Flight INFO & American Airlines(AA) flights from Calgary to Chicago
| Cheapest one-way flight price | US$96 |
|---|---|
| Cheapest return ticket price | US$231 |
| Cheapest month | October |
| Peak season for travel | January |
| Flight distance | 2,248.84 km |
| Average flight time | 3 hours 36 minutes |
| Popular airline | Air Canada |
Book American Airlines(AA) flights from Calgary to Chicago
- One way
- Round-trip
- direct cheapest
YYC07:003h 35mNonstopORD11:35Calgary - Chicago|Thu, Jun 11|American AirlinesUS$162US$35955% offSearch55% offUS$359US$162 - YYC06:153h 30mNonstopORD10:45Calgary - Chicago|Tue, Jun 9|American AirlinesUS$172US$35952% offSearch52% offUS$359US$172
- YYC13:413h 45mNonstopORD18:26Calgary - Chicago|Mon, Jun 8|American AirlinesUS$194US$35946% offSearch46% offUS$359US$194
- YYC07:003h 35mNonstopORD11:35Calgary - Chicago|Fri, Jun 12|American AirlinesUS$195SearchUS$195
- YYC13:413h 45mNonstopORD18:26Calgary - Chicago|Wed, Jun 10|American AirlinesUS$195SearchUS$195
- YYC13:413h 45mNonstopORD18:26Calgary - Chicago|Thu, Jun 18|American AirlinesUS$203SearchUS$203
- YYC06:303h 25mNonstopORD10:55Calgary - Chicago|Mon, Jun 15|American AirlinesUS$216SearchUS$216
- YYC07:003h 35mNonstopORD11:35Calgary - Chicago|Wed, Jun 24|American AirlinesUS$217SearchUS$217
- YYC06:153h 30mNonstopORD10:45Calgary - Chicago|Mon, Jun 22|American AirlinesUS$230SearchUS$230
- YYC07:003h 35mNonstopORD11:35Calgary - Chicago|Tue, Jun 16|American AirlinesUS$232SearchUS$232
- YYC06:153h 30mNonstopORD10:45Calgary - Chicago|Tue, Jun 23|American AirlinesUS$234SearchUS$234
- YYC07:003h 35mNonstopORD11:35Calgary - Chicago|Wed, Jul 1|American AirlinesUS$246SearchUS$246
- YYC07:003h 35mNonstopORD11:35Calgary - Chicago|Thu, Jun 25|American AirlinesUS$252SearchUS$252
- YYC07:003h 35mNonstopORD11:35Calgary - Chicago|Fri, Jun 19|American AirlinesUS$259SearchUS$259
- YYC07:003h 35mNonstopORD11:35Calgary - Chicago|Wed, Jun 17|American AirlinesUS$262SearchUS$262
- YYC07:003h 35mNonstopORD11:35Calgary - Chicago|Mon, Jun 29|American AirlinesUS$304SearchUS$304
- YYC07:003h 35mNonstopORD11:35Calgary - Chicago|Tue, Jul 7|American AirlinesUS$304SearchUS$304
- YYC13:413h 45mNonstopORD18:26Calgary - Chicago|Fri, Jun 26|American AirlinesUS$306SearchUS$306
- YYC07:003h 35mNonstopORD11:35Calgary - Chicago|Wed, Jul 8|American AirlinesUS$314SearchUS$314
- YYC13:203h 25mNonstopORD17:45Calgary - Chicago|Sun, Jun 14|American AirlinesUS$315SearchUS$315
- YYC07:003h 35mNonstopORD11:35Calgary - Chicago|Sun, Jun 28|American AirlinesUS$327SearchUS$327
- YYC14:143h 45mNonstopORD18:59Calgary - Chicago|Sat, Jun 13|American AirlinesUS$337SearchUS$337
- YYC06:4516h 54m1 stopsORD00:39Calgary - Chicago|Thu, Jun 11|American AirlinesUS$178SearchUS$178
- YYC06:4523h 45m1 stopsORD07:30Calgary - Chicago|Fri, Jun 19|American AirlinesUS$187SearchUS$187
- YYC12:5010h 52m1 stopsORD00:42Calgary - Chicago|Tue, Jun 9|American AirlinesUS$200SearchUS$200
- YYC06:4516h 54m1 stopsORD00:39Calgary - Chicago|Wed, Jun 24|American AirlinesUS$201SearchUS$201
- YYC06:4516h 54m1 stopsORD00:39Calgary - Chicago|Mon, Jun 8|American AirlinesUS$206SearchUS$206
- YYC06:4516h 54m1 stopsORD00:39Calgary - Chicago|Sat, Jun 13|American AirlinesUS$267SearchUS$267
- YYC06:4516h 54m1 stopsORD00:39Calgary - Chicago|Wed, Jul 1|American AirlinesUS$293SearchUS$293
- YYC06:4512h 26m1 stopsORD20:11Calgary - Chicago|Tue, Jun 30|American AirlinesUS$306SearchUS$306
YYC13:0012h 26mNonstopCHI14:00Calgary - Chicago|Mon, Sep 6|Normal AirlineFind more flightsFind more flights
American Airlines(AA) flights from Calgary to Chicago & Flight Schedule
Flight info.
