Cheap Flights from Boston, MA to Chicago, IL from $59

Return flight: Chicago – Boston

On you will find 2 direct flights from Boston to Chicago. You can compare airfare deals from 1 airlines and multiple travel sites from $113, book and save on cheap plane tickets and last minute offers. Also check out BOS-CHI flight schedule to find best flight time, convenient departure and arrival airports.

Find One-Way and Round-Trip Boston to Chicago Flight Deals

To find the cheapest one way airline ticket select the date with the lowest price on the calendar below and click «Find Flights». To search for round-trip flight deals click on the link «Check prices for return flights» and select the date of the return flight. Cheapest flights in November: $59 (one-way), $101 (round-trip).
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Full flight schedule will help you in detecting at what time planes fly from Boston to Chicago. You can also specify the concrete flights and airlines on the route and how long the flight actually is. Use the calendar for today, tomorrow or other specific date as some flights are available only on certain days of the week.
Departure Arrival Flight Details Flight Duration Price
09:00 — 10:58
09:00 — 10:58 B64105 JetBlue
Boston — Chicago
2h 58m
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17:00 — 18:53
17:00 — 18:53 B64523 JetBlue
Boston — Chicago
2h 53m
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*Departure and arrival times - local. Updated on June 7, 2023

Flight Information

Below we will explain in detail what the flights cost on the destination from Boston to Chicago depends on and how to choose the most interesting flight option for you.

Distance between Boston and Chicago is 1370 miles. Time difference between the cities is 1h. Airplanes depart 09:00 to 17:00 from 4 Boston airports and arrive 09:00 to 17:00 to 7 Chicago airports. Average flight time is 2h 56m.

  • The fastest flight 2h 53m
  • Average flight time 2h 56m
  • The earliest flight 09:00
  • The latest flight 17:00
  • Distance 852 ml

The cheapest months to travel to Chicago are june (from 113 $), may (from 233 $).

What is the lowest airfare Boston to Chicago?

The cheapest plane ticket found by our users is $113. This airfare is for economy class on one-way B64105 flight by JetBlue for June 14, 2023 which leaves Logan in Boston at 09:00 am and arrives at Chicago O'Hare International at 10:58.

Economy class
Business class
First class

Popular Airlines on the Route

The flight Boston — Chicago is served by 1 regular airline and 1 low-cost airline. Most of the flights on this route are operated by JetBlue - 2 departures per week at the price of from $ 113 . And the most expensive tickets are offered by JetBlue airline - from $ 113.

Direct flights

There are 2 nonstop flights on the route. The fastest direct flight is B64523 by JetBlue takes 2h 53m and the cheapest is B64105 by JetBlue for $113.

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Connecting Flights

There’re no flights with layovers. Try direct flights or departure from nearby cities.


You can fly from Boston to Chicago from 4 airports (Boston City Heliport, Boston RT128 Rail, Boston South Rail, Logan).

Boston airports

  • Boston City Heliport-JBC
  • Boston RT128 Rail-ZRU
  • Boston South Rail-ZTO
  • Logan-BOS
    from $113

Chicago airports

  • O'Hare International-ORD
  • Midway-MDW
  • Dupage County-DPA
  • Chicago FSS-CHI
  • Merrill C Meigs (closed)-CGX
  • Pal-Waukee-PWK
  • Chicago NAS-NOH

How to book a plane ticket yourself?

How to book an air ticket yourself?
  • Fill in the search parameters — cities of departure and destination, departure and return dates and click «Find flights»
  • Select the best flight that you like. Please, check the airports of departure and arrival. Select the best fare, but pay attention to the following flight details - airports of departure and arrival, flight duration and layovers. Please use filters and sort to find the best flight.
  • Click «Buy» when you are ready — our system will redirect you to the site that sells the selected flight ticket.
  • Fill in all passenger and payment information — passport and contact information, please double check all passengers’ names and make a payment for your itinerary.
  • That's it — you will receive an email with your e-ticket usually within 10 minutes after your flight is confirmed. Please, print the e-ticket and have it with you at the airport. You would need to have only a passport and/or a required form of ID to travel. Please, check your Visa requirements if you travel outside of the United States or Canada.

    To find a plane ticket, please select dates.