American Airlines Toronto to Chicago Flights

Cheapflightsplus.com will find cheap American Airlines flights from Toronto to Chicago. Compare airline ticket prices and book air tickets starting from $118 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 Toronto (ON) — Chicago (IL) 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 june: one-way - $118, two-way – $202.
Direct flights
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Check prices for return flight
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
11:45 am — 12:37 pm
11:45 am — 12:37 pm AA3236 American Airlines
Toronto — Chicago
1h 52m
Find flight
from$149
3:12 pm — 4:08 pm
3:12 pm — 4:08 pm AA3080 American Airlines
Toronto — Chicago
1h 56m
Find flight
from$172
6:30 pm — 7:31 pm
6:30 pm — 7:31 pm AA3526 American Airlines
Toronto — Chicago
2h 1m
Find flight
from$133
7:57 pm — 8:54 pm
7:57 pm — 8:54 pm AA3033 American Airlines
Toronto — Chicago
1h 57m
Find flight
from$125
8:15 am — 9:13 am
8:15 am — 9:13 am AA2352 American Airlines
Toronto — Chicago
1h 58m
Find flight
from$132
8:15 am — 9:14 am
8:15 am — 9:14 am AA2580 American Airlines
Toronto — Chicago
1h 59m
Find flight
from$148
8:16 am — 9:11 am
8:16 am — 9:11 am AA2352 American Airlines
Toronto — Chicago
1h 55m
Find flight
from$133
10:25 am — 2:20 pm
10:25 am — 11:59 am AA4864 American Airlines
Toronto — Philadelphia
56m stop
12:55 pm — 2:20 pm AA2840 American Airlines
Philadelphia — Chicago
4h 55m
including layover
Find flight
from$189
10:25 am — 3:15 pm
10:25 am — 11:59 am AA4864 American Airlines
Toronto — Philadelphia
2h 11m stop
2:10 pm — 3:15 pm WN5522 Southwest Airlines
Philadelphia — Chicago
5h 50m
including layover
Find flight
from$382
10:59 am — 9:35 pm
10:59 am — 12:45 pm AA5517 American Airlines
Toronto — Washington D.C.
7h 36m stop
8:21 pm — 9:35 pm AA2679 American Airlines
Washington D.C. — Chicago
11h 36m
including layover
Find flight
from$123
10:59 am — 7:39 am
+1 day
10:59 am — 12:45 pm AA5517 American Airlines
Toronto — Washington D.C.
17h 45m stop
6:30 am — 7:39 am AA466 American Airlines
Washington D.C. — Chicago
21h 40m
including layover
Find flight
from$124
10:59 am — 7:24 pm
10:59 am — 12:45 pm AA5517 American Airlines
Toronto — Washington D.C.
5h 16m stop
6:01 pm — 7:24 pm AA1486 American Airlines
Washington D.C. — Chicago
9h 25m
including layover
Find flight
from$125
10:59 am — 10:11 pm
10:59 am — 12:45 pm AA5517 American Airlines
Toronto — Washington D.C.
8h 18m stop
9:03 pm — 10:11 pm AA2499 American Airlines
Washington D.C. — Chicago
12h 12m
including layover
Find flight
from$125
10:59 am — 8:41 pm
10:59 am — 12:45 pm AA5517 American Airlines
Toronto — Washington D.C.
6h 30m stop
7:15 pm — 8:41 pm AA363 American Airlines
Washington D.C. — Chicago
10h 42m
including layover
Find flight
from$125
10:59 am — 4:05 pm
10:59 am — 12:45 pm AA5517 American Airlines
Toronto — Washington D.C.
2h 20m stop
3:05 pm — 4:05 pm WN3337 Southwest Airlines
Washington D.C. — Chicago
6h 6m
including layover
Find flight
from$408
10:59 am — 3:50 pm
10:59 am — 12:45 pm AA5517 American Airlines
Toronto — Washington D.C.
2h 5m stop
2:50 pm — 3:50 pm WN5549 Southwest Airlines
Washington D.C. — Chicago
5h 51m
including layover
Find flight
from$634
11:00 am — 8:46 pm
11:00 am — 12:46 pm AA5517 American Airlines
Toronto — Washington D.C.
6h 43m stop
7:29 pm — 8:46 pm AA1015 American Airlines
Washington D.C. — Chicago
10h 46m
including layover
Find flight
from$125
11:04 am — 7:27 am
+1 day
11:04 am — 12:40 pm AA4864 American Airlines
Toronto — Philadelphia
17h 25m stop
6:05 am — 7:27 am AA2164 American Airlines
Philadelphia — Chicago
21h 23m
including layover
Find flight
from$169
11:04 am — 7:30 pm
11:04 am — 12:40 pm AA4864 American Airlines
Toronto — Philadelphia
