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.
Toronto to Chicago flight schedules
| Flight | Departure Date | Arrival Date | Price | Duration | Number of stops | Updated |
|---|---|---|---|---|---|---|
| Toronto (YTO) - Chicago (CHI) | 2026-11-26 | 2026-11-30 | 286 USD | 3 hours 40 minutes | Direct | 2026-11-04T18:22:25 |
| Toronto (YTO) - Chicago (CHI) | 2026-11-24 | 2026-11-30 | 305 USD | 3 hours 42 minutes | Direct | 2026-11-03T02:33:26 |
| Toronto (YTO) - Chicago (CHI) | 2026-11-22 | 2026-11-30 | 365 USD | 10 hours 48 minutes | Connection | 2026-11-03T09:24:20 |
| Toronto (YTO) - Chicago (CHI) | 2026-12-17 | 2026-12-20 | 369 USD | 3 hours 49 minutes | Direct | 2026-11-03T01:26:23 |
| Toronto (YTO) - Chicago (CHI) | 2026-12-26 | 2027-01-05 | 382 USD | 8 hours 29 minutes | Connection | 2026-11-03T09:28:50 |
| Toronto (YTO) - Chicago (CHI) | 2026-11-22 | 2026-12-26 | 405 USD | 3 hours 45 minutes | Direct | 2026-11-03T09:25:22 |
| Toronto (YTO) - Chicago (CHI) | 2026-11-20 | 2026-11-22 | 425 USD | 3 hours 40 minutes | Direct | 2026-11-02T21:20:05 |
| Toronto (YTO) - Chicago (CHI) | 2026-12-25 | 2027-01-04 | 427 USD | 3 hours 40 minutes | Direct | 2026-11-03T09:27:37 |
| Toronto (YTO) - Chicago (CHI) | 2026-12-26 | 2027-01-04 | 435 USD | 8 hours 29 minutes | Connection | 2026-11-03T12:09:07 |
| Toronto (YTO) - Chicago (CHI) | 2026-11-13 | 2026-11-16 | 454 USD | 3 hours 45 minutes | Direct | 2026-11-04T14:08:23 |
| Toronto (YTO) - Chicago (CHI) | 2026-11-06 | 2026-11-25 | 469 USD | 3 hours 40 minutes | Direct | 2026-10-31T17:02:56 |
| Toronto (YTO) - Chicago (CHI) | 2026-11-13 | 2026-11-15 | 477 USD | 3 hours 40 minutes | Direct | 2026-11-01T14:11:23 |
| Toronto (YTO) - Chicago (CHI) | 2026-11-14 | 2026-11-16 | 483 USD | 35 hours 12 minutes | Connection | 2026-11-03T14:28:54 |
Toronto to Chicago flight status
| Flight | Origin | Destination | Departure | Arrival | Equip |
|---|---|---|---|---|---|
| IB4464 | Toronto (YYZ) | Chicago (ORD) | 12:16 p.m. | 2:06 p.m. | 738 |
| MS9327 | Toronto (YYZ) | Chicago (ORD) | 11 a.m. | noon | None |
| NZ9809 | Toronto (YYZ) | Chicago (ORD) | 7 a.m. | 8 a.m. | |
| 5D2710 | Toronto (YYZ) | Chicago (ORD) | 8:34 a.m. | 2:15 p.m. | E190 |
| UA4608 | Toronto (YYZ) | Chicago (ORD) | 2:33 p.m. | 4:17 p.m. | CR5 |
| UA5512 | Toronto (YYZ) | Chicago (ORD) | 5:38 p.m. | 8:54 p.m. | EMBRAER EMB 175 (short wing) |
| AC509 | Toronto (YYZ) | Chicago (ORD) | 2 p.m. | 2:55 p.m. | Airbus 320-211 |
| UA490 | Toronto (YYZ) | Chicago (ORD) | 9:25 a.m. | 12:29 p.m. | Boeing 737-800 |
| NH7383 | Toronto (YYZ) | Chicago (ORD) | 8:45 a.m. | 9:45 a.m. | ERJ |
| NH7763 | Toronto (YYZ) | Chicago (ORD) | 2:45 p.m. | 3:50 p.m. | 738 |
| UA4603 | Toronto (YYZ) | Chicago (ORD) | 5:45 p.m. | 7 p.m. | CRJ7 |
| AC7611 | Toronto (YYZ) | Chicago (ORD) | 1:40 a.m. | 4:50 a.m. | E75 |
| MQ3430 | Toronto (YYZ) | Chicago (ORD) | 1:01 p.m. | 3:25 p.m. | E75L |
| UA8091 | Toronto (YYZ) | Chicago (ORD) | 9 a.m. | 11 a.m. | E75 |
