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Type in your origin and destination city and we will give you the best flight route options based on flight time and connection time along with airline and airports delays.

Flight routes from Calgary to Chicago

YYC to ORD flights and routes map YYC to ORD. All flight route options from Calgary International, Canada to Chicago O Hare International, Illinois, USA. These routes are operated by 5 different airlines. You can either fly non-stop or choose from 6 different transit flights. The shortest flight time is 3 hours and 25 minutes.

From
To
Canada YYC Calgary Calgary, AB, Canada
USA ORD Chicago O Hare , IL, USA
YYC
Calgary
CanadaCalgary, AB, Canada
Chicago O Hare
USAChicago, IL, USA
ORD
3 direct routes found »
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10 routes with 1 stop found »
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Non-stop routes:

Duration

American Airlines
Non-stop with American Airlines. 0-1 flights per day.
Begins in Feb 2025

SCHEDULE
3h 25m

Begins in Feb 2025
American Airlines
Non-stop with American Airlines.
3h 25m
0-1 flights per day.
Begins in Feb 2025
SCHEDULE
WestJet
Non-stop with WestJet. 0-1 flights per day.
Begins in Feb 2025

SCHEDULE
3h 26m

Begins in Feb 2025
WestJet
Non-stop with WestJet.
3h 26m
0-1 flights per day.
Begins in Feb 2025
SCHEDULE
United Airlines
Non-stop with United Airlines. 1 flight per day.

SCHEDULE
3h 28m

United Airlines
Non-stop with United Airlines.
3h 28m
1 flight per day.
SCHEDULE
Usually in time
Some delays
Usually delayed
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1 stop routes with the same airline:

Duration

Via Minneapolis MSP
1 stop with Delta Air Lines. 2 flights per day.

SCHEDULE
6h 48m

Via Minneapolis MSP
1 stop with Delta Air Lines.
6h 48m
2 flights per day.
SCHEDULE
Via Denver DEN
1 stop with United Airlines. 2-4 flights per day.

SCHEDULE
7h 30m

Via Denver DEN
1 stop with United Airlines.
7h 30m
2-4 flights per day.
SCHEDULE
Via Salt Lake City SLC
1 stop with Delta Air Lines. 1-2 flights per day.

SCHEDULE
8h 33m

Via Salt Lake City SLC
1 stop with Delta Air Lines.
8h 33m
1-2 flights per day.
SCHEDULE
Via Cleveland CLE
1 stop with United Airlines.
Begins in Mar 2025

SCHEDULE
17h 00m

Begins in Mar 2025
Via Cleveland CLE
1 stop with United Airlines.
17h 00m
Begins in Mar 2025
SCHEDULE
Usually in time
Some delays
Usually delayed
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1 stop routes with codeshare or different airlines:

Duration

Via Winnipeg YWG 1 stop with Air Canada.
Only thursdays
CODESHARE

SCHEDULE
7h 15m

Only thursdays
Via Winnipeg YWG
7h 15m
1 stop with Air Canada.
Only thursdays
CODESHARE
SCHEDULE
Via Detroit DTW 1 stop with Delta Air Lines. 0-1 flights per day.
CODESHARE

SCHEDULE
7h 48m

Via Detroit DTW
7h 48m
1 stop with Delta Air Lines. 0-1 flights per day.
CODESHARE
SCHEDULE
Via Minneapolis MSP With Delta Air Lines & American Airlines

SCHEDULE
7h 56m

Via Minneapolis MSP
7h 56m
With Delta Air Lines & American Airlines
SCHEDULE
Via Denver DEN With Air Canada & American Airlines 1-2 flights per day.
CODESHARE

SCHEDULE
8h 46m

Via Denver DEN
8h 46m
With Air Canada & American Airlines 1-2 flights per day.
CODESHARE
SCHEDULE
Via Salt Lake City SLC With Delta Air Lines & American Airlines

SCHEDULE
8h 51m

Via Salt Lake City SLC
8h 51m
With Delta Air Lines & American Airlines
SCHEDULE
Via Cleveland CLE With United Airlines & American Airlines
Begins in Mar 2025

