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 $53 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 - $53, two-way – $91.
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Find flights
Below is a detailed 2019 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
10:05 am — 1:19 pm
10:05 am — 1:19 pm AA2264 American Airlines
Chicago — Boston
2h 14m
Find flight
from$64
10:05 pm — 1:21 am
+1 day
10:05 pm — 1:21 am AA848 American Airlines
Chicago — Boston
2h 16m
Find flight
from$99
11:58 am — 3:17 pm
11:58 am — 3:17 pm AA2312 American Airlines
Chicago — Boston
2h 19m
Find flight
from$140
1:20 pm — 4:36 pm
1:20 pm — 4:36 pm AA1360 American Airlines
Chicago — Boston
2h 16m
Find flight
from$176
1:31 pm — 4:43 pm
1:31 pm — 4:43 pm AA1360 American Airlines
Chicago — Boston
2h 12m
Find flight
from$95
3:05 pm — 6:26 pm
3:05 pm — 6:26 pm AA2321 American Airlines
Chicago — Boston
2h 21m
Find flight
from$140
4:55 pm — 8:07 pm
4:55 pm — 8:07 pm AA1251 American Airlines
Chicago — Boston
2h 12m
Find flight
from$64
6:05 am — 9:23 am
6:05 am — 9:23 am AA140 American Airlines
Chicago — Boston
2h 18m
Find flight
from$99
6:29 pm — 9:49 pm
6:29 pm — 9:49 pm AA1172 American Airlines
Chicago — Boston
2h 20m
Find flight
from$211
6:34 pm — 9:50 pm
6:34 pm — 9:50 pm AA1172 American Airlines
Chicago — Boston
2h 16m
Find flight
from$104
7:15 am — 10:26 am
7:15 am — 10:26 am AA2384 American Airlines
Chicago — Boston
2h 11m
Find flight
from$53
8:21 pm — 11:32 pm
8:21 pm — 11:32 pm AA2682 American Airlines
Chicago — Boston
2h 11m
Find flight
from$64
8:45 am — 11:58 am
8:45 am — 11:58 am AA2723 American Airlines
Chicago — Boston
2h 13m
Find flight
from$64
10:30 am — 6:16 pm
10:30 am — 1:38 pm AA114 American Airlines
Chicago — New York
3h 22m stop
5:00 pm — 6:16 pm AA2141 American Airlines
New York — Boston
6h 46m
including layover
Find flight
from$253
10:30 am — 4:11 pm
10:30 am — 1:38 pm AA114 American Airlines
Chicago — New York
1h 22m stop
3:00 pm — 4:11 pm AA2172 American Airlines
New York — Boston
4h 41m
including layover
Find flight
from$253
10:30 am — 5:16 pm
10:30 am — 1:38 pm AA114 American Airlines
Chicago — New York
2h 22m stop
4:00 pm — 5:16 pm AA2128 American Airlines
New York — Boston
5h 46m
including layover
Find flight
from$253
10:30 am — 7:18 pm
10:30 am — 1:38 pm AA114 American Airlines
Chicago — New York
4h 22m stop
6:00 pm — 7:18 pm AA2151 American Airlines
New York — Boston
7h 48m
including layover
Find flight
from$313
10:30 am — 8:17 pm
10:30 am — 1:38 pm AA114 American Airlines
Chicago — New York
5h 22m stop
7:00 pm — 8:17 pm AA2122 American Airlines
New York — Boston
8h 47m
including layover
Find flight
from$356
10:35 am — 5:13 pm
10:35 am — 1:33 pm AA1668 American Airlines
Chicago — Charlotte
1h 21m stop
2:54 pm — 5:13 pm AA2348 American Airlines