5h 10m stop
5:50 pm — 7:30 pm AA490 American Airlines
Philadelphia — Chicago
9h 26m
including layover
Find flight
from$242
11:43 am — 5:11 pm
11:43 am — 2:04 pm AA3470 American Airlines
Toronto — Dallas
42m stop
2:46 pm — 5:11 pm AA2223 American Airlines
Dallas — Chicago
6h 28m
including layover
Find flight
from$381
11:50 am — 7:08 pm
11:50 am — 2:10 pm AA3470 American Airlines
Toronto — Dallas
2h 25m stop
4:35 pm — 7:08 pm AA2418 American Airlines
Dallas — Chicago
8h 18m
including layover
Find flight
from$379
11:50 am — 9:13 pm
11:50 am — 2:10 pm AA3470 American Airlines
Toronto — Dallas
4h 30m stop
6:40 pm — 9:13 pm AA2520 American Airlines
Dallas — Chicago
10h 23m
including layover
Find flight
from$379
11:50 am — 7:29 pm
11:50 am — 2:10 pm AA3470 American Airlines
Toronto — Dallas
2h 50m stop
5:00 pm — 7:29 pm AA1463 American Airlines
Dallas — Chicago
8h 39m
including layover
Find flight
from$379
12:14 pm — 5:39 pm
12:14 pm — 2:18 pm AA5137 American Airlines
Toronto — Charlotte
2h 1m stop
4:19 pm — 5:39 pm AA1017 American Airlines
Charlotte — Chicago
6h 25m
including layover
Find flight
from$162
12:14 pm — 6:20 am
+1 day
12:14 pm — 2:19 pm AA5137 American Airlines
Toronto — Charlotte
14h 56m stop
5:15 am — 6:20 am AA226 American Airlines
Charlotte — Chicago
19h 6m
including layover
Find flight
from$162
12:14 pm — 11:47 pm
12:14 pm — 2:19 pm AA5137 American Airlines
Toronto — Charlotte
8h 23m stop
10:42 pm — 11:47 pm AA483 American Airlines
Charlotte — Chicago
12h 33m
including layover
Find flight
from$162
12:14 pm — 7:33 pm
12:14 pm — 2:16 pm AA5137 American Airlines
Toronto — Charlotte
3h 54m stop
6:10 pm — 7:33 pm AA2488 American Airlines
Charlotte — Chicago
8h 19m
including layover
Find flight
from$189
12:14 pm — 11:15 pm
12:14 pm — 2:18 pm AA5137 American Airlines
Toronto — Charlotte
7h 51m stop
10:09 pm — 11:15 pm AA816 American Airlines
Charlotte — Chicago
12h 1m
including layover
Find flight
from$189
12:15 pm — 6:18 am
+1 day
12:15 pm — 2:16 pm AA5698 American Airlines
Toronto — Charlotte
14h 59m stop
5:15 am — 6:18 am AA2938 American Airlines
Charlotte — Chicago
19h 3m
including layover
Find flight
from$189
12:15 pm — 5:18 pm
12:15 pm — 2:16 pm AA5698 American Airlines
Toronto — Charlotte
2h 4m stop
4:20 pm — 5:18 pm AA1017 American Airlines
Charlotte — Chicago
6h 3m
including layover
Find flight
from$242
12:15 pm — 6:58 pm
12:15 pm — 2:16 pm AA5698 American Airlines
Toronto — Charlotte
3h 44m stop
6:00 pm — 6:58 pm AA2488 American Airlines
Charlotte — Chicago
7h 43m
including layover
Find flight
from$284
12:45 pm — 7:22 pm
12:45 pm — 4:05 pm AA2676 American Airlines
Toronto — Miami
40m stop
4:45 pm — 7:22 pm AA1159 American Airlines
Miami — Chicago
7h 37m
including layover
Find flight
from$212
12:59 pm — 8:52 pm
12:59 pm — 4:20 pm AA2676 American Airlines
Toronto — Miami
2h 10m stop
6:30 pm — 8:52 pm AA2303 American Airlines
Miami — Chicago
8h 53m
including layover
Find flight
from$277
1:27 pm — 11:30 pm
1:27 pm — 3:08 pm AA3386 American Airlines
Toronto — New York
6h 52m stop
10:00 pm — 11:30 pm AA2461 American Airlines
New York — Chicago
11h 3m
including layover
Find flight
from$123
1:27 pm — 10:04 pm
1:27 pm — 3:08 pm AA3386 American Airlines
Toronto — New York
5h 22m stop
8:30 pm — 10:04 pm AA196 American Airlines
New York — Chicago
9h 37m
including layover
Find flight
from$123
1:27 pm — 6:23 pm
1:27 pm — 3:08 pm AA3386 American Airlines
Toronto — New York
1h 31m stop
4:39 pm — 6:23 pm AA358 American Airlines
New York — Chicago
5h 56m
including layover
Find flight
from$139
1:27 pm — 7:15 pm
1:27 pm — 3:08 pm AA3386 American Airlines
Toronto — New York
2h 22m stop
5:30 pm — 7:15 pm AA357 American Airlines
New York — Chicago
6h 48m
including layover
Find flight
from$167
1:27 pm — 9:11 pm
