Cheap Flights from Calgary to Chicago
Browse current best options from Calgary. Become a member to unlock all deals and get alerts when new deals appear.
Deals from
Calgary
RatePunk searches hundreds of travel sites at once for deals on flights to Chicago
Prices updated 4 days ago
481 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 19, 2026.)
Today’s best flight deals from Calgary to Chicago
Explore current cheapest deals departing from Calgary to Chicago
2026-11-26 – 2026-12-01
YYC - Chicago
50% AI deal score
CA$361
CA$481
Round trip
2026-10-22 – 2026-10-27
YYC - Chicago
84% AI deal score
CA$770
CA$484
Round trip
2026-10-22 – 2026-10-28
YYC - Chicago
82% AI deal score
CA$706
CA$484
Round trip
2026-11-03 – 2026-11-05
YYC - Chicago
75% AI deal score
CA$621
CA$484
Round trip
2026-12-03 – 2026-12-10
YYC - Chicago
68% AI deal score
CA$466
CA$487
Round trip
2026-10-22 – 2026-10-27
YYC - Chicago
68% AI deal score
CA$497
CA$488
Round trip
2026-12-09 – 2026-12-15
YYC - Chicago
66% AI deal score
CA$350
CA$488
Round trip
2026-10-31 – 2026-11-04
YYC - Chicago
66% AI deal score
CA$404
CA$488
Round trip
2026-10-31 – 2026-11-03
YYC - Chicago
66% AI deal score
CA$407
CA$488
Round trip
2026-11-10 – 2026-11-27
YYC - Chicago
65% AI deal score
CA$406
CA$490
Round trip
