Flights

Flights from Boston to Chicago

Fares we've seen from Boston (BOS) to Chicago (ORD) start from US$95 on 27 Oct 2026 with Frontier. Prices come from partner searches in the last 48 hours and change quickly, so look before you book.

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

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Fares by month

MonthSeen fromDateAirline
October 2026US$9527 Oct 2026Frontier · 1 stopCheck now
November 2026US$1063 Nov 2026JetBlue · directCheck now
December 2026US$1058 Dec 2026JetBlue · directCheck 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:

  • Frontier: from US$95 (with a stop)
  • JetBlue: from US$105 (direct)
  • American Airlines: from US$156 (direct)
  • United: from US$191 (direct)

Plan the rest of your trip to Chicago

Compare on Kiwi.comAnother source for the same trip, including mixed-airline itinerariesActivities & Stays in ChicagoExperiences, day tours and hotel dealsThings to do in ChicagoTours, tickets and experiencesAttraction tickets in ChicagoMuseums, landmarks and showsCar rental in ChicagoCompare rental carsCar rental in ChicagoWorldwide car hire with free cancellationLocal car hire in ChicagoCar rentals from verified local suppliersAirport transfer in ChicagoPre-booked door-to-door airport taxiAirport pickup in ChicagoTrained English-speaking drivers meeting you on arrivalAirport transfer in Chicago (Promo)Save on private transfers and shuttles with promo codeTransfers in ChicagoBook transfers and rides with local driversTravel eSIMMobile data abroad without roaming feesYesim eSIM dataGlobal eSIM with unlimited data optionsSaily global eSIMTravel data eSIM powered by NordVPNLuggage storage in ChicagoSecure baggage storage near transit hubsFlight delayed or cancelled?Check if you're owed compensationFlight delay compensationUp to €600 compensation for flight delays or cancellations

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Questions about Boston to Chicago flights

How much do flights from Boston to Chicago cost? Fares we've seen start from US$95 on 27 Oct 2026 with Frontier. Fares change quickly, so look before you book.

When can I save on flights from Boston to Chicago? Among the next six months we checked, October 2026 had fares from US$95 in our data, while November 2026 reached US$106. Prices vary by date, so compare several days and save.

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

Are there direct flights from Boston to Chicago? Yes, we've seen direct fares (13 of 17 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.

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