1:27 pm — 3:08 pm AA3386 American Airlines
Toronto — New York
4h 22m stop
7:30 pm — 9:11 pm AA336 American Airlines
New York — Chicago
8h 44m
including layover
Find flight
from$167
1:27 pm — 8:14 pm
1:27 pm — 3:08 pm AA3386 American Airlines
Toronto — New York
3h 22m stop
6:30 pm — 8:14 pm AA380 American Airlines
New York — Chicago
7h 47m
including layover
Find flight
from$167
1:29 pm — 10:06 pm
1:29 pm — 3:06 pm AA3386 American Airlines
Toronto — New York
5h 24m stop
8:30 pm — 10:06 pm AA30 American Airlines
New York — Chicago
9h 37m
including layover
Find flight
from$140
1:29 pm — 6:22 pm
1:29 pm — 3:06 pm AA3386 American Airlines
Toronto — New York
1h 24m stop
4:30 pm — 6:22 pm AA381 American Airlines
New York — Chicago
5h 53m
including layover
Find flight
from$167
1:30 pm — 7:53 am
+1 day
1:30 pm — 3:09 pm AA3386 American Airlines
Toronto — New York
15h 21m stop
6:30 am — 7:53 am AA349 American Airlines
New York — Chicago
19h 23m
including layover
Find flight
from$125
2:26 pm — 7:30 pm
2:26 pm — 4:19 pm AA3957 American Airlines
Toronto — New York
1h 1m stop
5:20 pm — 7:30 pm AA1414 American Airlines
New York — Chicago
6h 4m
including layover
Find flight
from$242
2:27 pm — 7:38 am
+1 day
2:27 pm — 4:20 pm AA3957 American Airlines
Toronto — New York
13h 39m stop
5:59 am — 7:38 am AA1279 American Airlines
New York — Chicago
18h 11m
including layover
Find flight
from$125
2:33 pm — 10:06 pm
2:33 pm — 4:15 pm AA3350 American Airlines
Toronto — New York
4h 15m stop
8:30 pm — 10:06 pm AA30 American Airlines
New York — Chicago
8h 33m
including layover
Find flight
from$119
2:33 pm — 8:30 pm
2:33 pm — 4:15 pm AA3350 American Airlines
Toronto — New York
2h 35m stop
6:50 pm — 8:30 pm WN3821 Southwest Airlines
New York — Chicago
6h 57m
including layover
Find flight
from$374
2:44 pm — 10:04 pm
2:44 pm — 4:30 pm AA3350 American Airlines
Toronto — New York
4h stop
8:30 pm — 10:04 pm AA196 American Airlines
New York — Chicago
8h 20m
including layover
Find flight
from$123
2:44 pm — 11:30 pm
2:44 pm — 4:30 pm AA3350 American Airlines
Toronto — New York
5h 30m stop
10:00 pm — 11:30 pm AA2461 American Airlines
New York — Chicago
9h 46m
including layover
Find flight
from$123
2:44 pm — 8:01 am
+1 day
2:44 pm — 4:30 pm AA3350 American Airlines
Toronto — New York
14h stop
6:30 am — 8:01 am AA349 American Airlines
New York — Chicago
18h 17m
including layover
Find flight
from$124
2:44 pm — 8:14 pm
2:44 pm — 4:30 pm AA3350 American Airlines
Toronto — New York
2h stop
6:30 pm — 8:14 pm AA380 American Airlines
New York — Chicago
6h 30m
including layover
Find flight
from$140
2:44 pm — 7:15 pm
2:44 pm — 4:30 pm AA3350 American Airlines
Toronto — New York
1h stop
5:30 pm — 7:15 pm AA357 American Airlines
New York — Chicago
5h 31m
including layover
Find flight
from$162
2:44 pm — 8:05 pm
2:44 pm — 4:30 pm AA3350 American Airlines
Toronto — New York
2h 10m stop
6:40 pm — 8:05 pm WN1111 Southwest Airlines
New York — Chicago
6h 21m
including layover
Find flight
from$308
2:59 pm — 10:53 pm
2:59 pm — 4:40 pm AA3350 American Airlines
Toronto — New York
4h 50m stop
9:30 pm — 10:53 pm AA2461 American Airlines
New York — Chicago
8h 54m
including layover
Find flight
from$125
3:01 pm — 8:15 pm
3:01 pm — 4:40 pm AA3350 American Airlines
Toronto — New York
2h 10m stop
6:50 pm — 8:15 pm WN616 Southwest Airlines
New York — Chicago
6h 14m
including layover
Find flight
from$568
3:02 pm — 11:23 pm
3:02 pm — 4:43 pm AA3350 American Airlines
Toronto — New York
5h 17m stop
10:00 pm — 11:23 pm AA222 American Airlines
New York — Chicago
9h 21m
including layover
Find flight
from$119
3:19 pm — 7:26 pm
3:19 pm — 5:04 pm AA4901 American Airlines
Toronto — Philadelphia
44m stop
5:48 pm — 7:26 pm AA490 American Airlines
Philadelphia — Chicago
5h 7m
