A stunning view of Chicago's skyline and river with prominent skyscrapers and bridges on a cloudy day. — flights from Calgary to Chicago
CalgaryChicago

Flights from Calgary to Chicago

Nonstop flights from Calgary (YYC) to Chicago (ORD) take about 3h 17m (2,224 km). American Airlines and United Airlines fly it. Lowest fare seen: $174 one-way, nonstop (22 Oct 2026).

All flights to Chicago →

Photo of Chicago: Mik Dominguez on Pexels.

When you land in Chicago

The airport transfer and the few things worth sorting before you fly.

A stunning view of Chicago's skyline and river with prominent skyscrapers and bridges on a cloudy day. — arriving in Chicago

Airport transfer

ORD → Chicago, booked before you fly

A private driver meets you in arrivals at a price agreed when you book. Book with Welcome Pickups.

See transfer prices
Before you flyAirport lounges at Calgary →4 lounges at Calgary AirportTrains, buses and taxi faresORD to Chicago: getting into town →Early arrival or late flightLuggage storage in Chicago →11 drop-off points, from $4.90

Things to book in Chicago

All 59 things to do in Chicago →
Skyline view of Chicago's iconic skyscrapers including the John Hancock Center.from €24.10
John Hancock Center 4.5 · 3,029 Tiqets reviews
The historic Tribune Tower in Chicago, featuring its gothic architecture and American flag.from €26.78
Tribune Tower 4.6 · 2,764 Tiqets reviews
View of the historic Wrigley Building in downtown Chicago, showcasing its classic architecture.from €13.38
The Wrigley Building 4.6 · 2,762 Tiqets reviews
Silhouette of visitors walking through a tunnel at Museum Campus, leading outdoors.from €26.78
Museum Campus 4.6 · 2,641 Tiqets reviews

Find hotels in Chicago

Hotels, hostels & more · Trip.com

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Airlines flying Calgary to Chicago

Carriers on YYC–ORD according to our route data and nonstop fares seen as of 22 Oct 2026. Not a complete list.

✈ American Airlinesnonstop fare seen✈ United Airlinesnonstop fare seen

Calgary to Chicago fares by month

Cheapest month seen for a nonstop flight: Oct 2026, from $174 one-way. Lowest one-way fares seen for departures in each month, read 22 Oct 2026.

DepartingNonstop fromCheaper with stops
Oct 2026$17428 Oct 2026 · American Airlines—
Nov 2026$30622 Nov 2026 · United Airlines$192 · 1 stop22 Nov 2026
Dec 2026$26919 Dec 2026 · American Airlines$198 · 1 stop19 Dec 2026 · United Airlines

When to go for the lowest fare

The next few weeks were the cheapest to fly: from $174 in October 2026, against $198 at best later on.

Nonstop or with a stop

A connection undercut nonstop in 2 of 2 months with both fares.

From Travelpayouts flight-search data, city to city (Calgary to Chicago, any airport), USD, read 22 Oct 2026. These are fares that were on sale, not a guarantee of today's price; an airline is named only where we know it flies this route.

More for this trip

Frequently asked questions — Calgary to Chicago flights

How long is the flight from Calgary to Chicago?
A nonstop flight from Calgary (YYC) to Chicago (ORD) takes about 3h 17m, covering 2,224 km. That is an estimate from the distance — actual time varies with the airline, aircraft and winds, and connecting itineraries take longer.
How far is Calgary from Chicago by air?
The great-circle distance between Calgary International Airport and Chicago O'Hare International Airport is 2,224 km (1,382 miles), a medium-haul route.
Which airlines fly from Calgary to Chicago?
Airlines with flights or nonstop fares on the YYC–ORD route include American Airlines and United Airlines. This is not a complete list — schedules change by season, so check the current options before booking.
How much does a flight from Calgary to Chicago cost?
The lowest one-way fare seen recently on YYC–ORD was $174 USD with American Airlines (nonstop), departing 28 Oct 2026, found in fare searches as of 22 Oct 2026. Fares change constantly and depend on the date, so check the current price before booking.
What is the cheapest month to fly from Calgary to Chicago?
In fares seen on 22 Oct 2026, departures in October 2026 were cheapest, from $174 one-way, against $198 for December 2026, the dearest month. Fares change daily, so check your own dates.
Do I need a visa to travel from Calgary to Chicago?
It depends on your passport. Some nationalities can enter Chicago visa-free or get a visa on arrival; others must apply in advance. Use AirConnect's Visa Checker to see the rules for your passport.

Sources: fares from Travelpayouts flight-search data, seen 22 Oct 2026; airlines from each carrier's published network and nonstop fares on sale; distance from OurAirports coordinates; flight time estimated from distance. Fares change daily.

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