Cheap Flights from Chicago, IL to Boston, MA from $61

Return flight: Boston – Chicago

On Cheapflightsplus.com you will find 3 direct and 3 connecting flights from Chicago to Boston. You can compare airfare deals from 2 airlines and multiple travel sites from $214, book and save on cheap plane tickets and last minute offers. Also check out CHI-BOS flight schedule to find best flight time, convenient departure and arrival airports.

Find One-Way and Round-Trip Chicago to Boston 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: $61 (one-way), $105 (round-trip).
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Full flight schedule will help you in detecting at what time planes fly from Chicago to Boston. 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
10:40 — 13:56
10:40 — 13:56 AA2264 American Airlines
Chicago — Boston
2h 16m
Find flight
from$214
17:24 — 20:38
17:24 — 20:38 B64312 JetBlue
Chicago — Boston
2h 14m
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from$304
05:25 — 11:43
05:25 — 08:20 AA1784 American Airlines
Chicago — Charlotte
1h 8m stop
09:28 — 11:43 AA1180 American Airlines
Charlotte — Boston
5h 18m
including layover
Find flight
from$265
12:30 — 19:32
12:30 — 15:22 AA2795 American Airlines
Chicago — Charlotte
2h 1m stop
17:23 — 19:32 AA2252 American Airlines
Charlotte — Boston
6h 2m
including layover
Find flight
from$377
16:40 — 22:58
16:40 — 19:31 AA815 American Airlines
Chicago — Charlotte
1h 15m stop
20:46 — 22:58 AA1843 American Airlines
Charlotte — Boston
5h 18m
including layover
Find flight
from$265
*Departure and arrival times - local. Updated on November 29, 2022

Flight Information

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

Distance between Chicago and Boston is 1370 miles. Time difference between the cities is 1h. Airplanes depart 05:25 to 17:24 from 7 Chicago airports and arrive 05:25 to 17:24 to 4 Boston airports. Average flight time is 2h 16m.

  • The fastest flight 2h 14m
  • Average flight time 2h 16m
  • The earliest flight 05:25
  • The latest flight 17:24
  • Distance 852 ml

The cheapest months to travel to Boston are december (from 214 $), december (from 244 $).

What is the lowest airfare Chicago to Boston?

The cheapest plane ticket found by our users is $214. This airfare is for economy class on one-way AA2264 flight by American Airlines for December 4, 2022 which leaves O'Hare International in Chicago at 10:40 am and arrives at Boston Logan at 13:56.

Economy class
$214
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Business class
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First class
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Popular Airlines on the Route

The flight Chicago — Boston is served by 2 regular airlines and 1 low-cost airline. Most of the flights on this route are operated by American Airlines - 4 departures per week at the price of from $ 214 . And the most expensive tickets are offered by American Airlines airline - from $ 377.

Direct flights

There are 3 nonstop flights on the route. The fastest direct flight is B64312 by JetBlue takes 2h 14m and the cheapest is AA2264 by American Airlines for $214.

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Connecting Flights

There are 3 flights with layovers on the route. The fastest connecting flight is AA1784 by American Airlines takes 5h 18m and the cheapest is AA2264 by American Airlines for $265.

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Airports

You can fly from Chicago to Boston from 7 airports (O'Hare International, Midway, Dupage County, Chicago FSS, Merrill C Meigs (closed), Pal-Waukee, Chicago NAS).

Chicago airports

  • O'Hare International-ORD
    from $214
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  • Midway-MDW
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  • Dupage County-DPA
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  • Chicago FSS-CHI
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  • Merrill C Meigs (closed)-CGX
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  • Pal-Waukee-PWK
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  • Chicago NAS-NOH
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Boston airports

  • Boston City Heliport-JBC
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  • Boston RT128 Rail-ZRU
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  • Boston South Rail-ZTO
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  • Logan-BOS
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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.

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