including layover
Find flight
from$242
3:19 pm — 9:15 pm
3:19 pm — 5:04 pm AA4901 American Airlines
Toronto — Philadelphia
2h 31m stop
7:35 pm — 9:15 pm WN3898 Southwest Airlines
Philadelphia — Chicago
6h 56m
including layover
Find flight
from$453
3:40 pm — 11:08 pm
3:40 pm — 5:20 pm AA4664 American Airlines
Toronto — New York
4h 10m stop
9:30 pm — 11:08 pm AA2461 American Airlines
New York — Chicago
8h 28m
including layover
Find flight
from$155
3:40 pm — 10:17 pm
3:40 pm — 5:20 pm AA4664 American Airlines
Toronto — New York
3h 10m stop
8:30 pm — 10:17 pm AA196 American Airlines
New York — Chicago
7h 37m
including layover
Find flight
from$155
3:55 pm — 11:45 pm
3:55 pm — 6:09 pm AA1876 American Airlines
Toronto — Charlotte
4h 33m stop
10:42 pm — 11:45 pm AA483 American Airlines
Charlotte — Chicago
8h 50m
including layover
Find flight
from$118
3:55 pm — 8:33 am
+1 day
3:55 pm — 6:09 pm AA2943 American Airlines
Toronto — Charlotte
13h 26m stop
7:35 am — 8:33 am AA1668 American Airlines
Charlotte — Chicago
17h 38m
including layover
Find flight
from$125
3:55 pm — 6:18 am
+1 day
3:55 pm — 6:09 pm AA2943 American Airlines
Toronto — Charlotte
11h 6m stop
5:15 am — 6:18 am AA2938 American Airlines
Charlotte — Chicago
15h 23m
including layover
Find flight
from$125
3:55 pm — 11:28 pm
3:55 pm — 6:09 pm AA2943 American Airlines
Toronto — Charlotte
4h 21m stop
10:30 pm — 11:28 pm AA483 American Airlines
Charlotte — Chicago
8h 33m
including layover
Find flight
from$125
3:55 pm — 8:57 pm
3:55 pm — 6:09 pm AA2943 American Airlines
Toronto — Charlotte
1h 50m stop
7:59 pm — 8:57 pm AA583 American Airlines
Charlotte — Chicago
6h 2m
including layover
Find flight
from$125
3:55 pm — 9:30 pm
3:55 pm — 6:09 pm AA1876 American Airlines
Toronto — Charlotte
2h 6m stop
8:15 pm — 9:30 pm AA583 American Airlines
Charlotte — Chicago
6h 35m
including layover
Find flight
from$162
3:58 pm — 11:47 pm
3:58 pm — 6:13 pm AA1876 American Airlines
Toronto — Charlotte
4h 29m stop
10:42 pm — 11:47 pm AA483 American Airlines
Charlotte — Chicago
8h 49m
including layover
Find flight
from$119
3:58 pm — 10:45 am
+1 day
3:58 pm — 6:13 pm AA1876 American Airlines
Toronto — Charlotte
15h 17m stop
9:30 am — 10:45 am AA1136 American Airlines
Charlotte — Chicago
19h 47m
including layover
Find flight
from$119
3:59 pm — 11:15 pm
3:59 pm — 6:12 pm AA1876 American Airlines
Toronto — Charlotte
3h 57m stop
10:09 pm — 11:15 pm AA816 American Airlines
Charlotte — Chicago
8h 16m
including layover
Find flight
from$125
5:14 pm — 11:40 pm
5:14 pm — 7:08 pm AA3586 American Airlines
Toronto — New York
2h 22m stop
9:30 pm — 11:40 pm AA314 American Airlines
New York — Chicago
7h 26m
including layover
Find flight
from$357
5:20 pm — 10:11 pm
5:20 pm — 7:09 pm AA5542 American Airlines
Toronto — Washington D.C.
1h 54m stop
9:03 pm — 10:11 pm AA2499 American Airlines
Washington D.C. — Chicago
5h 51m
including layover
Find flight
from$140
5:20 pm — 7:39 am
+1 day
5:20 pm — 7:09 pm AA5542 American Airlines
Toronto — Washington D.C.
11h 21m stop
6:30 am — 7:39 am AA466 American Airlines
Washington D.C. — Chicago
15h 19m
including layover
Find flight
from$167
5:22 pm — 10:12 pm
5:22 pm — 7:20 pm AA5542 American Airlines
Toronto — Washington D.C.
1h 43m stop
9:03 pm — 10:12 pm AA2679 American Airlines
Washington D.C. — Chicago
5h 50m
including layover
Find flight
from$123
5:55 pm — 10:50 pm
5:55 pm — 7:41 pm AA4931 American Airlines
Toronto — Philadelphia
1h 44m stop
9:25 pm — 10:50 pm AA1680 American Airlines
Philadelphia — Chicago
5h 55m
including layover
Find flight
from$125
5:55 pm — 7:19 am
+1 day
5:55 pm — 7:41 pm AA4931 American Airlines
Toronto — Philadelphia
10h 19m stop
6:00 am — 7:19 am AA1116 American Airlines
Philadelphia — Chicago
14h 24m
including layover
Find flight
