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 1 day ago
459 airlines compared
80%+ AI score for best value
Fares are subject to change and may not be available for all dates. (Data last updated Sep 7, 2026.)
Today’s best flight deals from Calgary to Chicago
Explore current cheapest deals departing from Calgary to Chicago
2026-10-30 – 2026-11-02
YYC - Chicago
68% AI deal score
CA$347
CA$304
Round trip
2026-10-07 – 2026-10-11
YYC - Chicago
75% AI deal score
CA$436
CA$339
Round trip
2026-09-16 – 2026-10-15
YYC - Chicago
48% AI deal score
CA$287
CA$340
Round trip
2026-11-22 – 2026-11-28
YYC - Chicago
67% AI deal score
CA$373
CA$342
Round trip
2026-10-01 – 2026-10-05
YYC - Chicago
75% AI deal score
CA$441
CA$350
Round trip
2026-09-16 – 2026-10-13
YYC - Chicago
66% AI deal score
CA$375
CA$354
Round trip
2026-09-16 – 2026-10-14
YYC - Chicago
66% AI deal score
CA$375
CA$354
Round trip
2026-11-14 – 2026-11-23
YYC - Chicago
75% AI deal score
CA$449
CA$354
Round trip
2026-09-15 – 2026-10-15
YYC - Chicago
67% AI deal score
CA$392
CA$361
Round trip
2026-09-18 – 2026-10-15
YYC - Chicago
50% AI deal score
CA$368
CA$361
Round trip
