Book Cheap Flights from Calgary to Chicago starting from C$139

Chicago, a city defined by its innovative architecture, deep-rooted history, and expansive green spaces along Lake Michigan, offers a compelling experience for any traveller. From its foundational role in jazz and blues music to its world-class museums and parks, the city presents a dynamic blend of urban sophistication and natural beauty. Whether exploring its diverse neighbourhoods, enjoying its culinary scene, or admiring its architectural wonders, Chicago provides a memorable journey into American culture and ingenuity.

Planning a trip from Calgary to Chicago is straightforward. A direct flight typically takes around three hours, offering a quick journey across the border. For those looking to avoid peak travel seasons, the ideal times to fly are generally spring (April to May) or fall (September to October). During these months, the weather is pleasant, perfect for exploring the city's outdoor attractions without the larger crowds or extreme temperatures of summer or winter. Flights are also often more readily available and can be found at more competitive prices.

Begin your journey from Calgary, a major hub for travel to destinations like Chicago and beyond. Calgary is served by one primary airport facilitating commercial flights and passenger discovery.

Calgary International Airport (YYC)

Calgary International Airport is the main air travel facility for the city, connecting travellers to domestic and international flights. This airport features two terminals, offering a range of services from car rental facilities to various dining options, assisting with smooth transitions for passengers embarking on their flight. It is located approximately 17 kilometres northeast of downtown Calgary, making it a convenient starting point for your destination.

Your journey from Calgary to Chicago brings you to one of several airports serving the metropolitan area. Your flight will conclude its discovery in a city known for its extensive air travel infrastructure.

Chicago O'Hare International Airport (ORD)

Chicago O'Hare International Airport is a significant global hub, located approximately 25 kilometres northwest of the city centre. It manages a high volume of both domestic and international air traffic, offering extensive connectivity to destinations worldwide. Travellers arriving here have various ground transportation options, including the CTA Blue Line, Metra trains, and car rental services, to reach their final destination within the city or surrounding regions.

Chicago Midway International Airport (MDW)

Chicago Midway International Airport sits closer to downtown, about 15 kilometres southwest of the city centre. This airport primarily handles domestic flights, serving as a key operational base for several low-cost carriers. It provides direct access to the CTA Orange Line, facilitating a quick commute into the heart of Chicago. Car rental counters and rideshare options are also readily available for onward travel.

Planning your next adventure doesn't have to be a puzzle. We make it simple to compare prices from many airlines, ensuring you always see the best value. Look for flexible fares, which give you extra peace of mind if plans shift. Plus, eDreams Prime members unlock exclusive discounts on flights and hotels. We equip you with the tools to effortlessly shape your ideal journey, making every detail click into place for a smooth and rewarding experience.