from$189
6:00 am — 11:59 pm
6:00 am — 8:12 am AA5167 American Airlines
Toronto — Charlotte
14h 45m stop
10:57 pm — 11:59 pm AA483 American Airlines
Charlotte — Chicago
18h 59m
including layover
Find flight
from$118
6:00 am — 5:39 pm
6:00 am — 8:12 am AA5167 American Airlines
Toronto — Charlotte
8h 8m stop
4:20 pm — 5:39 pm AA1017 American Airlines
Charlotte — Chicago
12h 39m
including layover
Find flight
from$118
6:00 am — 10:39 am
6:00 am — 8:12 am AA5167 American Airlines
Toronto — Charlotte
1h 13m stop
9:25 am — 10:39 am AA1136 American Airlines
Charlotte — Chicago
5h 39m
including layover
Find flight
from$162
6:00 am — 10:33 am
6:00 am — 8:12 am AA5665 American Airlines
Toronto — Charlotte
1h 23m stop
9:35 am — 10:33 am AA2080 American Airlines
Charlotte — Chicago
5h 33m
including layover
Find flight
from$168
6:10 pm — 6:22 am
+1 day
6:10 pm — 7:50 pm AA4931 American Airlines
Toronto — Philadelphia
9h 10m stop
5:00 am — 6:22 am AA2324 American Airlines
Philadelphia — Chicago
13h 12m
including layover
Find flight
from$125
6:10 pm — 7:27 am
+1 day
6:10 pm — 7:50 pm AA4931 American Airlines
Toronto — Philadelphia
10h 15m stop
6:05 am — 7:27 am AA2164 American Airlines
Philadelphia — Chicago
14h 17m
including layover
Find flight
from$125
6:15 am — 10:31 am
6:15 am — 8:03 am AA5603 American Airlines
Toronto — Washington D.C.
1h 32m stop
9:35 am — 10:31 am AA1167 American Airlines
Washington D.C. — Chicago
5h 16m
including layover
Find flight
from$168
6:29 am — 11:30 pm
6:29 am — 8:14 am AA3955 American Airlines
Toronto — New York
13h 46m stop
10:00 pm — 11:30 pm AA2461 American Airlines
New York — Chicago
18h 1m
including layover
Find flight
from$125
6:29 am — 11:17 am
6:29 am — 8:14 am AA3955 American Airlines
Toronto — New York
1h 16m stop
9:30 am — 11:17 am AA519 American Airlines
New York — Chicago
5h 48m
including layover
Find flight
from$125
6:30 am — 11:23 pm
6:30 am — 8:17 am AA3955 American Airlines
Toronto — New York
13h 43m stop
10:00 pm — 11:23 pm AA222 American Airlines
New York — Chicago
17h 53m
including layover
Find flight
from$119
6:30 am — 2:53 pm
6:30 am — 8:12 am AA3955 American Airlines
Toronto — New York
5h 18m stop
1:30 pm — 2:53 pm AA30 American Airlines
New York — Chicago
9h 23m
including layover
Find flight
from$125
6:30 am — 10:53 pm
6:30 am — 8:12 am AA3955 American Airlines
Toronto — New York
13h 18m stop
9:30 pm — 10:53 pm AA2461 American Airlines
New York — Chicago
17h 23m
including layover
Find flight
from$125
6:30 am — 10:53 am
6:30 am — 8:12 am AA3955 American Airlines
Toronto — New York
1h 18m stop
9:30 am — 10:53 am AA129 American Airlines
New York — Chicago
5h 23m
including layover
Find flight
from$168
6:31 am — 1:20 pm
6:31 am — 8:17 am AA3955 American Airlines
Toronto — New York
3h 13m stop
11:30 am — 1:20 pm AA337 American Airlines
New York — Chicago
7h 49m
including layover
Find flight
from$119
6:31 am — 11:23 pm
6:31 am — 8:17 am AA3955 American Airlines
Toronto — New York
13h 43m stop
10:00 pm — 11:23 pm AA222 American Airlines
New York — Chicago
17h 52m
including layover
Find flight
from$119
6:31 am — 3:13 pm
6:31 am — 8:17 am AA3955 American Airlines
Toronto — New York
5h 13m stop
1:30 pm — 3:13 pm AA349 American Airlines
New York — Chicago
9h 42m
including layover
Find flight
from$119
6:32 am — 11:20 am
6:32 am — 8:14 am AA3955 American Airlines
Toronto — New York
1h 16m stop
9:30 am — 11:20 am AA1924 American Airlines
New York — Chicago
5h 48m
including layover
Find flight
from$119
6:35 pm — 0:39 am
+1 day
6:35 pm — 8:58 pm AA1111 American Airlines
Toronto — Dallas
1h 23m stop
10:21 pm — 0:39 am AA2585 American Airlines
Dallas — Chicago
7h 4m
including layover
Find flight
from$355
6:35 pm — 7:45 am
+1 day
6:35 pm — 8:58 pm AA1111 American Airlines
