Flights

Flights from Chicago to Boston

Fares we've seen from Chicago (ORD) to Boston (BOS) start from US$106 on 3 Nov 2026 with JetBlue. Prices come from partner searches in the last 48 hours and change quickly, so look before you book.

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Compare Chicago to Boston on your dates and see current fares from our sources, listed by price.

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Fares by month

Month	Seen from	Date	Airline
October 2026	US$146	16 Oct 2026	Frontier · 1 stop	Check now
November 2026	US$106	3 Nov 2026	JetBlue · direct	Check now

One-way fares in US dollars, last seen on Aviasales. They can change at any time and may not be available on every day of the month. Partner links: we may earn a commission if you book, at no extra cost to you.

Airlines on this route

Airlines we've seen with fares on this route, listed by price:

JetBlue: from US$106 (direct)
Frontier: from US$146 (with a stop)
American Airlines: from US$147 (direct)

Plan the rest of your trip to Boston

Compare on Kiwi.comAnother source for the same trip, including mixed-airline itineraries Activities & Stays in BostonExperiences, day tours and hotel deals Things to do in BostonTours, tickets and experiences Attraction tickets in BostonMuseums, landmarks and shows Car rental in BostonCompare rental cars Car rental in BostonWorldwide car hire with free cancellation Local car hire in BostonCar rentals from verified local suppliers Airport transfer in BostonPre-booked door-to-door airport taxi Airport pickup in BostonTrained English-speaking drivers meeting you on arrival Airport transfer in Boston (Promo)Save on private transfers and shuttles with promo code Transfers in BostonBook transfers and rides with local drivers Travel eSIMMobile data abroad without roaming fees Yesim eSIM dataGlobal eSIM with unlimited data options Saily global eSIMTravel data eSIM powered by NordVPN Luggage storage in BostonSecure baggage storage near transit hubs Flight delayed or cancelled?Check if you're owed compensation Flight delay compensationUp to €600 compensation for flight delays or cancellations

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Questions about Chicago to Boston flights

How much do flights from Chicago to Boston cost? Fares we've seen start from US$106 on 3 Nov 2026 with JetBlue. Fares change quickly, so look before you book.

When can I save on flights from Chicago to Boston? Among the next six months we checked, November 2026 had fares from US$106 in our data, while October 2026 reached US$146. Prices vary by date, so compare several days and save.

Which airlines fly from Chicago to Boston? We've seen fares from JetBlue, Frontier, American Airlines. This reflects recent searches, not a complete timetable.

Are there direct flights from Chicago to Boston? Yes, we've seen direct fares (6 of 10 recent fares were direct). Availability depends on the date.

Is FindMyFlight free to use? Yes. We never add anything to the fare. If you book through a partner link we may earn a commission from the partner, at no extra cost to you.