Charlotte — Boston
5h 38m
including layover
Find flight
from$260
10:35 am — 6:46 pm
10:35 am — 1:33 pm AA1668 American Airlines
Chicago — Charlotte
2h 56m stop
4:29 pm — 6:46 pm AA1728 American Airlines
Charlotte — Boston
7h 11m
including layover
Find flight
from$260
10:35 am — 5:19 pm
10:35 am — 1:36 pm AA1668 American Airlines
Chicago — Charlotte
1h 24m stop
3:00 pm — 5:19 pm AA2801 American Airlines
Charlotte — Boston
5h 44m
including layover
Find flight
from$260
10:40 am — 5:11 pm
10:40 am — 1:37 pm AA1668 American Airlines
Chicago — Charlotte
1h 23m stop
3:00 pm — 5:11 pm AA2801 American Airlines
Charlotte — Boston
5h 31m
including layover
Find flight
from$250
11:15 am — 7:29 pm
11:15 am — 1:37 pm AA2223 American Airlines
Chicago — Dallas
1h 8m stop
2:45 pm — 7:29 pm AA2579 American Airlines
Dallas — Boston
7h 14m
including layover
Find flight
from$571
11:45 am — 6:28 pm
11:45 am — 2:30 pm AA3556 American Airlines
Chicago — Harrisburg
2h 30m stop
5:00 pm — 6:28 pm AA4893 American Airlines
Harrisburg — Boston
5h 43m
including layover
Find flight
from$1080
11:50 am — 4:40 pm
11:50 am — 2:45 pm AA1899 American Airlines
Chicago — Philadelphia
30m stop
3:15 pm — 4:40 pm AA1776 American Airlines
Philadelphia — Boston
3h 50m
including layover
Find flight
from$414
11:50 am — 7:23 pm
11:50 am — 2:45 pm AA1899 American Airlines
Chicago — Philadelphia
3h 4m stop
5:49 pm — 7:23 pm AA688 American Airlines
Philadelphia — Boston
6h 33m
including layover
Find flight
from$414
11:50 am — 8:53 pm
11:50 am — 2:48 pm AA1899 American Airlines
Chicago — Philadelphia
4h 37m stop
7:25 pm — 8:53 pm AA1856 American Airlines
Philadelphia — Boston
8h 3m
including layover
Find flight
from$492
11:55 am — 6:55 pm
11:55 am — 2:31 pm AA3686 American Airlines
Chicago — Rochester
3h 4m stop
5:35 pm — 6:55 pm AA3761 American Airlines
Rochester — Boston
6h
including layover
Find flight
from$458
12:00 pm — 0:49 am
+1 day
12:00 pm — 4:05 pm AA335 American Airlines
Chicago — Miami
5h 30m stop
9:35 pm — 0:49 am AA1074 American Airlines
Miami — Boston
11h 49m
including layover
Find flight
from$283
12:05 pm — 6:15 pm
12:05 pm — 2:40 pm AA3328 American Airlines
Chicago — Pittsburgh
1h 49m stop
4:29 pm — 6:15 pm AA3756 American Airlines
Pittsburgh — Boston
5h 10m
including layover
Find flight
from$330
12:15 pm — 10:29 pm
12:15 pm — 3:35 pm AA272 American Airlines
Chicago — New York
5h 35m stop
9:10 pm — 10:29 pm AA1278 American Airlines
New York — Boston
9h 14m
including layover
Find flight
from$275
12:20 pm — 6:03 pm
12:20 pm — 3:18 pm AA2296 American Airlines
Chicago — Washington D.C.
1h 12m stop
4:30 pm — 6:03 pm AA2120 American Airlines
Washington D.C. — Boston
4h 43m
including layover
Find flight
from$349
12:23 pm — 6:00 pm
12:23 pm — 3:18 pm AA2296 American Airlines
Chicago — Washington D.C.
