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$150 Cheap Flights from Chicago (CHI) to Calgary (YYC)

View $150 flight on Thu, Dec 24, 2026

Popular airlines from Chicago to Calgary, AB (YYC-Calgary Intl.)

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    • Cheap Flights from Chicago to Calgary (CHI-YYC)

    Prices were available within the past 7 days and start at $150 for one-way flights and $324 for roundtrip, for the period specified. Prices and availability are subject to change.

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    One way

    Roundtrip

    Select Alaska Airlines flight, departing Thu, Dec 3 from Chicago to Calgary, returning Mon, Dec 7, priced at $324 Just found

    Thu, Dec 3 - Mon, Dec 7 · ORD · YYC · Roundtrip

    Select Alaska Airlines flight, departing Thu, Dec 3 from Chicago to Calgary, returning Mon, Dec 7, priced at $329 Just found

    Thu, Dec 3 - Mon, Dec 7 · ORD · YYC · Roundtrip

    Select Alaska Airlines flight, departing Wed, Dec 16 from Chicago to Calgary, returning Thu, Jan 7, priced at $333 Just found

    Wed, Dec 16 - Thu, Jan 7 · ORD · YYC · Roundtrip

    Select Alaska Airlines flight, departing Sat, Dec 5 from Chicago to Calgary, returning Tue, Dec 8, priced at $335 Found 1 day ago

    Sat, Dec 5 - Tue, Dec 8 · ORD · YYC · Roundtrip

    Select Alaska Airlines flight, departing Tue, Dec 8 from Chicago to Calgary, returning Sat, Dec 12, priced at $337 Found 3 hours ago

    Tue, Dec 8 - Sat, Dec 12 · ORD · YYC · Roundtrip

    Select American Airlines flight, departing Wed, Jan 13 from Chicago to Calgary, returning Sun, Jan 17, priced at $338 Found 17 hours ago

    Wed, Jan 13 - Sun, Jan 17 · ORD · YYC · Roundtrip

    Select Alaska Airlines flight, departing Thu, Dec 3 from Chicago to Calgary, returning Mon, Dec 7, priced at $339 Just found

    Thu, Dec 3 - Mon, Dec 7 · ORD · YYC · Roundtrip

    Select Delta flight, departing Tue, Dec 8 from Chicago to Calgary, returning Sat, Dec 12, priced at $345 Found 3 hours ago

    Tue, Dec 8 - Sat, Dec 12 · ORD · YYC · Roundtrip

    Select United flight, departing Fri, Jan 8 from Chicago to Calgary, returning Mon, Jan 11, priced at $351 Found 3 hours ago

    Fri, Jan 8 - Mon, Jan 11 · ORD · YYC · Roundtrip

    Select Air Canada flight, departing Sat, Jan 16 from Chicago to Calgary, returning Tue, Jan 19, priced at $359 Found 4 hours ago

    Sat, Jan 16 - Tue, Jan 19 · ORD · YYC · Roundtrip

    Alternative airports near Calgary

    Prices were available within the past 7 days. Prices and availability are subject to change.

    Select flight to Calgary Intl. YYC. Cheapest and Closest option available. Average driving time to city center is 15 minutes. Flights from $596

    15 min

    Find the cheapest month to fly from Chicago (CHI) to Calgary (YYC)

    December is typically the cheapest month to fly

    From $333 - $749 per traveler.

    View flights in December

    Insights are based on prices from searches for economy trips of 10 days or less on our sites in the last 12 months. Insights are informative only and current prices may differ.

    Book with confidence

    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 $150 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.

    Travel information

    Origin airportChicago Midway Airport
    Destination airportCalgary International Airport
    Distance1,396 miles away
    Airlines servingDelta, WestJet
    Popular airlineDelta
    Roundtrip price$324

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    *Available to One Key members.