1. Home
  2. Flights Search
  3. Flights from Toronto to Chicago

Cheap flights from Toronto to Chicago

Find cheap Chicago to Toronto flights with our free search service. Compare all available fares for direct or connection flights from Chicago to Toronto.

Round-trip
  • One-way
  • Round-trip
1 adult
Adults 12 years or over
1
Children 2-11 years
0
Infants 0-23 months
0
Cancel Done
Economy Class
  • Economy Class
  • Business Class
Done
Done

Toronto to Chicago flight schedules

Flight Departure Date Arrival Date Price Duration Number of stops Updated
Toronto (YTO) - Chicago (CHI) 2026-04-27 2026-04-27 414 USD 31 hours 44 minutes Connection 2026-04-14T04:25:43

Toronto to Chicago flight status

Flight Origin Destination Departure Arrival Equip
QF4907 Toronto (YYZ) Chicago (ORD) 4:33 p.m. 5:28 p.m. E75
AA3430 Toronto (YYZ) Chicago (ORD) 2 p.m. 3:36 p.m. E75
UA8293 Toronto (YYZ) Chicago (ORD) 4:50 p.m. 5:50 p.m. EMBRAER EMB 175
UA8561 Toronto (YYZ) Chicago (ORD) 8:05 p.m. 9:51 p.m. E75
NH7763 Toronto (YYZ) Chicago (ORD) 2:45 p.m. 3:48 p.m. 738
AA3736 Toronto (YYZ) Chicago (ORD) 6:45 a.m. 10:15 a.m. E75
UA8307 Toronto (YYZ) Chicago (ORD) 2:15 p.m. 3:15 p.m. EMBRAER EMB 175
AC5141 Toronto (YYZ) Chicago (ORD) 7 a.m. 8:03 a.m.
UA3626 Toronto (YYZ) Chicago (ORD) 1:04 p.m. 2:48 p.m. E7W
C54954 Toronto (YYZ) Chicago (ORD) 7:38 p.m. 8:57 p.m. E45X
AC8293 Toronto (YYZ) Chicago (ORD) 1:25 p.m. 3:13 p.m. CRJ
UA3578 Toronto (YYZ) Chicago (ORD) 9:10 a.m. 11:26 a.m. EMBRAER EMB 175 (short wing)
AA4408 Toronto (YYZ) Chicago (ORD) 5 p.m. 7:04 p.m. EMBRAER EMB 175
UA8361 Toronto (YYZ) Chicago (ORD) 12:55 p.m. 5:17 p.m. E75
UA8694 Toronto (YYZ) Chicago (ORD) 12:05 p.m. 1:05 p.m. EMBRAER EMB 175
BA1870 Toronto (YYZ) Chicago (ORD) 9:39 p.m. 11:33 p.m. 737-800
UA2085 Toronto (YYZ) Chicago (ORD) 3:35 p.m. 7:27 p.m. Boeing 737-800
NH7807 Toronto (YYZ) Chicago (ORD) 1 p.m. 2:01 p.m. E7W
UA1423 Toronto (YYZ) Chicago (ORD) 10:09 a.m. 4:04 p.m. Airbus A319
IB937 Toronto (YYZ) Chicago (ORD) 4:05 p.m. 7 p.m.
JL7451 Toronto (YYZ) Chicago (ORD) 6:15 a.m. 7:25 a.m. 738
AC7673 Toronto (YYZ) Chicago (ORD) 10:15 a.m. 11:54 a.m. E75
AC507 Toronto (YYZ) Chicago (ORD) 2:15 p.m. 3:15 p.m. Airbus 320-211
AC8533 Toronto (YYZ) Chicago (ORD) 10 a.m. 11:39 a.m.
AS4017 Toronto (YYZ) Chicago (ORD) 9:10 p.m. 10:53 p.m. E75
UA8257 Toronto (YYZ) Chicago (ORD) 8:35 a.m. 8:48 a.m. EMBRAER EMB 175
NZ9809 Toronto (YYZ) Chicago (ORD) 7 a.m. 8:03 a.m.
UA8533 Toronto (YYZ) Chicago (ORD) 8:15 a.m. 9:10 a.m. E75
