starting at $45
starting at $66
starting at $68
starting at $97
starting at $108
starting at $108
Compare airlines, prices, and flight durations for your trip
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.
A non-stop 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.
A direct flight is the easiest way to get to your destination. The following airlines operate non-stop flights from Chicago to Boston:
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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 Chicago — Boston route is served by a wide range of airlines: 6 in total, including JetBlue Airways, American Airlines, Southwest Airlines, United Airlines, Frontier Airlines, and Spirit Airlines. Competition among carriers gives passengers the opportunity to find tickets at attractive fares — with prices starting from $45. Our service helps compare all available offers within seconds and choose the most convenient option. You can filter flights by price, departure time, or baggage rules to make your trip as comfortable as possible. With so many airlines, there’s always a chance to catch special promotions and save.
starting at $45
starting at $66
starting at $68
starting at $97
starting at $108
starting at $108
Chicago — Boston
02/09/2026
Departure
Direct flight
B6312
starting at $45
Chicago — Boston
02/01/2026
Departure
Direct flight
AA3710
starting at $66
Chicago — Boston
04/28/2026
Departure
Direct flight
B6312
starting at $66
Chicago — Boston
02/02/2026
Departure
Direct flight
B6312
starting at $68
Chicago — Boston
02/07/2026
Departure
Direct flight
WN987
starting at $68
Chicago — Boston
01/31/2026
Departure
Direct flight
B6312
starting at $72
Chicago — Boston
02/08/2026
Departure
Direct flight
B6312
starting at $72
Chicago — Boston
02/07/2026
Departure
Direct flight
WN4806
starting at $73
Chicago — Boston
02/27/2026
Departure
Direct flight
WN987
starting at $79
Chicago — Boston
02/13/2026
Departure
Direct flight
WN987
starting at $81
American Airlines
Every day
starting at $190
United Airlines
Every day
starting at $224
We couldn't find any special offers for flights from Chicago to Boston
The cheapest one-way flight from Chicago to Boston departs on 02/09/2026, is operated by JetBlue Airways and costs $45
The cheapest roundtrip flight from Chicago to Boston departs on 02/18/2026, is operated by Southwest Airlines and costs $32
Fastest flight from Chicago to Boston takes 2h 15m
There are direct flights on this route 5 days a week: Su, Mo, Tu, Fr, and Sa
The distance between Chicago and Boston is 1365km (846 miles). The average flight duration is 2h 36m. There are 156 direct flights from Chicago to Boston. The time difference between Chicago and Boston is 1h. Flights from Chicago begin at 6:10 AM. The latest flight from Chicago departs at 8:40 PM
The cheapest flight ticket from Chicago to Boston according to data for the last 48 hours costs $45
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: February, April, January.
The fastest flights from Chicago to Boston start from 2 hours 15 minutes in the air.
The following airlines operate direct flights on the route Chicago — Boston: JetBlue Airways, American Airlines, Southwest Airlines
The minimum one-way ticket price from Chicago to Boston is $45 (February 2026), while the maximum is $97 (March 2026). On average, a ticket costs $70–$72.