Toronto — Dallas
8h 24m stop
5:22 am — 7:45 am AA2812 American Airlines
Dallas — Chicago
14h 10m
including layover
Find flight
from$379
6:35 pm — 9:33 am
+1 day
6:35 pm — 8:58 pm AA1111 American Airlines
Toronto — Dallas
10h 4m stop
7:02 am — 9:33 am AA2180 American Airlines
Dallas — Chicago
15h 58m
including layover
Find flight
from$434
6:35 pm — 7:44 am
+1 day
6:35 pm — 8:57 pm AA1111 American Airlines
Toronto — Dallas
8h 23m stop
5:20 am — 7:44 am AA2513 American Airlines
Dallas — Chicago
14h 9m
including layover
Find flight
from$434
7:00 am — 12:29 pm
7:00 am — 8:38 am AA4992 American Airlines
Toronto — Philadelphia
2h 18m stop
10:56 am — 12:29 pm AA1920 American Airlines
Philadelphia — Chicago
6h 29m
including layover
Find flight
from$119
7:00 am — 1:48 pm
7:00 am — 8:38 am AA4992 American Airlines
Toronto — Philadelphia
3h 47m stop
12:25 pm — 1:48 pm AA2840 American Airlines
Philadelphia — Chicago
7h 48m
including layover
Find flight
from$119
7:00 am — 10:57 am
7:00 am — 8:38 am AA4992 American Airlines
Toronto — Philadelphia
47m stop
9:25 am — 10:57 am AA2095 American Airlines
Philadelphia — Chicago
4h 57m
including layover
Find flight
from$119
7:00 am — 4:57 pm
7:00 am — 8:40 am AA4992 American Airlines
Toronto — Philadelphia
6h 50m stop
3:30 pm — 4:57 pm AA1941 American Airlines
Philadelphia — Chicago
10h 57m
including layover
Find flight
from$123
7:00 am — 11:53 am
7:00 am — 8:40 am AA4992 American Airlines
Toronto — Philadelphia
1h 49m stop
10:29 am — 11:53 am AA518 American Airlines
Philadelphia — Chicago
5h 53m
including layover
Find flight
from$125
7:00 am — 12:15 pm
7:00 am — 8:38 am AA4992 American Airlines
Toronto — Philadelphia
2h 22m stop
11:00 am — 12:15 pm WN1614 Southwest Airlines
Philadelphia — Chicago
6h 15m
including layover
Find flight
from$393
7:00 am — 12:05 pm
7:00 am — 8:38 am AA4992 American Airlines
Toronto — Philadelphia
2h 12m stop
10:50 am — 12:05 pm WN1863 Southwest Airlines
Philadelphia — Chicago
6h 5m
including layover
Find flight
from$414
7:00 am — 12:00 pm
7:00 am — 8:38 am AA4992 American Airlines
Toronto — Philadelphia
2h 12m stop
10:50 am — 12:00 pm WN3973 Southwest Airlines
Philadelphia — Chicago
6h
including layover
Find flight
from$440
7:05 am — 2:25 pm
7:05 am — 8:48 am AA4992 American Airlines
Toronto — Philadelphia
4h 12m stop
1:00 pm — 2:25 pm AA2608 American Airlines
Philadelphia — Chicago
8h 20m
including layover
Find flight
from$125
7:15 am — 12:28 pm
7:15 am — 9:18 am AA5689 American Airlines
Toronto — Charlotte
2h 12m stop
11:30 am — 12:28 pm AA2817 American Airlines
Charlotte — Chicago
6h 13m
including layover
Find flight
from$167
7:15 pm — 11:45 pm
7:15 pm — 9:28 pm AA5139 American Airlines
Toronto — Charlotte
1h 14m stop
10:42 pm — 11:45 pm AA483 American Airlines
Charlotte — Chicago
5h 30m
including layover
Find flight
from$119
7:15 pm — 6:18 am
+1 day
7:15 pm — 9:28 pm AA5139 American Airlines
Toronto — Charlotte
7h 47m stop
5:15 am — 6:18 am AA226 American Airlines
Charlotte — Chicago
12h 3m
including layover
Find flight
from$119
7:15 pm — 11:28 pm
7:15 pm — 9:22 pm AA5705 American Airlines
Toronto — Charlotte
1h 8m stop
10:30 pm — 11:28 pm AA483 American Airlines
Charlotte — Chicago
5h 13m
including layover
Find flight
from$125
7:15 pm — 8:33 am
+1 day
7:15 pm — 9:22 pm AA5705 American Airlines
Toronto — Charlotte
10h 13m stop
7:35 am — 8:33 am AA1668 American Airlines
Charlotte — Chicago
14h 18m
including layover
Find flight
from$125
7:15 pm — 6:45 am
+1 day
7:15 pm — 9:28 pm AA5139 American Airlines
Toronto — Charlotte
8h 32m stop
6:00 am — 6:45 am WN536 Southwest Airlines
Charlotte — Chicago
12h 30m
including layover
Find flight
from$449
7:15 pm — 6:15 am
+1 day
7:15 pm — 9:28 pm AA5139 American Airlines
Toronto — Charlotte
7h 57m stop