| UA4551 | Toronto (YYZ) | Chicago (ORD) | 6:55 a.m. | 9:43 a.m. | CRJ7 |
| UA8303 | Toronto (YYZ) | Chicago (ORD) | 9:15 p.m. | 10:30 p.m. | E75 |
| NZ9808 | Toronto (YYZ) | Chicago (ORD) | 11 a.m. | noon | |
| AC503 | Toronto (YYZ) | Chicago (ORD) | 8:05 a.m. | 9 a.m. | Airbus 320-211 |
| UA8307 | Toronto (YYZ) | Chicago (ORD) | 2 p.m. | 2:55 p.m. | EMBRAER EMB 175 |
| NZ9813 | Toronto (YYZ) | Chicago (ORD) | 8:45 a.m. | 9:45 a.m. | |
| QF3305 | Toronto (YYZ) | Chicago (ORD) | 1:17 p.m. | 2:22 p.m. | CR7 |
| UA3984 | Toronto (YYZ) | Chicago (ORD) | 7 a.m. | 8:46 a.m. | ERJ |
| AA3430 | Toronto (YYZ) | Chicago (ORD) | 10:15 a.m. | 12:46 p.m. | E75 |
| JL7451 | Toronto (YYZ) | Chicago (ORD) | 7:20 a.m. | 8:30 a.m. | 738 |
| UA8293 | Toronto (YYZ) | Chicago (ORD) | 6:55 p.m. | 7:52 p.m. | EMBRAER EMB 175 |
| UA2085 | Toronto (YYZ) | Chicago (ORD) | 7:40 p.m. | 11:19 p.m. | Boeing 737-800 |
| AA4408 | Toronto (YYZ) | Chicago (ORD) | 11:49 a.m. | 2 p.m. | EMBRAER EMB 175 |
| UA1423 | Toronto (YYZ) | Chicago (ORD) | 10:02 a.m. | 4 p.m. | Airbus A319 |
| UA424 | Toronto (YYZ) | Chicago (ORD) | 9:09 p.m. | 11:59 p.m. | Boeing 737-700 |
| AC8293 | Toronto (YYZ) | Chicago (ORD) | 12:55 p.m. | 2:41 p.m. | CRJ |
| AC3666 | Toronto (YYZ) | Chicago (ORD) | 1:28 p.m. | 7:10 p.m. | ERJ |
| UA4540 | Toronto (YYZ) | Chicago (ORD) | 6 a.m. | 6:59 a.m. | CR5 |
| AC5137 | Toronto (YYZ) | Chicago (ORD) | 2:45 p.m. | 3:50 p.m. | EMBRAER EMB 175 (short wing) |
| AC7673 | Toronto (YYZ) | Chicago (ORD) | 11:05 a.m. | 12:44 p.m. | E75 |
| AC4990 | Toronto (YYZ) | Chicago (ORD) | 5:27 p.m. | 6:30 p.m. | Airbus A319 |
| AC8533 | Toronto (YYZ) | Chicago (ORD) | 10 a.m. | 11:41 a.m. | |
| BA1870 | Toronto (YYZ) | Chicago (ORD) | 12:25 p.m. | 2:36 p.m. | 737-800 |
| UA3626 | Toronto (YYZ) | Chicago (ORD) | 8 a.m. | 9:33 a.m. | E7W |
| C54954 | Toronto (YYZ) | Chicago (ORD) | 7:50 p.m. | 9:03 p.m. | E45X |
| AC4408 | Toronto (YYZ) | Chicago (ORD) | 11 a.m. | noon | EMBRAER EMB 175 (short wing) |
| AC5141 | Toronto (YYZ) | Chicago (ORD) | 7 a.m. | 8 a.m. | |
| NZ9812 | Toronto (YYZ) | Chicago (ORD) | 9 p.m. | 10:05 p.m. | A319 |
| UA8257 | Toronto (YYZ) | Chicago (ORD) | 6:40 p.m. | 6:53 p.m. | EMBRAER EMB 175 |
| BA2454 | Toronto (YYZ) | Chicago (ORD) | 5:55 p.m. | 6:27 p.m. | E145 |
| UA5141 | Toronto (YYZ) | Chicago (ORD) | 3:26 p.m. | 4:07 p.m. | Boeing 737-700 |
| UA3578 | Toronto (YYZ) | Chicago (ORD) | 6:18 p.m. | 8 p.m. | EMBRAER EMB 175 (short wing) |
| UA8533 | Toronto (YYZ) | Chicago (ORD) | 8:05 a.m. | 9 a.m. | E75 |
| AA3736 | Toronto (YYZ) | Chicago (ORD) | 6:15 a.m. | 9:50 a.m. | E75 |
| AC507 | Toronto (YYZ) | Chicago (ORD) | 12:25 p.m. | 1:22 p.m. | Airbus 320-211 |
| MQ3736 | Toronto (YYZ) | Chicago (ORD) | 6:15 a.m. | 9:50 a.m. | E75L |
| UA8361 | Toronto (YYZ) | Chicago (ORD) | 11:40 a.m. | 4:07 p.m. | E75 |
| NZ9807 | Toronto (YYZ) | Chicago (ORD) | 1 p.m. | 2:06 p.m. | |
| UA4530 | Toronto (YYZ) | Chicago (ORD) | 1:30 p.m. | 3:41 p.m. | CR5 |
| AC511 | Toronto (YYZ) | Chicago (ORD) | 6:50 p.m. | 7:47 p.m. | Airbus 320-211 |
