Cheap flights from Calgary to Chicago from $0
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Discover deals on Calgary to Chicago flights
Typical range $0–$0•Cheapest found $0
Checking latest prices...Find cheap flights from Calgary to Chicago
Best
1 stop
8 Feb
DEP
05:35
YYC
1×
15:10
ORD
8h 35m
8 Feb
DEPARTURE
05:35 - 15:10
8h 35m
YYC
1 stop
ORD
1 stop
8 Feb
DEP
07:00
YYC
1×
17:44
ORD
9h 44m
8 Feb
DEPARTURE
07:00 - 17:44
9h 44m
YYC
1 stop
ORD
Air Canada flights from Calgary to Chicago
Our best Air Canada deals on Calgary to Chicago tickets
Best
1 stop
8 Feb
DEP
05:35
YYC
1×
15:10
ORD
8h 35m
8 Feb
DEPARTURE
05:35 - 15:10
8h 35m
YYC
1 stop
ORD
1 stop
8 Feb
DEP
05:35
YYC
1×
15:10
ORD
8h 35m
8 Feb
DEPARTURE
05:35 - 15:10
8h 35m
YYC
1 stop
ORD
WestJet flights from Calgary to Chicago
Our best WestJet deals on Calgary to Chicago tickets
Best
1 stop
8 Feb
DEP
00:30
YYC
1×
10:05
ORD
8h 35m
8 Feb
DEPARTURE
00:30 - 10:05
8h 35m
YYC
1 stop
ORD
1 stop
8 Feb
DEP
09:50
YYC
1×
21:35
ORD
10h 45m
8 Feb
DEPARTURE
09:50 - 21:35
10h 45m
YYC
1 stop
ORD
American Airlines flights from Calgary to Chicago
Our best American Airlines deals on Calgary to Chicago tickets
Best
1 stop
8 Feb
DEP
07:00
YYC
1×
17:44
ORD
9h 44m
8 Feb
DEPARTURE
07:00 - 17:44
9h 44m
YYC
1 stop
ORD
1 stop
8 Feb
DEP
07:00
YYC
1×
17:44
ORD
9h 44m
8 Feb
DEPARTURE
07:00 - 17:44
9h 44m
YYC
1 stop
ORD
Porter Airlines flights from Calgary to Chicago
Our best Porter Airlines deals on Calgary to Chicago tickets
Best
1 stop
8 Feb
DEP
07:00
YYC
1×
17:44
ORD
9h 44m
8 Feb
DEPARTURE
07:00 - 17:44
9h 44m
YYC
1 stop
ORD
What's the cheapest day of the week to fly from Calgary to Chicago?
If your flying dates are flexible, you should consider flying to Chicago on a Tue, as we generally find the cheapest rates on that day. On the other hand, Thu is the most expensive day to fly.
What is the cheapest month to fly from Calgary to Chicago?
The cheapest month for flights from Calgary to Chicago is Oct, where tickets cost $214 on average. The most expensive months are Dec.
JanFebMarAprMayJunJulAugSepOctNovDec
$310$262$214
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Everything you should know
Cheapest one-way flight
$221
Typical prices: $221–$521
When to book
6 weeks
in advance to save around 35%
Good to know
💰
Save money
Compare prices across airlines to find the best deal. Prices can vary significantly.
📅
Be flexible
Flying midweek or in off-peak seasons can save you up to 30% on airfare.
⏰
Book early
Booking 6+ weeks in advance typically offers the best prices.
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Frequently asked questions
The cheapest flight from Calgary to Chicago currently costs AUD $221. Prices typically range from $221 to $521. Prices change frequently, so we recommend booking early and being flexible with your travel dates.