1h 12m stop
4:30 pm — 6:00 pm AA2120 American Airlines
Washington D.C. — Boston
4h 37m
including layover
Find flight
from$252
12:30 pm — 6:16 pm
12:30 pm — 3:39 pm AA381 American Airlines
Chicago — New York
1h 21m stop
5:00 pm — 6:16 pm AA2141 American Airlines
New York — Boston
4h 46m
including layover
Find flight
from$253
12:30 pm — 8:49 pm
12:30 pm — 3:33 pm AA2080 American Airlines
Chicago — Charlotte
2h 57m stop
6:30 pm — 8:49 pm AA1978 American Airlines
Charlotte — Boston
7h 19m
including layover
Find flight
from$260
12:30 pm — 9:16 pm
12:30 pm — 3:39 pm AA381 American Airlines
Chicago — New York
4h 21m stop
8:00 pm — 9:16 pm AA2147 American Airlines
New York — Boston
7h 46m
including layover
Find flight
from$291
12:30 pm — 7:18 pm
12:30 pm — 3:40 pm AA381 American Airlines
Chicago — New York
2h 20m stop
6:00 pm — 7:18 pm AA2151 American Airlines
New York — Boston
5h 48m
including layover
Find flight
from$307
12:31 pm — 7:00 pm
12:31 pm — 3:30 pm AA2080 American Airlines
Chicago — Charlotte
1h 9m stop
4:39 pm — 7:00 pm AA1728 American Airlines
Charlotte — Boston
5h 29m
including layover
Find flight
from$347
12:45 pm — 7:11 pm
12:45 pm — 3:42 pm AA3821 American Airlines
Chicago — Albany
2h 26m stop
6:08 pm — 7:11 pm 9K1816 Cape Air
Albany — Boston
5h 26m
including layover
Find flight
from$482
1:30 pm — 0:55 am
+1 day
1:30 pm — 5:42 pm AA2796 American Airlines
Chicago — Miami
3h 53m stop
9:35 pm — 0:55 am AA1054 American Airlines
Miami — Boston
10h 25m
including layover
Find flight
from$256
1:30 pm — 7:18 pm
1:30 pm — 4:40 pm AA2302 American Airlines
Chicago — New York
1h 20m stop
6:00 pm — 7:18 pm AA2151 American Airlines
New York — Boston
4h 48m
including layover
Find flight
from$261
1:30 pm — 8:17 pm
1:30 pm — 4:40 pm AA2302 American Airlines
Chicago — New York
2h 20m stop
7:00 pm — 8:17 pm AA2122 American Airlines
New York — Boston
5h 47m
including layover
Find flight
from$307
1:30 pm — 8:06 pm
1:30 pm — 4:29 pm AA1486 American Airlines
Chicago — Washington D.C.
2h 1m stop
6:30 pm — 8:06 pm AA2134 American Airlines
Washington D.C. — Boston
5h 36m
including layover
Find flight
from$349
1:31 pm — 8:06 pm
1:31 pm — 4:29 pm AA1486 American Airlines
Chicago — Washington D.C.
2h 1m stop
6:30 pm — 8:06 pm AA2144 American Airlines
Washington D.C. — Boston
5h 35m
including layover
Find flight
from$349
1:31 pm — 7:09 pm
1:31 pm — 4:29 pm AA1486 American Airlines
Chicago — Washington D.C.
1h 1m stop
5:30 pm — 7:09 pm AA2116 American Airlines
Washington D.C. — Boston
4h 38m
including layover
Find flight
from$349
1:36 pm — 7:23 pm
1:36 pm — 4:44 pm AA2095 American Airlines
Chicago — Philadelphia
1h 5m stop
5:49 pm — 7:23 pm AA688 American Airlines
Philadelphia — Boston
4h 47m
including layover
Find flight
from$414
1:37 pm — 7:07 pm
1:37 pm — 4:29 pm AA1486 American Airlines
Chicago — Washington D.C.
1h 1m stop
5:30 pm — 7:07 pm AA2116 American Airlines
Washington D.C. — Boston
4h 30m
including layover
Find flight
from$256
1:37 pm — 7:08 pm
1:37 pm — 4:29 pm AA1486 American Airlines
Chicago — Washington D.C.
