American Airlines Chicago to Boston Flights

Return flight: Boston – Chicago

Cheapflightsplus.com will find cheap American Airlines flights from Chicago to Boston. Compare airline ticket prices and book air tickets starting from $38 from trusted online travel agencies, web sites and directly from airlines. Check flights schedule of American Airlines, arrivals and departure details below.

Find Cheap Airfare Chicago (IL) — Boston (MA) by American Airlines

To find cheap tickets choose a day of your departure with attractive price on the graph below and click «Find flights». For round trip flights please click «Check prices for return flight». The cheapest airfare is in august: one-way - $38, two-way – $65.
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Below is a detailed 2020 flight schedule for today, tomorrow and all other days. It may vary depending on season and a day of the week of your desired trip. We recommend booking your itinerary at least 2 weeks prior your travel to get the best price and availability by the airline.
Departure Arrival Flight Details Flight Time Price
10:15 am — 1:46 pm
10:15 am — 1:46 pm AA2723 American Airlines
Chicago — Boston
2h 31m
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from$38
1:07 pm — 4:29 pm
1:07 pm — 4:29 pm AA834 American Airlines
Chicago — Boston
2h 22m
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from$86
3:15 pm — 6:46 pm
3:15 pm — 6:46 pm AA1172 American Airlines
Chicago — Boston
2h 31m
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from$38
5:19 pm — 8:45 pm
5:19 pm — 8:45 pm AA1251 American Airlines
Chicago — Boston
2h 26m
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from$173
6:45 pm — 10:17 pm
6:45 pm — 10:17 pm AA2384 American Airlines
Chicago — Boston
2h 32m
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from$38
7:10 am — 10:31 am
7:10 am — 10:31 am AA2384 American Airlines
Chicago — Boston
2h 21m
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from$81
8:20 am — 11:45 am
8:20 am — 11:45 am AA2264 American Airlines
Chicago — Boston
2h 25m
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from$38
9:55 pm — 1:11 am
+1 day
9:55 pm — 1:11 am AA1399 American Airlines
Chicago — Boston
2h 16m
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from$81
10:25 am — 5:26 pm
10:25 am — 1:29 pm AA1668 American Airlines
Chicago — Charlotte
1h 38m stop
3:07 pm — 5:26 pm AA2687 American Airlines
Charlotte — Boston
6h 1m
including layover
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from$107
11:15 am — 6:31 pm
11:15 am — 2:14 pm AA2588 American Airlines
Chicago — Philadelphia
2h 46m stop
5:00 pm — 6:31 pm AA2713 American Airlines
Philadelphia — Boston
6h 16m
including layover
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from$59
12:04 pm — 6:06 pm
12:04 pm — 3:04 pm AA2372 American Airlines
Chicago — Charlotte
51m stop
3:55 pm — 6:06 pm AA1728 American Airlines
Charlotte — Boston
5h 2m
including layover
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from$57
1:36 pm — 8:33 pm
1:36 pm — 4:49 pm AA1920 American Airlines
Chicago — Philadelphia
2h 6m stop
6:55 pm — 8:33 pm AA2475 American Airlines
Philadelphia — Boston
5h 57m
including layover
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from$59
2:02 pm — 8:19 pm
2:02 pm — 5:04 pm AA2817 American Airlines
Chicago — Charlotte
59m stop
6:03 pm — 8:19 pm AA1937 American Airlines
Charlotte — Boston
5h 17m
including layover
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from$57
3:36 pm — 10:04 pm
3:36 pm — 6:37 pm AA815 American Airlines
Chicago — Charlotte
1h 19m stop
7:56 pm — 10:04 pm AA1978 American Airlines
Charlotte — Boston
5h 28m
including layover
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from$57
4:11 pm — 0:28 am
+1 day
4:11 pm — 7:09 pm AA583 American Airlines
Chicago — Charlotte
3h 6m stop
10:15 pm — 0:28 am AA1937 American Airlines
Charlotte — Boston
7h 17m
including layover
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from$185
5:20 am — 11:56 am
5:20 am — 8:13 am AA1784 American Airlines
Chicago — Charlotte
1h 27m stop
9:40 am — 11:56 am AA1902 American Airlines
Charlotte — Boston
5h 36m
including layover
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from$58
6:30 am — 11:27 am
6:30 am — 9:27 am AA2537 American Airlines
Chicago — Philadelphia
33m stop
10:00 am — 11:27 am AA2663 American Airlines
Philadelphia — Boston
3h 57m
including layover
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from$59
7:19 am — 3:36 pm
7:19 am — 10:18 am AA2052 American Airlines
Chicago — Charlotte
3h 5m stop
1:23 pm — 3:36 pm AA471 American Airlines
Charlotte — Boston
7h 17m
including layover
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from$57
8:53 am — 5:04 pm
8:53 am — 11:45 am AA1002 American Airlines
Chicago — Washington D.C.
3h 45m stop
3:30 pm — 5:04 pm AA2138 American Airlines
Washington D.C. — Boston
7h 11m
including layover
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from$59
9:28 am — 5:07 pm
9:28 am — 12:24 pm AA2895 American Airlines
Chicago — Charlotte
2h 27m stop
2:51 pm — 5:07 pm AA955 American Airlines
Charlotte — Boston
6h 39m
including layover
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from$57
*Departure and arrival times are local. Last updated on 08/14/2020

Flight Information

There are 14 flights by American Airlines from Chicago to Boston every week with departures from Chicago FSS, Midway, O'Hare International, Chicago NAS, Merrill C Meigs (closed), Dupage County, Pal-Waukee. All flights arrive at Logan, Boston City Heliport, Boston RT128 Rail, Boston South Rail.

Departures start from 10:00 pm to 9:55 pm. Nonstop flight is 2h 16m. The time difference between Chicago and Boston is 1h.

  • The fastest flight 2h 16m
  • Average flight time 2h 24m
  • The earliest flight 10:00 pm
  • The latest flight 9:55 pm
  • Distance 852 ml

The cheapest months for traveling to Boston are august (from 38 $), june (from 47 $), october (from 81 $).

The most expensive and popular months are july (from 88 $), october (from 81 $), june (from 47 $).

The cheapest flight by American Airlines that our users were able to find is $38. This airfare is economy class on one-way AA2264 flight for August 8, 2020 leaving O'Hare International in Chicago at 8:20 am, it includes all taxes and additional fees.

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Other Popular Airlines on the Route

Besides American Airlines there are other 7 airline carriers between Chicago and Boston. Please review schedules and prices from the most popular airlines to find the best airfare deals from Chicago to Boston.

Nonstop flights

There are 26 direct flights every day from Chicago. Airlines and fares are below:

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Connecting Flights

List of flights with layovers (1 and more stops):

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How to book an air 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 airfare.
  • 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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