Cheap Flights from Calgary to Chicago
Cheap Flights from Calgary to Chicago
Looking for cheap flights from Calgary to Chicago? PointsYeah scans award availability across major airline and bank transfer programs in one place, so travelers can compare the lowest points and cash routes faster. Instead of searching each airline separately, users can see pricing from programs like Chase, Amex, Capital One, Citi, and Bilt side by side.
Award prices from Calgary to Chicago vary by season, cabin, and date, but available award flights can start around 13,500 points one way, with premium cabins available at higher mileage levels. The live search above allows filtering by cabin, airline, stops, or maximum points to find the best award flights from Calgary to Chicago for specific travel dates.
2026-11-21
YYC - ORD
Economy | 1 Stop | 5 left
From 13,500 Pts + $66.2
2026-12-02
YYC - ORD
Economy | 1 Stop | 9+ left
From 13,500 Pts + $66.2
2026-12-05
YYC - ORD
Economy | 1 Stop | 9+ left
From 13,500 Pts + $66.2
2026-12-08
YYC - ORD
Economy | 1 Stop | 9+ left
From 13,500 Pts + $66.3
2026-12-09
YYC - ORD
Economy | 1 Stop | 9+ left
From 13,500 Pts + $66.3
2026-12-12
YYC - ORD
Economy | 1 Stop | 9+ left
From 13,500 Pts + $66.3
Calgary to Chicago flight facts
Distance
1,383 mi
2,226 km in a straight line
Estimated flight time
about 3h 15m
In the air, for the straight-line distance
Time difference
Same time zone
Chicago is in the same time zone as Calgary.
Airports in Calgary
YYC · Calgary Intl
Airports in Chicago
DPA · Dupage
MDW · Chicago Midway Intl
ORD · Chicago O'Hare Intl
Premium cabin flights from Calgary to Chicago
Premium cabin
2026-11-10
YYC - ORD
First | 1 Stop | 4 left
From 35,000 Pts + $86.2
Premium cabin
2026-11-14
YYC - ORD
First | 1 Stop | 2 left
From 35,000 Pts + $86.2
Premium cabin
2026-11-17
YYC - ORD
First | 1 Stop | 3 left
From 35,000 Pts + $86.2
Premium cabin
2026-11-10
YYC - ORD
First | 2 Stops | 4 left
From 46,000 Pts + $66.3
Premium cabin
2026-11-12
YYC - ORD
First | 1 Stop | 1 left
From 46,000 Pts + $66.3
Premium cabin
2026-11-13
YYC - ORD
First | 1 Stop | 3 left
From 46,000 Pts + $66.3
Selected hotels for your next stay
Chicago (United States)
Chicago Athletic Association
From 15,000 Pts or $236
Chicago (USA)
ACME Hotel Chicago, Outset Collection by Hilton
From 28,000 Pts or $75
Chicago, IL (USA)
Waldorf Astoria Chicago
From 95,000 Pts or $407
Frequently Asked Questions
The cheapest route from Calgary to Chicago depends on award space, transfer bonuses, and travel dates. PointsYeah compares bank and airline programs in one place so you can find the best points and cash combinations faster.
Yes. Transferable points from Chase, Amex, Capital One, Citi, and Bilt can often be moved to airline partners for flights from Calgary to Chicago.
Yes. Searching metro codes when available helps compare nearby airport combinations for flights from Calgary to Chicago.
Calgary and Chicago are about 1,383 miles (2,226 km) apart in a straight line.
Flying the 1,383-mile straight-line distance takes about 3h 15m in the air, estimated from typical cruising speed. Actual travel time depends on the routing; itineraries with connections take longer.
Chicago is in the same time zone as Calgary.
Departures from Calgary: Calgary Intl (YYC). Arrivals in Chicago: Dupage (DPA), Chicago Midway Intl (MDW), Chicago O'Hare Intl (ORD).
Travelers searching this route also look at other popular routes into Chicago, plus the return trip when we track it. Fares and award space change daily.
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points travel planning experience. Yeah!