1h 1m stop
5:30 pm — 7:08 pm AA4763 American Airlines
Washington D.C. — Boston
4h 31m
including layover
Find flight
from$336
1:45 pm — 8:49 pm
1:45 pm — 4:47 pm AA864 American Airlines
Chicago — Charlotte
1h 43m stop
6:30 pm — 8:49 pm AA1978 American Airlines
Charlotte — Boston
6h 4m
including layover
Find flight
from$260
2:05 pm — 10:44 pm
2:05 pm — 5:08 pm AA864 American Airlines
Chicago — Charlotte
3h 26m stop
8:34 pm — 10:44 pm AA2598 American Airlines
Charlotte — Boston
7h 39m
including layover
Find flight
from$260
2:05 pm — 0:16 am
+1 day
2:05 pm — 5:08 pm AA864 American Airlines
Chicago — Charlotte
5h 1m stop
10:09 pm — 0:16 am AA1937 American Airlines
Charlotte — Boston
9h 11m
including layover
Find flight
from$442
2:23 pm — 11:06 pm
2:23 pm — 4:50 pm AA2346 American Airlines
Chicago — Dallas
1h 35m stop
6:25 pm — 11:06 pm AA1483 American Airlines
Dallas — Boston
7h 43m
including layover
Find flight
from$481
2:30 pm — 9:16 pm
2:30 pm — 5:40 pm AA380 American Airlines
Chicago — New York
2h 20m stop
8:00 pm — 9:16 pm AA2147 American Airlines
New York — Boston
5h 46m
including layover
Find flight
from$285
2:30 pm — 8:17 pm
2:30 pm — 5:40 pm AA380 American Airlines
Chicago — New York
1h 20m stop
7:00 pm — 8:17 pm AA2122 American Airlines
New York — Boston
4h 47m
including layover
Find flight
from$307
3:10 pm — 11:30 pm
3:10 pm — 6:04 pm AA2679 American Airlines
Chicago — Washington D.C.
3h 56m stop
10:00 pm — 11:30 pm AA2138 American Airlines
Washington D.C. — Boston
7h 20m
including layover
Find flight
from$261
3:10 pm — 9:04 pm
3:10 pm — 6:02 pm AA2679 American Airlines
Chicago — Washington D.C.
1h 28m stop
7:30 pm — 9:04 pm AA2140 American Airlines
Washington D.C. — Boston
4h 54m
including layover
Find flight
from$349
3:11 pm — 8:53 pm
3:11 pm — 6:15 pm AA2011 American Airlines
Chicago — Philadelphia
1h 10m stop
7:25 pm — 8:53 pm AA1856 American Airlines
Philadelphia — Boston
4h 42m
including layover
Find flight
from$349
3:11 pm — 8:54 pm
3:11 pm — 6:14 pm AA1920 American Airlines
Chicago — Philadelphia
1h 11m stop
7:25 pm — 8:54 pm AA1856 American Airlines
Philadelphia — Boston
4h 43m
including layover
Find flight
from$414
3:30 pm — 9:16 pm
3:30 pm — 6:38 pm AA325 American Airlines
Chicago — New York
1h 22m stop
8:00 pm — 9:16 pm AA2147 American Airlines
New York — Boston
4h 46m
including layover
Find flight
from$285
3:46 pm — 0:16 am
+1 day
3:46 pm — 6:47 pm AA1195 American Airlines
Chicago — Charlotte
3h 22m stop
10:09 pm — 0:16 am AA1937 American Airlines
Charlotte — Boston
7h 30m
including layover
Find flight
from$260
3:46 pm — 10:44 pm
3:46 pm — 6:46 pm AA2467 American Airlines
Chicago — Charlotte
1h 48m stop
8:34 pm — 10:44 pm AA1843 American Airlines
Charlotte — Boston
5h 58m
including layover
Find flight
from$260
4:40 pm — 10:50 pm
4:40 pm — 7:41 pm AA1941 American Airlines
Chicago — Philadelphia
1h 44m stop
9:25 pm — 10:50 pm AA1874 American Airlines
Philadelphia — Boston
5h 10m
including layover
Find flight
from$405
4:42 pm — 0:55 am
+1 day
4:42 pm — 8:48 pm AA160 American Airlines
Chicago — Miami
47m stop
9:35 pm — 0:55 am AA1054 American Airlines
Miami — Boston
7h 13m
including layover
Find flight
from$283
4:45 pm — 0:49 am
+1 day
4:45 pm — 8:50 pm AA160 American Airlines
Chicago — Miami
45m stop
9:35 pm — 0:49 am AA1074 American Airlines
Miami — Boston
7h 4m
including layover
Find flight
from$389
4:55 pm — 0:54 am
+1 day
4:55 pm — 7:25 pm AA2501 American Airlines
Chicago — Dallas
55m stop
8:20 pm — 0:54 am AA1456 American Airlines
Dallas — Boston
6h 59m
including layover
Find flight
from$594
4:58 pm — 10:44 pm
4:58 pm — 7:55 pm AA1883 American Airlines
Chicago — Charlotte
39m stop
8:34 pm — 10:44 pm AA2598 American Airlines
Charlotte — Boston
4h 46m
including layover
Find flight
from$260
5:02 pm — 10:44 pm
5:02 pm — 8:00 pm AA1883 American Airlines
Chicago — Charlotte
34m stop
8:34 pm — 10:44 pm AA1843 American Airlines
Charlotte — Boston
4h 42m
including layover
Find flight
from$260
5:02 pm — 0:16 am
+1 day
5:02 pm — 8:00 pm AA1883 American Airlines
Chicago — Charlotte
2h 9m stop
10:09 pm — 0:16 am AA1937 American Airlines
Charlotte — Boston
6h 14m
including layover
Find flight
from$260
5:06 pm — 10:30 pm
5:06 pm — 8:04 pm AA2499 American Airlines
Chicago — Washington D.C.
