Calgary (YYC) to Chicago (ORD) flights
3 airlines fly nonstop from Calgary (YYC) to Chicago (ORD): American Airlines, United Airlines and WestJet. The two airports are 1,382 miles (2,224 km) apart. American Airlines is in oneworld and United Airlines is in Star Alliance. There are also 21 ways to fly it with one stop, through Minneapolis, Winnipeg and Denver and more.
Airlines flying nonstop from YYC to ORD
- American Airlinesoneworld · bookable with 9 programsWho books it
- United AirlinesStar Alliance · bookable with 13 programsWho books it
- WestJetNot in an alliance · bookable with 3 programsWho books it
Book YYC to ORD with points
Loyalty programs that can book at least one of the nonstop airlines, from the Award Booking Guide.
- Emirates SkywardsBooks United Airlines, WestJet
- Air Canada AeroplanBooks United Airlines
- Air France-KLM Flying BlueBooks WestJet
- Air New Zealand AirpointsBooks United Airlines
- Alaska Atmos RewardsBooks American Airlines
- American AAdvantageBooks American Airlines
- ANA Mileage ClubBooks United Airlines
- Avianca LifeMilesBooks United Airlines
- British Airways ClubBooks American Airlines
- Cathay Pacific Asia MilesBooks American Airlines
- Delta SkyMilesBooks WestJet
- EVA Air Infinity MileageLandsBooks United Airlines
- Finnair PlusBooks American Airlines
- Iberia ClubBooks American Airlines
- JAL Mileage BankBooks American Airlines
- JetBlue TrueBlueBooks United Airlines
- Lufthansa Miles & MoreBooks United Airlines
- Qantas Frequent FlyerBooks American Airlines
- Qatar Airways Privilege ClubBooks American Airlines
- Singapore Airlines KrisFlyerBooks United Airlines
- TAP Miles&GoBooks United Airlines
- Thai Royal Orchid PlusBooks United Airlines
- Turkish Airlines Miles&SmilesBooks United Airlines
- United MileagePlusBooks United Airlines
YYC to ORD with one stop
21 connections, most direct first. 2-stop routings and flight times are in Routes with Pro.
- Via Minneapolis (MSP)Delta Air Lines the whole way
+1 - Via Winnipeg (YWG)Air Canada, WestJet and 1 more, then United Airlines
- Via Denver (DEN)United Airlines the whole way
- Via Detroit (DTW)WestJet, then American Airlines, Delta Air Lines and 1 more
- Via Salt Lake City (SLC)Delta Air Lines the whole way
- Via Nashville (BNA)WestJet, then American Airlines and United Airlines
- Via Toronto (YYZ)Air Canada the whole way+1
- Via Seattle (SEA)Alaska Airlines the whole way
+1 - Via Vancouver (YVR)Air Canada the whole way
- Via Portland (PDX)WestJet, then American Airlines, Alaska Airlines and 1 more
- Via Dallas (DFW)American Airlines the whole way
- Via Ottawa (YOW)Air Canada, WestJet and 1 more, then United Airlines
- Via Atlanta (ATL)WestJet, then American Airlines, Delta Air Lines and 2 more+1
- Via Dulles (IAD)United Airlines the whole way
- Via Las Vegas (LAS)WestJet, then American Airlines, Frontier Airlines and 1 more
YYC to ORD: common questions
Which airlines fly nonstop from YYC to ORD?
American Airlines (oneworld), United Airlines (Star Alliance) and WestJet fly nonstop from Calgary (YYC) to Chicago (ORD).
How far is Calgary from Chicago by plane?
Calgary (YYC) and Chicago (ORD) are 1,382 miles (2,224 km) apart along the great circle, the shortest path a flight can take. Connections add distance on top.
Which points programs can book YYC to ORD award flights?
24 programs can book at least one of the nonstop airlines: Emirates Skywards, Air Canada Aeroplan, Air France-KLM Flying Blue, Air New Zealand Airpoints, Alaska Atmos Rewards, American AAdvantage, ANA Mileage Club, Avianca LifeMiles and 16 more. Which flights each can book depends on its partners, so check the airline before you transfer points.
How many miles does YYC to ORD cost?
It depends on the program: each prices the route from its own chart or dynamically. The Award Flight Pricer compares 30+ programs for YYC to ORD with taxes and fees.
Where can I connect between Calgary and Chicago?
The most direct connections are through Minneapolis (MSP), Winnipeg (YWG), Denver (DEN), Detroit (DTW) and Salt Lake City (SLC). On 11 of them the same airline flies both flights, for example Delta Air Lines through Minneapolis.
More routes
Routes are scheduled nonstop flights. The route data is refreshed monthly; this list was last checked November 11, 2026. Seasonal routes and new launches can be missing or end early, so confirm with the airline before you book. Distances are great-circle, the shortest path between the two airports.