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 $36 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 may: one-way - $36, two-way – $62.
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Below is a detailed 2021 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
10:40 am — 2:01 pm
10:40 am — 2:01 pm AA841 American Airlines
Chicago — Boston
2h 21m
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from$82
12:00 pm — 3:17 pm
12:00 pm — 3:17 pm AA832 American Airlines
Chicago — Boston
2h 17m
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from$37
1:15 pm — 4:41 pm
1:15 pm — 4:41 pm AA1162 American Airlines
Chicago — Boston
2h 26m
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from$38
2:55 pm — 6:20 pm
2:55 pm — 6:20 pm AA2321 American Airlines
Chicago — Boston
2h 25m
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from$36
3:11 pm — 6:36 pm
3:11 pm — 6:36 pm AA2321 American Airlines
Chicago — Boston
2h 25m
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from$129
5:00 pm — 8:21 pm
5:00 pm — 8:21 pm AA836 American Airlines
Chicago — Boston
2h 21m
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from$37
6:00 am — 9:16 am
6:00 am — 9:16 am AA798 American Airlines
Chicago — Boston
2h 16m
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from$37
7:30 pm — 10:53 pm
7:30 pm — 10:53 pm AA2682 American Airlines
Chicago — Boston
2h 23m
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from$36
8:20 am — 11:44 am
8:20 am — 11:44 am AA990 American Airlines
Chicago — Boston
2h 24m
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from$36
9:55 am — 1:18 pm
9:55 am — 1:18 pm AA2883 American Airlines
Chicago — Boston
2h 23m
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from$36
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$102
11:55 am — 5:15 pm
11:55 am — 2:35 pm AA2401 American Airlines
Chicago — Washington D.C.
55m stop
3:30 pm — 5:15 pm AA2148 American Airlines
Washington D.C. — Boston
4h 20m
including layover
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from$58
12:00 pm — 5:02 pm
12:00 pm — 3:00 pm AA2095 American Airlines
Chicago — Philadelphia
30m stop
3:30 pm — 5:02 pm AA809 American Airlines
Philadelphia — Boston
4h 2m
including layover
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from$58
1:35 pm — 7:13 pm
1:35 pm — 4:40 pm AA493 American Airlines
Chicago — Philadelphia
55m stop
5:35 pm — 7:13 pm AA2427 American Airlines
Philadelphia — Boston
4h 38m
including layover
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from$58
2:17 pm — 0:21 am
+1 day
2:17 pm — 5:39 pm AA178 American Airlines
Chicago — New York
5h 21m stop
11:00 pm — 0:21 am AA1278 American Airlines
New York — Boston
9h 4m
including layover
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from$158
3:20 pm — 8:22 pm
3:20 pm — 6:00 pm AA2462 American Airlines
Chicago — Washington D.C.
30m stop
6:30 pm — 8:22 pm AA2134 American Airlines
Washington D.C. — Boston
4h 2m
including layover
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from$58
4:41 pm — 10:34 pm
4:41 pm — 7:51 pm AA2853 American Airlines
Chicago — Philadelphia
1h 9m stop
9:00 pm — 10:34 pm AA2618 American Airlines
Philadelphia — Boston
4h 53m
including layover
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from$58
5:45 am — 12:16 pm
5:45 am — 8:41 am AA1784 American Airlines
Chicago — Charlotte
1h 14m stop
9:55 am — 12:16 pm AA1902 American Airlines
Charlotte — Boston
5h 31m
including layover
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from$56
6:35 pm — 11:29 pm
6:35 pm — 9:15 pm AA878 American Airlines
Chicago — Washington D.C.
45m stop
10:00 pm — 11:29 pm AA2138 American Airlines
Washington D.C. — Boston
3h 54m
including layover
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from$58
7:15 am — 12:38 pm
7:15 am — 10:15 am AA1666 American Airlines
Chicago — Philadelphia
45m stop
11:00 am — 12:38 pm AA4439 American Airlines
Philadelphia — Boston
4h 23m
including layover
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from$62
8:20 am — 1:01 pm
8:20 am — 11:00 am AA985 American Airlines
Chicago — Washington D.C.
30m stop
11:30 am — 1:01 pm AA2170 American Airlines
Washington D.C. — Boston
3h 41m
including layover
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from$58
9:55 am — 6:20 pm
9:55 am — 11:06 am AA2913 American Airlines
Chicago — Lake Saint Louis
1h 1m stop
12:07 pm — 3:31 pm AA4416 American Airlines
Lake Saint Louis — New York
1h 29m stop
5:00 pm — 6:20 pm AA2141 American Airlines
New York — Boston
7h 25m
including layover
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from$224
*Departure and arrival times are local. Last updated on 05/13/2021

Flight Information

There are 32 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 21m
  • The earliest flight 10:00 pm
  • The latest flight 9:55 pm
  • Distance 852 ml

The cheapest months for traveling to Boston are september (from 36 $), november (from 37 $), october (from 37 $).

The most expensive and popular months are august (from 58 $), october (from 37 $), november (from 37 $).

The cheapest flight by American Airlines that our users were able to find is $36. This airfare is economy class on one-way AA2682 flight for September 18, 2020 leaving O'Hare International in Chicago at 7:30 pm, 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 103 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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