SCHEDULE
16h 55m

Begins in Mar 2025
Via Cleveland CLE
16h 55m
With United Airlines & American Airlines
Begins in Mar 2025
SCHEDULE
Usually in time
Some delays
Usually delayed
SELECT DATE & CHECK PRICE
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Calgary to Chicago flights

With over 185 flights every week and 9 different airlines you have a wide option of flights to choose from. You can fly non-stop to Chicago (ORD) from Calgary (YYC) with American Airlines, United Airlines or WestJet but if a stopover option suits you better you can choose to fly via Winnipeg, Detroit or any other of the 6 alternatives with flight connections.

Calgary to Chicago with American Airlines

You can fly non-stop every weekday with flights departing at 13 or 15 in the afternoon. American Airlines is a member of the air alliance OneWorld.

With Delta Air Lines

If you choose to fly with Delta Air Lines from Calgary to Chicago you can make a transit either via Minneapolis or via Salt Lake City. The route via Minneapolis is 1 hour and 45 minutes faster. Delta Air Lines is a member of SkyTeam.

Distance & flight times: (YYC) to (ORD)

The shortest flight time between YYC and ORD is 3 hours and 23 minutes.

ViaTotal flight timeLayover timeMiles
Direct3h 23m-1389 (2235 km)
YWG Winnipeg7h 15m2h 40m1454 (2339 km)
DTW Detroit7h 48m52m1808 (2909 km)
MSP Minneapolis7h 56m43m1389 (2235 km)
DEN Denver8h 46m3h 58m1794 (2887 km)
SLC Salt Lake City8h 51m1h 29m1977 (3181 km)
CLE Cleveland16h 55m1h 40m1984 (3192 km)
The flight times and layover times in the table above are approximate and vary depending on flight number, aircraft, airline, weather and time of day.YYC-ORD flight routesCalgary to Chicago flight routes illustrated on a map.
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Calgary - Chicago route map and flight paths
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Unpublished Flight Rates From Calgary to Chicago
From Calgary to USA

Below is a list of other destinations to USA from Calgary International with either direct flights or 1 stop connections.

From Canada to Chicago

Below is a list of other cities in Canada with flights to Chicago with either non-stop or connecting flights.

You can fly to Chicago (ORD) from Calgary (YYC) non-stop with American Airlines, United Airlines or WestJet. The flight takes approximately 3 hours and 23 minutes. If you travel with a connecting flight instead, for example via Winnipeg, the total flight time will be 7 hours and 15 minutes.

If you are interested in direct flights, you can choose from American Airlines, United Airlines or WestJet. If you choose to fly with stops instead you can fly with Air Canada, Delta Air Lines, American Airlines or United Airlines.

The flight time between Calgary, YYC and Chicago O Hare International, ORD, is 3 hours and 23 minutes. The distance is 1794 miles (or 2887 kilometers).

Yes, you can fly non-stop to ORD from YYC with American Airlines, United Airlines or WestJet.

A codeshare agreement means that cooperating airlines are able to sell seats on each other’s flights. This means that you are able to travel to more destinations than your airline of choice normally offers. Codeshare flights are also beneficial because of the seamless transits you can get with connecting flights from the same airline. The downside of choosing a codeshare flight can be that you in some cases can’t upgrade codeshare flights or use elite benefits.

A connecting or transit flight means that you reach your final destination through two or more flights – in other words a non-direct flight. You will change to a new aircraft after your first flight, this may include moving to another terminal at the airport aswell. The time required to transfer passengers and luggage between flights is called Minimum Connecting Time (MCT) and are always taken into account here on Flightroutes.com.

If you bought your whole flight on a single ticket, the airline will book you on the next available connecting flight.

With connecting flights, checked in luggage is most commonly forwarded to your final destination when buying a single ticket for both flights.

If you miss your connecting flight due to circumstances outside your control such as your first flight being delayed, you should turn to your airline who will provide you with a seat on the next available flight. This is usually done free of charge, and only applies if you purchased your trip as one ticket. If the next connecting flight is the following day, the airline usually provides accommodation and meals.
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