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.
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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 Allegiant Air. Competition among carriers gives passengers the opportunity to find tickets at attractive fares — with prices starting from $105. 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 $105
starting at $141
starting at $158
starting at $185
starting at $108
starting at $149
Chicago — Boston
11/09/2026
Departure
Direct flight
B61012
starting at $105
Chicago — Boston
11/15/2026
Departure
Direct flight
AA3067
starting at $141
Chicago — Boston
11/12/2026
Departure
Direct flight
AA469
starting at $158
Chicago — Boston
11/08/2026
Departure
Direct flight
WN4113
starting at $158
Chicago — Boston
11/10/2026
Departure
Direct flight
AA482
starting at $159
Chicago — Boston
03/24/2027
Departure
Direct flight
B6312
starting at $175
Chicago — Boston
11/14/2026
Departure
Direct flight
B6112
starting at $177
Chicago — Boston
11/30/2026
Departure
Direct flight
UA2296
starting at $185
Chicago — Boston
11/28/2026
Departure
Direct flight
UA2213
starting at $253
Chicago — Boston
11/29/2026
Departure
Direct flight
WN3014
starting at $371
All airports
Ticket prices for Chicago — Boston follow a predictable curve: rise, peak, and decline. This typical seasonal pattern lets you plan your purchase to avoid overpaying.
Prices rise from November 2026 to March 2027 (+73%), then decline from March 2027 to July 2027 (5%). The cheapest tickets are in November 2026–December 2026 (averaging $108), while the priciest are in March 2027–July 2027 ($182).
For savings, plan your flight for November 2026–December 2026 — you could save up to 41%. Try to avoid March 2027–July 2027 when possible: prices are at their highest then.
Price spread on this route is 25.5%. Costs depend heavily on the season, so flexibility in choosing your departure month is especially valuable here.
The minimum one-way ticket price from Chicago to Boston is $108 (November 2026), while the maximum is $187 (March 2027). On average, a ticket costs $145–$177.
The cheapest flight ticket from Chicago to Boston according to data for the last 48 hours costs $105
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: November, December, July.
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
American Airlines
Su, Mo, Tu, We, Th, and Fr
starting at $104
United Airlines
Su, Mo, Tu, We, Th, and Fr
starting at $97
The airlines on the Chicago — Boston route each fly on specific days: American Airlines and United Airlines fly every day except Saturday.
The cheapest one-way flight from Chicago to Boston departs on 11/09/2026, is operated by JetBlue Airways and costs $105
The cheapest roundtrip flight from Chicago to Boston departs on 11/21/2026, is operated by JetBlue Airways and costs $244
Fastest flight from Chicago to Boston takes 2h 15m
There are direct flights on this route 6 days a week: Su, Mo, Tu, We, Th, and Sa
The distance between Chicago and Boston is 1365km (846 miles). The average flight duration is 2h 20m. There are 126 direct flights from Chicago to Boston. The time difference between Chicago and Boston is 1h. Flights from Chicago begin at 5:30 AM. The latest flight from Chicago departs at 9:20 PM
We couldn't find any special offers for flights from Chicago to Boston