56m stop
9:00 pm — 10:30 pm AA2150 American Airlines
Washington D.C. — Boston
4h 24m
including layover
Find flight
from$349
5:06 pm — 11:30 pm
5:06 pm — 8:04 pm AA2499 American Airlines
Chicago — Washington D.C.
1h 56m stop
10:00 pm — 11:30 pm AA2138 American Airlines
Washington D.C. — Boston
5h 24m
including layover
Find flight
from$349
5:08 pm — 10:27 pm
5:08 pm — 8:00 pm AA2499 American Airlines
Chicago — Washington D.C.
1h stop
9:00 pm — 10:27 pm AA2150 American Airlines
Washington D.C. — Boston
4h 19m
including layover
Find flight
from$256
5:15 am — 1:55 pm
5:15 am — 7:40 am AA2429 American Airlines
Chicago — Dallas
1h 30m stop
9:10 am — 1:55 pm AA1497 American Airlines
Dallas — Boston
7h 40m
including layover
Find flight
from$481
5:15 am — 1:57 pm
5:15 am — 7:33 am AA328 American Airlines
Chicago — Dallas
1h 37m stop
9:10 am — 1:57 pm AA1497 American Airlines
Dallas — Boston
7h 42m
including layover
Find flight
from$481
5:25 am — 12:12 pm
5:25 am — 8:22 am AA2215 American Airlines
Chicago — Philadelphia
2h 23m stop
10:45 am — 12:12 pm AA689 American Airlines
Philadelphia — Boston
5h 47m
including layover
Find flight
from$252
5:25 am — 12:35 pm
5:25 am — 8:22 am AA2215 American Airlines
Chicago — Philadelphia
2h 53m stop
11:15 am — 12:35 pm AA1898 American Airlines
Philadelphia — Boston
6h 10m
including layover
Find flight
from$252
5:25 am — 12:36 pm
5:25 am — 8:23 am AA2215 American Airlines
Chicago — Philadelphia
2h 52m stop
11:15 am — 12:36 pm AA826 American Airlines
Philadelphia — Boston
6h 11m
including layover
Find flight
from$261
5:25 am — 10:50 am
5:25 am — 8:23 am AA2215 American Airlines
Chicago — Philadelphia
1h 2m stop
9:25 am — 10:50 am AA1134 American Airlines
Philadelphia — Boston
4h 25m
including layover
Find flight
from$261
5:49 am — 12:21 pm
5:49 am — 8:43 am AA2523 American Airlines
Chicago — Charlotte
1h 22m stop
10:05 am — 12:21 pm AA1320 American Airlines
Charlotte — Boston
5h 32m
including layover
Find flight
from$250
5:49 am — 1:31 pm
5:49 am — 8:43 am AA2523 American Airlines
Chicago — Charlotte
2h 41m stop
11:24 am — 1:31 pm AA452 American Airlines
Charlotte — Boston
6h 42m
including layover
Find flight
from$250
5:49 am — 1:48 pm
5:49 am — 8:42 am AA2523 American Airlines
Chicago — Charlotte
2h 52m stop
11:34 am — 1:48 pm AA410 American Airlines
Charlotte — Boston
6h 59m
including layover
Find flight
from$260
6:00 am — 11:23 am
6:00 am — 9:10 am AA116 American Airlines
Chicago — New York
50m stop
10:00 am — 11:23 am AA2136 American Airlines
New York — Boston
4h 23m
including layover
Find flight
from$224
6:00 am — 12:22 pm
6:00 am — 9:10 am AA116 American Airlines
Chicago — New York
1h 50m stop
11:00 am — 12:22 pm AA2162 American Airlines
New York — Boston
5h 22m
including layover
Find flight
from$224
6:00 am — 1:16 pm
6:00 am — 9:10 am AA116 American Airlines
Chicago — New York
2h 50m stop
12:00 pm — 1:16 pm AA2161 American Airlines
New York — Boston
6h 16m
including layover
Find flight
from$224
6:00 am — 2:14 pm
6:00 am — 9:10 am AA116 American Airlines
Chicago — New York