| OO4464 | Toronto (YYZ) | Chicago (ORD) | 6:14 p.m. | 7:37 p.m. | |
| NZ9811 | Toronto (YYZ) | Chicago (ORD) | 2:45 p.m. | 3:50 p.m. | ERJ |
| UA3640 | Toronto (YYZ) | Chicago (ORD) | 7:58 p.m. | 10:32 p.m. | EMBRAER EMB 170 / EMB 175 |
| IB937 | Toronto (YYZ) | Chicago (ORD) | 4:05 p.m. | 7 p.m. | |
| UA5515 | Toronto (YYZ) | Chicago (ORD) | 12:52 p.m. | 4:15 p.m. | EMBRAER EMB 175 (short wing) |
| UA9327 | Toronto (YYZ) | Chicago (ORD) | 6:05 a.m. | 7:05 a.m. | Boeing 737 Max 8 |
| QF3303 | Toronto (YYZ) | Chicago (ORD) | 8:35 p.m. | 11:29 p.m. | CR7 |
| UA8561 | Toronto (YYZ) | Chicago (ORD) | 8:55 p.m. | 10:41 p.m. | E75 |
| UA8694 | Toronto (YYZ) | Chicago (ORD) | 12:25 p.m. | 1:25 p.m. | EMBRAER EMB 175 |
| UA2142 | Toronto (YYZ) | Chicago (ORD) | 2:12 p.m. | 3:57 p.m. | Boeing 737 Max 9 |
| UA8685 | Toronto (YYZ) | Chicago (ORD) | 10:25 a.m. | 11:50 a.m. | EMBRAER EMB 175 |
| WS5579 | Toronto (YYZ) | Chicago (ORD) | 5:37 p.m. | 7:05 p.m. | CR7 |
| NZ9810 | Toronto (YYZ) | Chicago (ORD) | 5:45 p.m. | 6:51 p.m. | 319 |
| AC4961 | Toronto (YYZ) | Chicago (ORD) | 9 p.m. | 10:05 p.m. | EMBRAER EMB 175 (short wing) |
| UA4628 | Toronto (YYZ) | Chicago (ORD) | 3:51 p.m. | 5:39 p.m. | EMBRAER EMB 175 (short wing) |
| NH7807 | Toronto (YYZ) | Chicago (ORD) | 1 p.m. | 2:06 p.m. | E7W |
| QF3270 | Toronto (YYZ) | Chicago (ORD) | 2:29 p.m. | 3:47 p.m. | CR7 |
| AY4106 | Toronto (YYZ) | Chicago (ORD) | 6:26 p.m. | 7:54 p.m. | CR7 |
| SK7701 | Toronto (YYZ) | Chicago (ORD) | 6:15 a.m. | 10:15 a.m. | E75S |
| UA3632 | Toronto (YYZ) | Chicago (ORD) | 9:32 a.m. | 11:15 a.m. | E75L |
| OO3185 | Toronto (YYZ) | Chicago (ORD) | 10:30 a.m. | 12:51 p.m. | CRJ7 |
| UA5491 | Toronto (YYZ) | Chicago (ORD) | 9:15 a.m. | 11:27 a.m. | EMBRAER EMB 175 (short wing) |
| UA5143 | Toronto (YYZ) | Chicago (ORD) | 10:30 a.m. | 11:30 a.m. | Boeing 737 Max 8 |
| QF4907 | Toronto (YYZ) | Chicago (ORD) | 5:58 p.m. | 7:05 p.m. | E75 |
| AC735 | Toronto (YYZ) | Chicago (ORD) | 5:40 p.m. | 7:12 p.m. | A319 |
| AS4017 | Toronto (YYZ) | Chicago (ORD) | 9:10 p.m. | 10:53 p.m. | E75 |
| RJ7520 | Toronto (YYZ) | Chicago (ORD) | 8:29 p.m. | 10 p.m. | CR7 |
| UA5748 | Toronto (YYZ) | Chicago (ORD) | 5:41 p.m. | 7:05 p.m. | CRJ |
| MQ4122 | Toronto (YYZ) | Chicago (ORD) | 12:33 p.m. | 2:57 p.m. | E75L |
| UA5832 | Toronto (YYZ) | Chicago (ORD) | 1:40 p.m. | 4:28 p.m. | EMBRAER EMB 175 (short wing) |
| AC505 | Toronto (YYZ) | Chicago (ORD) | 12:05 p.m. | 1:05 p.m. | Airbus 320-211 |
| 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 |
| UA8281 | Toronto (YYZ) | Chicago (ORD) | 4:30 p.m. | 10:15 a.m. | E75 |
| 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 |
| 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 |
| VS4014 | Toronto (YYZ) | Chicago (ORD) | 10 a.m. | 1:55 p.m. | B752 |
| 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 |
| 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 |
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