Flights from Calgary to Chicago – Airlines & connecting routes
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YYC to MDW – All flight route options from Calgary International, Canada to Chicago Midway International, Illinois, USA. These flights are operated by Delta Air Lines & WestJet through 2 different flight connections. The shortest flight time is 5 hours and 21 minutes. See the full flight schedule and time table, including departure times, airlines and stopover details to find the best option for you.
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Calgary to Chicago flights
With over 30 flights every week and 2 different airlines you have a wide range of options. While flying to Chicago from Calgary you will be doing a stopover in either Minneapolis (MSP) or Detroit (DTW).
Are there any non-stop flights from YYC to MDW?
There are no direct or non-stop flights from Calgary International, YYC to Chicago Midway International, MDW.
Calgary to Chicago with Delta Air Lines
If you fly from Calgary with Delta Air Lines you will do a stopover in Minneapolis, MSP before reaching Chicago. This flight trip will take 5 hours and 21 minutes and you can fly every weekday with departures at 06:35, 06:40 or 06:45. Delta Air Lines is a member of SkyTeam.
Distance & flight times: Calgary International to Midway International Airport
The shortest flight time between YYC and MDW is 5 hours and 21 minutes.
Via | Total flight time | Layover time | Distance |
---|---|---|---|
MSP Minneapolis | 5h 21m | 1h 1m | 1404 miles (2259 km) |
DTW Detroit | 8h 22m | 3h 18m | 1802 miles (2899 km) |

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From Calgary to USA
Below is a list of other destinations to USA from Calgary International with either direct flights or 1 stop connections.
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DFW Dallas Direct
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ORD Chicago Direct
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ATL Atlanta Direct
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DEN Denver Direct
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JFK New York Direct
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MIA Miami
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CLT Charlotte Direct
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LAX Los Angeles Direct
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EWR New York Direct
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IAH Houston Direct
From Canada to Chicago
Below is a list of other cities in Canada with flights to Chicago with either non-stop or connecting flights.