Starting at $65
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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 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.
Starting at $65
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Starting at $132
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Starting at $228
United Airlines
Every day
Starting at $98
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
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.
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.
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.
The cheapest one-way flight from Chicago to Boston departs on 05/12/2025, is operated by Spirit Airlines and costs $52
The cheapest roundtrip flight from Chicago to Boston departs on 05/01/2025, is operated by JetBlue Airways and costs $141
Fastest flight from Chicago to Boston takes 2h 24m
There are direct flights on this route 2 days a week: Su and Fr
The distance between Chicago and Boston is 1365km (846 miles). The average flight duration is 2h 17m. There are 128 direct flights from Chicago to Boston. The time difference between Chicago and Boston is 1h . Flights from Chicago begin at 6:00 AM. The latest flight from Chicago departs at 8:20 PM.
Chicago — Boston
03/16/2025
Departure date
Direct flight
UA450
Starting at $312
Chicago — Boston
03/23/2025
Departure date
Direct flight
AA3703
Starting at $832
Chicago — Boston
05/10/2025
Departure date
Direct flight
WN1132
Starting at $110
Chicago — Boston
05/11/2025
Departure date
Direct flight
B6312
Starting at $170
Chicago — Boston
05/16/2025
Departure date
Direct flight
WN1132
Starting at $269
Chicago — Boston
05/17/2025
Departure date
Direct flight
YX4394
Starting at $155
Chicago — Boston
05/18/2025
Departure date
Direct flight
UA399
Starting at $401
Chicago — Boston
03/23/2025
Departure date
Direct flight
AA4462
Starting at $294
Chicago — Boston
05/12/2025
Departure date
Direct flight
WN404
Starting at $116
Chicago — Boston
07/05/2025
Departure date
Direct flight
UA1779
Starting at $247
The cheapest flight ticket from Chicago to Boston according to data for the last 48 hours costs $52
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: May, March, June.
The fastest flights from Chicago to Boston start from 2 hours 24 minutes in the air.
The following airlines operate direct flights on the route Chicago — Boston: United Airlines, American Airlines, Southwest Airlines
We couldn't find any special offers for flights from Chicago to Boston
