 can save you up to 22% compared to the most expensive months.
Price variation across months on this route is 11.8%. Your choice of departure month significantly affects the total flight cost.