5:25 am — 6:15 am WN3927 Southwest Airlines
Charlotte — Chicago
12h
including layover
Find flight
from$593
7:30 am — 11:44 pm
7:30 am — 9:36 am AA5496 American Airlines
Toronto — Charlotte
13h 6m stop
10:42 pm — 11:44 pm AA483 American Airlines
Charlotte — Chicago
17h 14m
including layover
Find flight
from$118
7:30 am — 5:39 pm
7:30 am — 9:36 am AA5496 American Airlines
Toronto — Charlotte
6h 43m stop
4:19 pm — 5:39 pm AA1017 American Airlines
Charlotte — Chicago
11h 9m
including layover
Find flight
from$120
7:30 am — 12:42 pm
7:30 am — 9:36 am AA5496 American Airlines
Toronto — Charlotte
1h 49m stop
11:25 am — 12:42 pm AA2817 American Airlines
Charlotte — Chicago
6h 12m
including layover
Find flight
from$140
8:27 am — 11:13 pm
8:27 am — 10:10 am AA4887 American Airlines
Toronto — Philadelphia
11h 30m stop
9:40 pm — 11:13 pm AA1680 American Airlines
Philadelphia — Chicago
15h 46m
including layover
Find flight
from$120
8:27 am — 5:17 pm
8:27 am — 10:10 am AA4887 American Airlines
Toronto — Philadelphia
5h 30m stop
3:40 pm — 5:17 pm AA1941 American Airlines
Philadelphia — Chicago
9h 50m
including layover
Find flight
from$125
8:27 am — 12:38 pm
8:27 am — 10:10 am AA4887 American Airlines
Toronto — Philadelphia
55m stop
11:05 am — 12:38 pm AA1920 American Airlines
Philadelphia — Chicago
5h 11m
including layover
Find flight
from$125
9:10 am — 9:51 pm
9:10 am — 11:00 am AA5603 American Airlines
Toronto — Washington D.C.
9h 55m stop
8:55 pm — 9:51 pm AA2679 American Airlines
Washington D.C. — Chicago
13h 41m
including layover
Find flight
from$140
9:10 am — 6:26 pm
9:10 am — 11:00 am AA5603 American Airlines
Toronto — Washington D.C.
6h 30m stop
5:30 pm — 6:26 pm AA1486 American Airlines
Washington D.C. — Chicago
10h 16m
including layover
Find flight
from$167
9:10 am — 8:11 pm
9:10 am — 11:00 am AA5603 American Airlines
Toronto — Washington D.C.
8h 15m stop
7:15 pm — 8:11 pm AA4100 American Airlines
Washington D.C. — Chicago
12h 1m
including layover
Find flight
from$253
9:15 am — 1:39 pm
9:15 am — 10:50 am AA4887 American Airlines
Toronto — Philadelphia
1h 30m stop
12:20 pm — 1:39 pm AA2866 American Airlines
Philadelphia — Chicago
5h 24m
including layover
Find flight
from$123
9:15 am — 4:57 pm
9:15 am — 10:50 am AA4887 American Airlines
Toronto — Philadelphia
4h 40m stop
3:30 pm — 4:57 pm AA1941 American Airlines
Philadelphia — Chicago
8h 42m
including layover
Find flight
from$123
9:15 am — 6:10 pm
9:15 am — 10:50 am AA4887 American Airlines
Toronto — Philadelphia
5h 57m stop
4:47 pm — 6:10 pm AA2374 American Airlines
Philadelphia — Chicago
9h 55m
including layover
Find flight
from$125
9:15 am — 1:48 pm
9:15 am — 10:53 am AA4887 American Airlines
Toronto — Philadelphia
1h 32m stop
12:25 pm — 1:48 pm AA2840 American Airlines
Philadelphia — Chicago
5h 33m
including layover
Find flight
from$140
9:15 am — 5:26 pm
9:15 am — 10:53 am AA4887 American Airlines
Toronto — Philadelphia
4h 58m stop
3:51 pm — 5:26 pm AA33 American Airlines
Philadelphia — Chicago
9h 11m
including layover
Find flight
from$162
9:15 am — 7:26 pm
9:15 am — 10:53 am AA4887 American Airlines
Toronto — Philadelphia
6h 55m stop
5:48 pm — 7:26 pm AA490 American Airlines
Philadelphia — Chicago
11h 11m
including layover
Find flight
from$189
9:15 am — 2:10 pm
9:15 am — 10:53 am AA4887 American Airlines
Toronto — Philadelphia
2h 7m stop
1:00 pm — 2:10 pm WN4053 Southwest Airlines
Philadelphia — Chicago
5h 55m
including layover
Find flight
from$512
11:00 am — 6:23 pm
11:00 am — 12:46 pm AA5517 American Airlines
Toronto — Washington D.C.
1h 14m stop
2:00 pm — 3:26 pm AA4319 American Airlines
Washington D.C. — New York
1h 13m stop
4:39 pm — 6:23 pm AA358 American Airlines
New York — Chicago
8h 23m
including layover
Find flight
from$227
1:29 pm — 8:31 pm