AC4990 Toronto (YYZ) Chicago (ORD) 5:20 p.m. 6:23 p.m. Airbus A319
UA4603 Toronto (YYZ) Chicago (ORD) 12:48 p.m. 2:37 p.m. CRJ7
UA5515 Toronto (YYZ) Chicago (ORD) 12:57 p.m. 4:35 p.m. EMBRAER EMB 175 (short wing)
5D2710 Toronto (YYZ) Chicago (ORD) 8:25 a.m. 1:55 p.m. E190
UA5141 Toronto (YYZ) Chicago (ORD) 6:15 a.m. 6:55 a.m. Boeing 737-700
UA8091 Toronto (YYZ) Chicago (ORD) 9 a.m. 11 a.m. E75
UA490 Toronto (YYZ) Chicago (ORD) 9:15 a.m. 12:24 p.m. Boeing 737-800
UA5832 Toronto (YYZ) Chicago (ORD) 1:35 p.m. 4:23 p.m. EMBRAER EMB 175 (short wing)
UA2142 Toronto (YYZ) Chicago (ORD) 6:50 p.m. 9:47 p.m. Boeing 737 Max 9
UA8303 Toronto (YYZ) Chicago (ORD) 5:55 p.m. 7:16 p.m. E75
NZ9813 Toronto (YYZ) Chicago (ORD) 8:50 a.m. 9:50 a.m.
NZ9812 Toronto (YYZ) Chicago (ORD) 9 p.m. 10:03 p.m. A319
NZ9807 Toronto (YYZ) Chicago (ORD) 1 p.m. 2:01 p.m.
NZ9808 Toronto (YYZ) Chicago (ORD) 10:15 a.m. 11:18 a.m.
NZ9811 Toronto (YYZ) Chicago (ORD) 2:45 p.m. 3:48 p.m. ERJ
NZ9810 Toronto (YYZ) Chicago (ORD) 5:20 p.m. 6:23 p.m. 319
AC5137 Toronto (YYZ) Chicago (ORD) 2:45 p.m. 3:48 p.m. EMBRAER EMB 175 (short wing)
MS9327 Toronto (YYZ) Chicago (ORD) 1 p.m. 2:01 p.m. None
BA2454 Toronto (YYZ) Chicago (ORD) 9:03 p.m. 9:43 p.m. E145
AC4961 Toronto (YYZ) Chicago (ORD) 9 p.m. 10:03 p.m. EMBRAER EMB 175 (short wing)
WS5579 Toronto (YYZ) Chicago (ORD) 3:49 p.m. 6:40 p.m. CR7
UA424 Toronto (YYZ) Chicago (ORD) 1:50 p.m. 8:24 p.m. Boeing 737-700
MQ4122 Toronto (YYZ) Chicago (ORD) 9:32 a.m. 11:35 a.m. E75L
MQ3736 Toronto (YYZ) Chicago (ORD) 5:16 a.m. 8:40 a.m. E75L
UA9327 Toronto (YYZ) Chicago (ORD) 6 a.m. 7 a.m. Boeing 737 Max 8
MQ3430 Toronto (YYZ) Chicago (ORD) 4:20 p.m. 5:14 p.m. E75L
AY4106 Toronto (YYZ) Chicago (ORD) 6:17 p.m. 7:17 p.m. CR7
QF3305 Toronto (YYZ) Chicago (ORD) 1:10 p.m. 2:10 p.m. CR7
UA4608 Toronto (YYZ) Chicago (ORD) 6:30 a.m. 7:59 a.m. CR5
UA3632 Toronto (YYZ) Chicago (ORD) 9:15 a.m. 11:02 a.m. E75L
UA3640 Toronto (YYZ) Chicago (ORD) 5 a.m. 6:12 a.m. EMBRAER EMB 170 / EMB 175
QF3303 Toronto (YYZ) Chicago (ORD) 6:40 p.m. 9:29 p.m. CR7
QF3270 Toronto (YYZ) Chicago (ORD) 2:40 p.m. 4 p.m. CR7
UA4530 Toronto (YYZ) Chicago (ORD) 8:40 a.m. 10:57 a.m. CR5
UA4551 Toronto (YYZ) Chicago (ORD) 10:43 a.m. 11:53 a.m. CRJ7
UA3984 Toronto (YYZ) Chicago (ORD) 6:15 a.m. 8:05 a.m. ERJ
NH7383 Toronto (YYZ) Chicago (ORD) 8:50 a.m. 9:50 a.m. ERJ
UA5748 Toronto (YYZ) Chicago (ORD) 7 a.m. 9:05 a.m. CRJ
AC505 Toronto (YYZ) Chicago (ORD) 12:05 p.m. 1:05 p.m. Airbus 320-211
AC4408 Toronto (YYZ) Chicago (ORD) 11 a.m. 12:03 p.m. EMBRAER EMB 175 (short wing)