3h 50m stop
1:00 pm — 2:14 pm AA2131 American Airlines
New York — Boston
7h 14m
including layover
Find flight
from$224
6:20 pm — 0:15 am
+1 day
6:20 pm — 9:14 pm AA354 American Airlines
Chicago — Charlotte
58m stop
10:12 pm — 0:15 am AA1937 American Airlines
Charlotte — Boston
4h 55m
including layover
Find flight
from$250
6:30 am — 12:22 pm
6:30 am — 9:40 am AA398 American Airlines
Chicago — New York
1h 20m stop
11:00 am — 12:22 pm AA2162 American Airlines
New York — Boston
4h 52m
including layover
Find flight
from$253
6:30 am — 2:14 pm
6:30 am — 9:40 am AA398 American Airlines
Chicago — New York
3h 20m stop
1:00 pm — 2:14 pm AA2131 American Airlines
New York — Boston
6h 44m
including layover
Find flight
from$253
6:30 am — 1:16 pm
6:30 am — 9:40 am AA398 American Airlines
Chicago — New York
2h 20m stop
12:00 pm — 1:16 pm AA2161 American Airlines
New York — Boston
5h 46m
including layover
Find flight
from$253
6:30 am — 3:14 pm
6:30 am — 10:37 am AA2498 American Airlines
Chicago — Miami
1h 23m stop
12:00 pm — 3:14 pm AA29 American Airlines
Miami — Boston
7h 44m
including layover
Find flight
from$256
7:00 am — 12:04 pm
7:00 am — 9:47 am AA2378 American Airlines
Chicago — Washington D.C.
43m stop
10:30 am — 12:04 pm AA2129 American Airlines
Washington D.C. — Boston
4h 4m
including layover
Find flight
from$252
7:00 am — 12:14 pm
7:00 am — 10:01 am AA1854 American Airlines
Chicago — Philadelphia
44m stop
10:45 am — 12:14 pm AA689 American Airlines
Philadelphia — Boston
4h 14m
including layover
Find flight
from$261
7:00 am — 12:36 pm
7:00 am — 9:58 am AA1854 American Airlines
Chicago — Philadelphia
1h 17m stop
11:15 am — 12:36 pm AA826 American Airlines
Philadelphia — Boston
4h 36m
including layover
Find flight
from$261
7:00 am — 12:59 pm
7:00 am — 9:53 am AA2378 American Airlines
Chicago — Washington D.C.
1h 37m stop
11:30 am — 12:59 pm AA2170 American Airlines
Washington D.C. — Boston
4h 59m
including layover
Find flight
from$349
7:00 am — 12:37 pm
7:00 am — 10:01 am AA1854 American Airlines
Chicago — Philadelphia
1h 14m stop
11:15 am — 12:37 pm AA1898 American Airlines
Philadelphia — Boston
4h 37m
including layover
Find flight
from$349
7:30 am — 1:16 pm
7:30 am — 10:40 am AA337 American Airlines
Chicago — New York
1h 20m stop
12:00 pm — 1:16 pm AA2161 American Airlines
New York — Boston
4h 46m
including layover
Find flight
from$253
7:30 am — 2:19 pm
7:30 am — 10:40 am AA337 American Airlines
Chicago — New York
2h 20m stop
1:00 pm — 2:19 pm AA2131 American Airlines
New York — Boston
5h 49m
including layover
Find flight
from$253
7:30 am — 3:14 pm
7:30 am — 10:40 am AA337 American Airlines
Chicago — New York
3h 20m stop
2:00 pm — 3:14 pm AA2146 American Airlines
New York — Boston
6h 44m
including layover
Find flight
from$253
7:30 am — 4:11 pm
7:30 am — 10:40 am AA337 American Airlines
Chicago — New York
4h 20m stop
3:00 pm — 4:11 pm AA2172 American Airlines
New York — Boston
7h 41m
including layover
Find flight
from$259
8:18 am — 1:52 pm
8:18 am — 11:08 am AA985 American Airlines
Chicago — Washington D.C.
