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 december: one-way - $36, two-way – $62.
Direct flights
  • Check to choose departure date Check to choose departure date
Check prices for return flight
Find flights
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
Find flight
from$81
1:07 pm — 4:29 pm
1:07 pm — 4:29 pm AA834 American Airlines
Chicago — Boston
2h 22m
Find flight
from$81
3:11 pm — 6:36 pm
3:11 pm — 6:36 pm AA2321 American Airlines
Chicago — Boston
2h 25m
Find flight
from$128
5:19 pm — 8:45 pm
5:19 pm — 8:45 pm AA1251 American Airlines
Chicago — Boston
2h 26m
Find flight
from$163
6:35 pm — 9:58 pm
6:35 pm — 9:58 pm AA1172 American Airlines
Chicago — Boston
2h 23m
Find flight
from$36
7:15 am — 10:32 am
7:15 am — 10:32 am AA2384 American Airlines
Chicago — Boston
2h 17m
Find flight
from$36
8:45 am — 12:05 pm
8:45 am — 12:05 pm AA2723 American Airlines
Chicago — Boston
2h 20m
Find flight
from$36
9:50 am — 1:06 pm
9:50 am — 1:06 pm AA2264 American Airlines
Chicago — Boston
2h 16m
Find flight
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
Find flight
from$101
11:44 am — 0:21 am
+1 day
11:44 am — 2:59 pm AA18 American Airlines
Chicago — New York
8h 1m stop
11:00 pm — 0:21 am AA1278 American Airlines
New York — Boston
11h 37m
including layover
Find flight
from$162
12:30 pm — 8:21 pm
12:30 pm — 3:39 pm AA358 American Airlines
Chicago — New York
3h 21m stop
7:00 pm — 8:21 pm AA2122 American Airlines
New York — Boston
6h 51m
including layover
Find flight
from$175
1:45 pm — 10:12 pm
1:45 pm — 4:53 pm AA2817 American Airlines
Chicago — Charlotte
3h 4m stop
7:57 pm — 10:12 pm AA1843 American Airlines
Charlotte — Boston
7h 27m
including layover
Find flight
from$174
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
Find flight
from$157
3:22 pm — 11:35 pm
3:22 pm — 6:18 pm AA1015 American Airlines
Chicago — Washington D.C.
3h 42m stop
10:00 pm — 11:35 pm AA2138 American Airlines
Washington D.C. — Boston
7h 13m
including layover
Find flight
from$182
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
Find flight
from$174
5:25 am — 12:10 pm
5:25 am — 8:24 am AA1784 American Airlines
Chicago — Charlotte
1h 21m stop
9:45 am — 12:10 pm AA1902 American Airlines
Charlotte — Boston
5h 45m
including layover
Find flight
from$99
6:00 am — 2:24 pm
6:00 am — 9:07 am AA129 American Airlines
Chicago — New York
3h 53m stop
1:00 pm — 2:24 pm AA2131 American Airlines
New York — Boston
7h 24m
including layover
Find flight
from$100
7:00 am — 12:08 pm
7:00 am — 9:59 am AA1854 American Airlines
Chicago — Philadelphia
36m stop
10:35 am — 12:08 pm AA1153 American Airlines
Philadelphia — Boston
4h 8m
including layover
Find flight
from$100
8:06 am — 3:10 pm
8:06 am — 11:00 am AA985 American Airlines
Chicago — Washington D.C.
2h 30m stop
1:30 pm — 3:10 pm AA2119 American Airlines
Washington D.C. — Boston
6h 4m
including layover
Find flight
from$100
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
Find flight
from$221
*Departure and arrival times are local. Last updated on 12/05/2020

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 22m
  • The earliest flight 10:00 pm
  • The latest flight 9:55 pm
  • Distance 852 ml

The cheapest months for traveling to Boston are december (from 36 $), october (from 36 $), august (from 36 $).

The most expensive and popular months are september (from 38 $), august (from 36 $), october (from 36 $).

The cheapest flight by American Airlines that our users were able to find is $36. This airfare is economy class on one-way AA2384 flight for December 9, 2020 leaving O'Hare International in Chicago at 7:15 am, it includes all taxes and additional fees.

Find same flight?

Other Popular Airlines on the Route

Besides American Airlines there are other 1 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 15 direct flights every day from Chicago. Airlines and fares are below:

See more direct flights

Connecting Flights

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

See more connecting flights

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.

Back