Departure
Arrival
Weekly Schedule
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AA1633
American Airlines
07:00
YYC
11:35
ORD
S M T W T F SSearch -
AA2389
American Airlines
13:41
YYC
18:26
ORD
S M T W T - SSearch -
AA1973
American Airlines
12:50
YYC
17:40
DFW
S M T W T F SSearch -
AA2346
American Airlines
21:05
DFW
23:32
ORD
S M T W T F SSearch -
AA1973
American Airlines
12:50
YYC
17:40
DFW
S M T W T F SSearch -
AA1193
American Airlines
22:14
DFW
00:39
ORD
S M T W T F SSearch -
AA2521
American Airlines
06:45
YYC
11:32
DFW
S M T W T F SSearch -
AA1893
American Airlines
17:35
DFW
20:11
ORD
S M T W T F SSearch -
AA2521
American Airlines
06:45
YYC
11:32
DFW
S M T W T F SSearch -
AA1193
American Airlines
22:14
DFW
00:39
ORD
S M T W T F SSearch -
AA1973
American Airlines
12:50
YYC
17:40
DFW
S M T W T F SSearch -
AA1360
American Airlines
05:02
DFW
07:30
ORD
S M T W T F SSearch -
AA2521
American Airlines
06:45
YYC
11:32
DFW
S M T W T F SSearch -
AA1360
American Airlines
05:02
DFW
07:30
ORD
S M T W T F SSearch
American Airlines(AA) flights from Calgary to Chicago Flight Booking FAQ
-
Which airlines offer direct flights from Calgary to Chicago?
At the moment, you can catch a nonstop flight from Calgary to Chicago with the following airlines, including: WestJet Selected airlines are based on historical data collected from flight bookings users made on Trip.com within the last 90 days. -
How long is a flight from Calgary to Chicago?
It takes about 3 hours 36 minutes to fly from Calgary to Chicago. -
When is the best time to book flights from Calgary to Chicago?
By analyzing data from all airlines on the Trip.com flight calendar, it looks like the best time to book a flight from Calgary to Chicago is around 40 days (6 weeks) in advance, and the best time to fly is usually on Tuesday, Wednesday, and Saturday. Tuesday typically offers the cheapest flights for departure, while Saturday offers the best return deals. -
How many flights are there per week from Calgary to Chicago?
Based on Trip.com data in the past 4 weeks, there is 16 flight per week flying from Calgary to Chicago. You can check the weekly schedule for popular airlines on this route below: WestJet: S/M/T/W/T/F/S -- WS1610 (11:56) -
When are flight tickets from Calgary (YYC) to Chicago (CHI) the cheapest?
The cheapest months to fly from Calgary to Chicago is October, when demand for travel is lower. -
Which upcoming date is cheapest to fly from Calgary to Chicago on?
After crunching the numbers on our June flight calendar, it's currently cheapest to fly from Calgary to Chicago on June 10, 2026 with WestJet, with prices starting at US$232. -
Which airports can I fly to for Chicago from Calgary?
You can land at any one of the following hubs in Chicago, with Calgary International Airport to Chicago O'Hare International Airport (YYC-ORD) is by far the most common option on this route: Chicago Midway International Airport (MDW) Chicago O'Hare International Airport (ORD) Chicago Rockford International Airport (RFD). -
Is there any time difference between Calgary and Chicago?
The time difference between Chicago and Calgary is 1h. -
How do I change or cancel my ticket from Calgary to Chicago?
Tickets can only be changed or canceled if permitted by airline policy. To submit a change or cancellation request, go to the flight bookings page, select the option to change or cancel your booking, choose the relevant passengers and segment, and submit a request. Please note that additional charges may apply according to the airline ticket policy. However, if the flight has been rescheduled and you would like to change or cancel your ticket, you can submit an involuntary cancellation request. For more details about change and cancellation policies, please check the customer support pages.
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