1h 22m stop
12:30 pm — 1:52 pm AA2142 American Airlines
Washington D.C. — Boston
4h 34m
including layover
Find flight
from$252
8:20 am — 3:02 pm
8:20 am — 11:08 am AA985 American Airlines
Chicago — Washington D.C.
2h 22m stop
1:30 pm — 3:02 pm AA2119 American Airlines
Washington D.C. — Boston
5h 42m
including layover
Find flight
from$261
8:20 am — 2:00 pm
8:20 am — 11:10 am AA985 American Airlines
Chicago — Washington D.C.
1h 20m stop
12:30 pm — 2:00 pm AA2142 American Airlines
Washington D.C. — Boston
4h 40m
including layover
Find flight
from$349
8:30 am — 3:14 pm
8:30 am — 11:39 am AA367 American Airlines
Chicago — New York
2h 21m stop
2:00 pm — 3:14 pm AA2146 American Airlines
New York — Boston
5h 44m
including layover
Find flight
from$253
8:30 am — 2:19 pm
8:30 am — 11:39 am AA367 American Airlines
Chicago — New York
1h 21m stop
1:00 pm — 2:19 pm AA2131 American Airlines
New York — Boston
4h 49m
including layover
Find flight
from$253
8:30 am — 4:11 pm
8:30 am — 11:39 am AA367 American Airlines
Chicago — New York
3h 21m stop
3:00 pm — 4:11 pm AA2172 American Airlines
New York — Boston
6h 41m
including layover
Find flight
from$253
8:30 am — 5:16 pm
8:30 am — 11:39 am AA367 American Airlines
Chicago — New York
4h 21m stop
4:00 pm — 5:16 pm AA2128 American Airlines
New York — Boston
7h 46m
including layover
Find flight
from$259
8:30 am — 3:05 pm
8:30 am — 11:07 am AA3838 American Airlines
Chicago — Rochester
2h 35m stop
1:42 pm — 3:05 pm AA4096 American Airlines
Rochester — Boston
5h 35m
including layover
Find flight
from$435
8:50 am — 2:21 pm
8:50 am — 11:54 am AA1652 American Airlines
Chicago — Philadelphia
1h 6m stop
1:00 pm — 2:21 pm AA788 American Airlines
Philadelphia — Boston
4h 31m
including layover
Find flight
from$349
8:57 am — 3:44 pm
8:57 am — 11:59 am AA593 American Airlines
Chicago — Charlotte
1h 30m stop
1:29 pm — 3:44 pm AA471 American Airlines
Charlotte — Boston
5h 47m
including layover
Find flight
from$260
9:00 am — 5:15 pm
9:00 am — 11:33 am AA2412 American Airlines
Chicago — Dallas
1h 2m stop
12:35 pm — 5:15 pm AA1476 American Airlines
Dallas — Boston
7h 15m
including layover
Find flight
from$445
9:06 am — 2:54 pm
9:06 am — 12:00 pm AA1002 American Airlines
Chicago — Washington D.C.
1h 30m stop
1:30 pm — 2:54 pm AA2119 American Airlines
Washington D.C. — Boston
4h 48m
including layover
Find flight
from$252
9:10 am — 3:02 pm
9:10 am — 12:03 pm AA1002 American Airlines
Chicago — Washington D.C.
1h 27m stop
1:30 pm — 3:02 pm AA2119 American Airlines
Washington D.C. — Boston
4h 52m
including layover
Find flight
from$261
9:10 am — 5:10 pm
9:10 am — 12:03 pm AA1002 American Airlines
Chicago — Washington D.C.