1:29 pm — 3:05 pm AA3386 American Airlines
Toronto — New York
1h 55m stop
5:00 pm — 6:30 pm AA4322 American Airlines
New York — Washington D.C.
35m stop
7:05 pm — 8:31 pm AA363 American Airlines
Washington D.C. — Chicago
8h 2m
including layover
Find flight
from$567
5:20 pm — 11:23 pm
5:20 pm — 7:09 pm AA5542 American Airlines
Toronto — Washington D.C.
51m stop
8:00 pm — 9:16 pm AA2123 American Airlines
Washington D.C. — New York
44m stop
10:00 pm — 11:23 pm AA222 American Airlines
New York — Chicago
7h 3m
including layover
Find flight
from$409
5:20 pm — 6:10 am
+1 day
5:20 pm — 7:09 pm AA5542 American Airlines
Toronto — Washington D.C.
2h 51m stop
10:00 pm — 11:04 pm AA1726 American Airlines
Washington D.C. — Pittsburgh
6h 41m stop
5:45 am — 6:10 am WN2204 Southwest Airlines
Pittsburgh — Chicago
13h 50m
including layover
Find flight
from$576
5:22 pm — 11:30 pm
5:22 pm — 7:20 pm AA5542 American Airlines
Toronto — Washington D.C.
40m stop
8:00 pm — 9:18 pm AA2123 American Airlines
Washington D.C. — New York
42m stop
10:00 pm — 11:30 pm AA2461 American Airlines
New York — Chicago
7h 8m
including layover
Find flight
from$196
5:55 pm — 6:55 am
+1 day
5:55 pm — 7:40 pm AA4931 American Airlines
Toronto — Philadelphia
1h 40m stop
9:20 pm — 10:37 pm AA1640 American Airlines
Philadelphia — Nashville
6h 53m stop
5:30 am — 6:55 am WN550 Southwest Airlines
Nashville — Chicago
14h
including layover
Find flight
from$293
7:15 pm — 6:30 am
+1 day
7:15 pm — 9:28 pm AA5139 American Airlines
Toronto — Charlotte
1h 16m stop
10:44 pm — 0:23 am AA2692 American Airlines
Charlotte — Minneapolis
4h 42m stop
5:05 am — 6:30 am WN2362 Southwest Airlines
Minneapolis — Chicago
12h 15m
including layover
Find flight
from$490
7:15 pm — 6:40 am
+1 day
7:15 pm — 9:28 pm AA5139 American Airlines
Toronto — Charlotte
1h 16m stop
10:44 pm — 0:23 am AA2692 American Airlines
Charlotte — Minneapolis
4h 52m stop
5:15 am — 6:40 am WN3703 Southwest Airlines
Minneapolis — Chicago
12h 25m
including layover
Find flight
from$767
*Departure and arrival times are local. Last updated on 06/20/2019

Flight Information

There are 8 flights by American Airlines from Toronto to Chicago every week with departures from Pearson International, Toronto Island, Buttonville Municipal. All flights arrive at Chicago FSS, Midway, O'Hare International, Chicago NAS, Merrill C Meigs (closed), Dupage County, Pal-Waukee.

Departures start from 10:25 am to 9:15 am. Nonstop flight is 1h 52m. The time difference between Toronto and Chicago is 1h.

  • The fastest flight 1h 52m
  • Average flight time 1h 57m
  • The earliest flight 10:25 am
  • The latest flight 9:15 am
  • Distance 436 ml

The cheapest months for traveling to Chicago are august, october, december, The most expensive and popular months are november, june, february.

The cheapest flight by American Airlines that our users were able to find is $118. This airfare is economy class on one-way AA1876 flight for August 31, 2019 leaving Pearson International in Toronto at 3:55 pm, it includes all taxes and additional fees.

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Other Popular Airlines on the Route

Besides American Airlines there are other 5 airline carriers between Toronto and Chicago. Please review schedules and prices from the most popular airlines to find the best airfare deals from Toronto to Chicago.

Nonstop flights

There are 66 direct flights every day from Toronto. Airlines and fares are below:

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Connecting Flights

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

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  • 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.

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