AC509 Toronto (YYZ) Chicago (ORD) 4:50 p.m. 5:50 p.m. Airbus 320-211
UA5491 Toronto (YYZ) Chicago (ORD) 4:20 p.m. 6:02 p.m. EMBRAER EMB 175 (short wing)
UA4628 Toronto (YYZ) Chicago (ORD) 8 a.m. 9:24 a.m. EMBRAER EMB 175 (short wing)
UA5512 Toronto (YYZ) Chicago (ORD) 5:31 p.m. 8:48 p.m. EMBRAER EMB 175 (short wing)
AC3666 Toronto (YYZ) Chicago (ORD) 9:05 p.m. 10:17 p.m. ERJ
RJ7520 Toronto (YYZ) Chicago (ORD) 5:05 a.m. 10:36 a.m. CR7
IB4464 Toronto (YYZ) Chicago (ORD) 10:54 a.m. 12:47 p.m. 738
OO4464 Toronto (YYZ) Chicago (ORD) 4:40 p.m. 5:36 p.m.
AC7679 Toronto (YYZ) Chicago (ORD) 4:45 p.m. 7:10 p.m. E75
AC8907 Toronto (YYZ) Chicago (ORD) 2:15 p.m. 3:10 p.m. EMBRAER EMB 175
AC7611 Toronto (YYZ) Chicago (ORD) 2:30 a.m. 6 a.m. E75
UA8281 Toronto (YYZ) Chicago (ORD) 4:30 p.m. 10:15 a.m. E75
UA4540 Toronto (YYZ) Chicago (ORD) 5:27 p.m. 6:31 p.m. CR5
UA5143 Toronto (YYZ) Chicago (ORD) 2 p.m. 3 p.m. Boeing 737 Max 8
AC7683 Toronto (YYZ) Chicago (ORD) 7:05 p.m. 7:31 p.m. E75
UA7383 Toronto (YYZ) Chicago (ORD) 12:35 p.m. 7:30 p.m. 319
AC503 Toronto (YYZ) Chicago (ORD) 8:15 a.m. 9:15 a.m. Airbus 320-211
AC511 Toronto (YYZ) Chicago (ORD) 6:30 p.m. 7:24 p.m. Airbus 320-211
UA8685 Toronto (YYZ) Chicago (ORD) 8:15 a.m. 11:19 a.m. EMBRAER EMB 175
AC5588 Toronto (YYZ) Chicago (ORD) 1 p.m. 2:01 p.m. EMBRAER EMB 175 (short wing)
AC515 Toronto (YYZ) Chicago (ORD) 4:45 p.m. 7:31 p.m. E190
AC8903 Toronto (YYZ) Chicago (ORD) 10 a.m. 10:53 a.m. EMBRAER EMB 175
SK7701 Toronto (YYZ) Chicago (ORD) 8:05 a.m. 12:05 p.m. E75S
VS4014 Toronto (YYZ) Chicago (ORD) 10 a.m. 1:55 p.m. B752
AC735 Toronto (YYZ) Chicago (ORD) 8:20 p.m. 9:49 p.m. A319
OO3186 Toronto (YYZ) Chicago (ORD) 7:15 p.m. 8:08 p.m. CRJ7
RJ7738 Toronto (YYZ) Chicago (ORD) 10:36 p.m. 11:51 p.m. None
OO3185 Toronto (YYZ) Chicago (ORD) 3:03 p.m. 4:37 p.m. CRJ7
AC501 Toronto (YYZ) Chicago (ORD) 8 a.m. 8:57 a.m. E190
LH8184 Toronto (YYZ) Chicago (ORD) 6:35 p.m. 8:45 p.m. MD11
AS8430 Toronto (YYZ) Chicago (ORD) 2:52 p.m. 5:34 p.m. CRJ7
UA4990 Toronto (YYZ) Chicago (ORD) 5:30 p.m. 6:27 p.m. Airbus A320-100/200
OO3296 Toronto (YYZ) Chicago (ORD) 5:40 a.m. 6:36 a.m. CR7
AC8769 Toronto (YYZ) Chicago (ORD) 4 p.m. 4:55 p.m. EMBRAER EMB 175
EI6429 Toronto (YYZ) Chicago (ORD) 11 a.m. 12:04 p.m. 319
EI6432 Toronto (YYZ) Chicago (ORD) 5:30 p.m. 6:34 p.m. 320
EI6431 Toronto (YYZ) Chicago (ORD) 3 p.m. 4:02 p.m. None
EI6430 Toronto (YYZ) Chicago (ORD) 7 a.m. 7:51 a.m. E7W
EI6427 Toronto (YYZ) Chicago (ORD) 9 a.m. 9:54 a.m. 320
