Cheap Flights from Toronto to Chicago
Browse current best options from Toronto. Become a member to unlock all deals and get alerts when new deals appear.
Deals from
Toronto
RatePunk searches hundreds of travel sites at once for deals on flights to Chicago
Prices updated 7 days ago
482 airlines compared
80%+ AI score for best value
Fares are subject to change and may not be available for all dates. (Data last updated Oct 26, 2026.)
Today’s best flight deals from Toronto to Chicago
Explore current cheapest deals departing from Toronto to Chicago
2027-02-17 – 2027-03-16
YTO - Chicago
72% AI deal score
CA$739
CA$348
Round trip
2027-02-17 – 2027-02-23
YTO - Chicago
68% AI deal score
CA$837
CA$360
Round trip
2027-02-16 – 2027-03-16
YTO - Chicago
73% AI deal score
CA$747
CA$362
Round trip
2027-03-09 – 2027-03-16
YTO - Chicago
49% AI deal score
CA$446
CA$363
Round trip
2027-02-17 – 2027-03-09
YTO - Chicago
76% AI deal score
CA$738
CA$372
Round trip
2026-11-19 – 2026-11-22
YTO - Chicago
43% AI deal score
CA$295
CA$376
Round trip
2026-11-25 – 2026-11-28
YTO - Chicago
43% AI deal score
CA$285
CA$384
Round trip
2026-11-20 – 2026-11-27
YTO - Chicago
43% AI deal score
CA$272
CA$384
Round trip
2026-12-22 – 2027-01-02
YTO - Chicago
43% AI deal score
CA$270
CA$384
Round trip
2026-12-21 – 2027-01-03
YTO - Chicago
43% AI deal score
CA$270
CA$384
Round trip