3h 27m stop
3:30 pm — 5:10 pm AA2124 American Airlines
Washington D.C. — Boston
7h
including layover
Find flight
from$414
9:13 am — 4:00 pm
9:13 am — 12:05 pm AA1002 American Airlines
Chicago — Washington D.C.
2h 25m stop
2:30 pm — 4:00 pm AA2149 American Airlines
Washington D.C. — Boston
5h 47m
including layover
Find flight
from$261
9:13 am — 5:10 pm
9:13 am — 12:05 pm AA1002 American Airlines
Chicago — Washington D.C.
3h 25m stop
3:30 pm — 5:10 pm AA2133 American Airlines
Washington D.C. — Boston
6h 57m
including layover
Find flight
from$349
9:30 am — 3:14 pm
9:30 am — 12:38 pm AA349 American Airlines
Chicago — New York
1h 22m stop
2:00 pm — 3:14 pm AA2146 American Airlines
New York — Boston
4h 44m
including layover
Find flight
from$253
9:30 am — 4:11 pm
9:30 am — 12:38 pm AA349 American Airlines
Chicago — New York
2h 22m stop
3:00 pm — 4:11 pm AA2172 American Airlines
New York — Boston
5h 41m
including layover
Find flight
from$253
9:30 am — 5:16 pm
9:30 am — 12:38 pm AA349 American Airlines
Chicago — New York
3h 22m stop
4:00 pm — 5:16 pm AA2128 American Airlines
New York — Boston
6h 46m
including layover
Find flight
from$253
9:30 am — 6:14 pm
9:30 am — 12:40 pm AA349 American Airlines
Chicago — New York
4h 20m stop
5:00 pm — 6:14 pm AA2141 American Airlines
New York — Boston
7h 44m
including layover
Find flight
from$259
9:30 am — 3:29 pm
9:30 am — 12:21 pm AA3668 American Airlines
Chicago — Albany
2h 5m stop
2:26 pm — 3:29 pm 9K1814 Cape Air
Albany — Boston
4h 59m
including layover
Find flight
from$482
10:35 am — 6:16 pm
10:35 am — 1:33 pm AA1668 American Airlines
Chicago — Charlotte
47m stop
2:20 pm — 4:12 pm AA2068 American Airlines
Charlotte — New York
48m stop
5:00 pm — 6:16 pm AA2141 American Airlines
New York — Boston
6h 41m
including layover
Find flight
from$314
1:30 pm — 10:29 pm
1:30 pm — 4:29 pm AA1486 American Airlines
Chicago — Washington D.C.
1h 54m stop
6:23 pm — 8:00 pm AA2654 American Airlines
Washington D.C. — New York
1h 10m stop
9:10 pm — 10:29 pm AA1278 American Airlines
New York — Boston
7h 59m
including layover
Find flight
from$245
5:49 am — 4:47 pm
5:49 am — 8:43 am AA2523 American Airlines
Chicago — Charlotte
1h 18m stop
10:01 am — 12:00 pm AA429 American Airlines
Charlotte — New York
3h 30m stop
3:30 pm — 4:47 pm AA277 American Airlines
New York — Boston
9h 58m
including layover
Find flight
from$234
5:49 am — 1:59 pm
5:49 am — 8:42 am AA2523 American Airlines
Chicago — Charlotte
1h 13m stop
9:55 am — 11:59 am AA429 American Airlines
Charlotte — New York
47m stop
12:46 pm — 1:59 pm AA4052 American Airlines
New York — Boston
7h 10m
including layover
Find flight
from$299
*Departure and arrival times are local. Last updated on 04/25/2019

Flight Information

There are 13 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 10:05 am to 9:30 am. Nonstop flight is 2h 11m. The time difference between Chicago and Boston is 1h.

  • The fastest flight 2h 11m
  • Average flight time 2h 16m
  • The earliest flight 10:05 am
  • The latest flight 9:30 am
  • Distance 852 ml

The cheapest months for traveling to Boston are october, november, december, The most expensive and popular months are april.

The cheapest flight by American Airlines that our users were able to find is $53. This airfare is economy class on one-way AA2384 flight for April 30, 2019 leaving O'Hare International in Chicago at 7:15 am, it includes all taxes and additional fees.

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Other Popular Airlines on the Route

Besides American Airlines there are other 3 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 20 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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