$170 Cheap Flights from Chicago (ORD) to Calgary (YYC)

Chicago (ORD) to Calgary (YYC) at a glance

Discover a range of airlines offering flights from Chicago (ORD) to Calgary (YYC) on this exciting international route. You can compare choices from both full-service and budget carriers to find the best flights from Chicago that suit your travel plans, budget, and schedule. As you plan your visit to explore Calgary's iconic attractions and vibrant neighborhoods, gather all the essential details for your journey from O'Hare International Airport (ORD) to Calgary International Airport (YYC).

• Fastest flight duration: around 3h 45m non-stop
• Route distance: roughly 1,400 miles (2,250 km)
• Flights per week: around 20+ flights with multiple daily departures on average
• Typical fares (one-way): economy tickets often range from $70–$370, depending on seasonality and how far ahead you book

Flights from O'Hare International Airport (ORD) to Calgary International Airport (YYC)

According to recent traveler bookings, the top airlines flying from Chicago to Calgary are favored for their non-stop and one-stop options. Popular layover points include Minneapolis - St. Paul International Airport (MSP) with a layover of about 4 hours and 15 minutes, Pearson International Airport (YYZ) with roughly a 2-hour layover, and Salt Lake City International Airport (SLC) offering a 4-hour and 30-minute layover. These choices provide flexibility in balancing price, total travel time, and cabin class to help you find the ideal itinerary.

• United: This full-service airline provides both non-stop and one-stop flights, with one-way ticket prices generally falling between $75 and $465. It represents about 36% of the departures along this route, with a standard non-stop travel time of 3 hours and 45 minutes.
• American Airlines: As a full-service carrier, American Airlines offers non-stop and one-stop flights, with one-way fares typically ranging from $75 to $375. It accounts for roughly 28% of departures on this route, with a usual non-stop flight duration of 3 hours and 45 minutes.
• WestJet: This low-cost airline specializes in non-stop services, with one-way fares generally between $70 and $260. It makes up about 17% of the departures for this route, with an overall journey time of 3 hours and 45 minutes.
• Delta: Offering both non-stop and one-stop service, Delta is a full-service airline with one-way fares typically between $100 and $275. It contributes approximately 12% of the departures on this route, with a one-stop flight time of 5 hours and 30 minutes, totaling about 8 hours and 30 minutes.
• Air Canada: This full-service carrier provides non-stop and one-stop options, with one-way fares usually ranging from $70 to $485. It represents around 8% of the departures on this route, with a typical one-stop journey taking 5 hours and 30 minutes and a total travel time of approximately 8 hours and 30 minutes.

Travelers flying from Chicago to Calgary have the option to upgrade their experience. American Airlines offers a business class, while United features a first-class service, and Air Canada also provides business class for a comfortable journey.

Best time to fly from Chicago (ORD) to Calgary (YYC)

The most popular months for travelers flying from Chicago to Calgary are June, July, and August, when peak temperatures in Calgary reach up to 62.8°F in July. If you prefer quieter travel, consider November, the least busy and relatively cheaper time to visit with fewer crowds and temperatures around 26.2°F. For better deals, October usually offers the lowest average one-way fare around $139. Flight availability peaks in July, with approximately 37 flights per week, making it easier to find convenient departure times.

• Cheapest time to fly: October usually offers good deals with average one-way fare around $139, roughly 30% cheaper than the yearly average.
• Most flight options: July has the highest number of flights from Chicago to Calgary, with approximately 37 flights per week, giving you more flexibility in scheduling your trip.

*Average one-way fare is based on Expedia flight booking data from January 2025 to April 2026 for the specified route and travel class and may change depending on availability, dates, and demand.

Alternative routes from Chicago (ORD) to Calgary (YYC)

• Chicago to Calgary (MDW-YYC): Midway International Airport (MDW) is located approximately 16 miles from O'Hare International Airport (ORD).
• Aurora to Calgary (AUZ-YYC): Aurora Municipal Airport (AUZ) lies around 32 miles from O'Hare International Airport (ORD).
• Chicago to Red Deer (ORD-YQF): Red Deer Regional Airport (YQF) is situated about 72 miles from Calgary International Airport (YYC).

How to find the best prices for flights from Chicago (ORD) to Calgary (YYC)

Getting some of the best deals on flights from Chicago to Calgary is all about timing and flexibility. Here are some key tips to help you save:

1. Best times to book and fly: cheaper fares are usually available when booking 2 to 8 weeks in advance, although most travelers tend to book at least 2 months ahead. Afternoon departures from 12 PM to 6 PM often provide lower prices, while morning flights from 5 AM to 12 PM are more popular. Additionally, flying on Tuesday generally results in cheaper rates, but Friday remains the most sought-after travel day.
2. Set up price alerts: stay updated on price changes by using Expedia's Price Tracker. Receive alerts when fares drop for your selected route.
3. Bundle and save: bundle your flight and hotel to save on Expedia, or unlock a hotel deal after booking your flight.*
4. Compare flight options: use Expedia's search tool to compare airlines, routes, direct vs. non-direct flights, and flight times. You can also sort by price to find the most affordable options.
5. Stay flexible with dates: being open to different travel days can sometimes help you find better prices on flights and hotels.
6. Think about luggage: nowadays, it's important to check the airline's baggage policies to find the best value. That may be paying for an additional carry-on bag or booking a ticket with checked luggage included. Either way, double-check your allowance before confirming your booking to avoid excess baggage fees at the airport.

*Members only. Savings vary and are not available on all bundles. Select hotels.

Arriving at Calgary International Airport from O'Hare International Airport

Calgary welcomes travelers from Chicago with a range of transport options based on price, convenience, and proximity. Here's how to reach Calgary efficiently:

• Hotel transfer: Transfers offer a convenient way to reach your hotel in Calgary, with private rides that can be arranged in advance.
• Car rental: Renting a car from Calgary International Airport is a great option if you plan to explore and sightsee beyond the city. Browse cheap car rentals at Calgary International Airport on Expedia.
• Taxi/ride-hailing: Taxis and ride-hailing services may be available from designated pickup areas outside the terminal, check locally on arrival.
• Public transportation: From Calgary International Airport, Martindale Station, a metro station, is located about 3.4 miles away by car.

Chicago to Calgary Flights

The cheapest times to fly from Chicago to Calgary

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Calgary are during the month of December. You can find some of the cheapest flights from Chicago to Calgary with Expedia's search tool and vast selection of airlines.

The best time to book a flight from Chicago to Calgary

Sunday is one of the best days to book for cheap flights from Chicago to Calgary: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

How to find cheap round-trip tickets from Chicago to Calgary

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Calgary in 2026. You can also book with separate airlines for your outbound and return journeys, from $170 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Calgary flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Calgary airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

*Terms apply.

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.