$180 Cheap Flights from Calgary (YYC) to Chicago (ORD)

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

Travel from Calgary (YYC) to Chicago (ORD) with a range of airlines offering various options on this international short-haul route. Whether you prefer full-service or budget carriers, you can compare flights to find the best fit for your budget and schedule as you plan to explore Chicago's iconic attractions and vibrant neighborhoods. Discover essential details for your flight from Calgary International Airport to O'Hare International Airport, ensuring a smooth start to your journey.

• Fastest flight duration: around 3h 30m non-stop
• Route distance: roughly 1,400 miles (2,250 km)
• Flights per week: around 15+ flights with multiple daily departures on average
• Typical fares (one-way): economy tickets often range from $100–$390, depending on seasonality and how far ahead you book

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

Based on recent traveler bookings, here are the top airlines favored for routes from Calgary to Chicago, featuring both non-stop and one-stop flights. Popular layover options include Pearson International Airport (YYZ) with a layover of approximately 2 hours and 15 minutes, Minneapolis - St. Paul International Airport (MSP) at around 5 hours, and Denver International Airport (DEN), also about 2 hours and 15 minutes. This variety allows you to combine price, total travel time, and cabin class to create the ideal travel itinerary.

• American Airlines: This full-service airline provides both non-stop and one-stop options, with one-way ticket prices typically ranging from $100 to $400. It makes up about 28% of departures for this route, with a standard non-stop travel duration of 3 hours and 30 minutes.
• United: As a full-service carrier, United offers non-stop and one-stop flights, with one-way fares generally falling between $100 and $535. Representing roughly 24% of departures on this route, the typical non-stop flight time is also 3 hours and 30 minutes.
• WestJet: This low-cost airline specializes in non-stop flights, with one-way fares usually ranging from $100 to $350. WestJet accounts for approximately 17% of departures for this route, featuring a total travel time of 3 hours and 30 minutes.
• Delta: A full-service airline providing non-stop, one-stop, and multi-stop services, Delta offers one-way fares typically priced between $130 and $325. It holds about 15% of the departures, with a standard non-stop flight duration of 3 hours and 30 minutes.
• Air Canada: This full-service carrier features both non-stop and one-stop options, with one-way fares generally ranging from $100 to $460. Air Canada accounts for around 15% of departures, with a typical one-stop journey lasting 5 hours and 45 minutes in the air, totaling approximately 8 hours and 30 minutes of travel time.

Travelers flying from Calgary to Chicago have the option to enhance their journey with upgraded service. Notable airlines include WestJet offering premium economy, while Delta and United both provide first-class experiences for a more luxurious flight.

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

The most popular months for travelers flying from Calgary to Chicago are June, July, and August, when peak temperatures in Chicago reach up to 73.4°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 42.3°F. For better deals, May usually offers the lowest average one-way fare around $143. Flight availability peaks in July, with approximately 30 flights per week, making it easier to find convenient departure times. December has the fewest flights, with approximately 10 flights per week.

• Cheapest time to fly: May usually offers good deals with average one-way fare around $143, roughly 31% cheaper than the yearly average.
• Most flight options: July has the highest number of flights from Calgary to Chicago, with approximately 30 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 route from Calgary (YYC) to Chicago (ORD)

• Calgary to Chicago (YYC-MDW): Midway International Airport (MDW) is located approximately 16 miles from O'Hare International Airport (ORD). One-way economy ticket prices for this route generally fall between $115 and $380, influenced by the time of year and booking period. Flights are primarily offered as one-stop options, with common layover points including Minneapolis - St. Paul International Airport (MSP) and Detroit Metropolitan Wayne County Airport (DTW). Major airlines operating on this route feature Delta and the budget-friendly WestJet.

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

Getting some of the best deals on flights from Calgary to Chicago 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 typically found when booking 2-8 weeks in advance, although most travelers tend to book at least 2 months ahead. Morning departures (5 am-12 pm) usually offer lower prices, while afternoon flights (12 pm-6 pm) are more popular. Additionally, flying on Wednesday generally provides cheaper options, whereas Sunday is the most popular 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 O'Hare International Airport from Calgary International Airport

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

• Hotel transfer: Transfers offer a convenient way to reach your hotel in Chicago, with private rides that can be arranged in advance.
• Car rental: Renting a car from O'Hare International Airport is a great option if you plan to explore and sightsee beyond the city. Browse cheap car rentals at O'Hare 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 O'Hare International Airport, O'Hare Station, a metro station, is just a short 0.1-mile walk away, while Rosemont Station, a train station, is located about 2.2 miles from the airport and is typically reached by car.

Calgary to Chicago Flights

The cheapest times to fly from Calgary to Chicago

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 Calgary to Chicago are during the month of December. You can find some of the cheapest flights from Calgary to Chicago with Expedia's search tool and vast selection of airlines.

The best time to book a flight from Calgary to Chicago

Sunday is one of the best days to book for cheap flights from Calgary to Chicago: 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 Calgary to Chicago

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 Calgary to Chicago in 2026. You can also book with separate airlines for your outbound and return journeys, from $180 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 Calgary to Chicago 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 Calgary to Chicago 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.