AC8489 Toronto (YYZ) Chicago (ORD) 2:35 p.m. 3:03 p.m. DH3
WQ2528 Toronto (YYZ) Chicago (ORD) 10:30 p.m. 11:29 p.m. Boeing 737-8Q8
WQ9891 Toronto (YYZ) Chicago (ORD) 4 p.m. 4:50 p.m. Boeing 737-8Q8
RS7701 Toronto (YYZ) Chicago (ORD) 8:40 a.m. 9:21 a.m. E75S
RS7673 Toronto (YYZ) Chicago (ORD) 2:45 p.m. 3:26 p.m. E75S
RS7679 Toronto (YYZ) Chicago (ORD) 3:50 p.m. 4:31 p.m. E75S
RS7509 Toronto (YYZ) Chicago (ORD) 2 p.m. 3:40 p.m. E75S
RS7681 Toronto (YYZ) Chicago (ORD) 5:10 a.m. 6:31 a.m. E75S
RU9045 Toronto (YYZ) Chicago (ORD) 10 a.m. None B748
KD3600 Toronto (YYZ) Chicago (ORD) 6:25 a.m. None MD11
OO7383 Toronto (YYZ) Chicago (ORD) 11:09 a.m. 12:05 p.m.
AC7527 Toronto (YYZ) Chicago (ORD) 10:55 a.m. 11:45 a.m. E75
RS7683 Toronto (YYZ) Chicago (ORD) 1:05 p.m. 2:26 p.m. E75S
RS7611 Toronto (YYZ) Chicago (ORD) 11:35 p.m. 12:16 a.m. E75S
QK489 Toronto (YYZ) Chicago (ORD) None None CRJ2
RS7706 Toronto (YYZ) Chicago (ORD) 6:35 a.m. 7:25 a.m.
RS7407 Toronto (YYZ) Chicago (ORD) 6:15 p.m. 6:55 p.m. E75
OZ6367 Toronto (YYZ) Chicago (ORD) midnight 10:15 p.m. None
MQ9303 Toronto (YYZ) Chicago (ORD) 7:30 a.m. 8:15 a.m. None
MQ3194 Toronto (YYZ) Chicago (ORD) 11:46 a.m. 12:25 p.m. CR7
WX323 Toronto (YYZ) Chicago (ORD) 4:10 p.m. 4:58 p.m. F50
RS7395 Toronto (YYZ) Chicago (ORD) 7:25 a.m. 8:05 a.m. E75
OZ6469 Toronto (YYZ) Chicago (ORD) midnight 6:38 p.m. None
RS7397 Toronto (YYZ) Chicago (ORD) 10:40 a.m. 11:20 a.m. E75
RS7399 Toronto (YYZ) Chicago (ORD) 12:05 p.m. 12:46 p.m. E75
RS7403 Toronto (YYZ) Chicago (ORD) 2:25 p.m. 3:06 p.m. E75
RS7405 Toronto (YYZ) Chicago (ORD) 4:40 p.m. 5:20 p.m. E75
RS7409 Toronto (YYZ) Chicago (ORD) 8:35 p.m. 9:16 p.m. E75
RS7527 Toronto (YYZ) Chicago (ORD) 6:05 p.m. 6:44 p.m. E75S
AC7397 Toronto (YYZ) Chicago (ORD) 10:45 a.m. 11:25 a.m. E75
YX4228 Toronto (YYZ) Chicago (ORD) 6:10 a.m. 7 a.m. E75
4M4157 Toronto (YYZ) Chicago (ORD) 2:55 p.m. 3:43 p.m.
4C3058 Toronto (YYZ) Chicago (ORD) 6:30 a.m. 7:13 a.m. 320
US3134 Toronto (YYZ) Chicago (ORD) 10:19 a.m. 11:08 a.m. CR7
EV5831 Toronto (YYZ) Chicago (ORD) 6:10 a.m. 6:54 a.m. ERJ
MQ9304 Toronto (YYZ) Chicago (ORD) 8 a.m. 8:45 a.m. None
S53542 Toronto (YYZ) Chicago (ORD) 1:58 p.m. 2:49 p.m. E70
MQ3216 Toronto (YYZ) Chicago (ORD) 6:22 p.m. 7:18 p.m. CR7
MQ3134 Toronto (YYZ) Chicago (ORD) 10:19 a.m. 11:08 a.m. CR7
MQ3076 Toronto (YYZ) Chicago (ORD) 8 p.m. 8:55 p.m. ER4
S53519 Toronto (YYZ) Chicago (ORD) 7:33 p.m. 8:26 p.m. E70

Popular Flights Searchs

  • Domestic Destinations
  • International Destinations