Cheap Flights to Chicago

Flights to Chicago

As one of the top visited cities in the United States, Chicago boasts a vibrant art, culture and entertainment scene, as well as a thriving nightlife. Its praised for its grand and equally innovative architecture which you can see across the city – and most predominantly along the Riverwalk. The third-largest city in America, this bustling metropolis is sure to have something to please every Canadian traveler.

Chicago Travel Guide

Cheap Flights to Chicago

Thinking of taking a vacation to Chicago? From Canada, you can easily book cheap flights to Chicago, flying into either Chicago O'Hare International Airport , or Chicago Midway Airport. Airlines that fly to Chicago O’Hare International Airport from Canada include: Air Canada, American Airlines, and United Airlines. While Porterflights to Chicago arrive at Chicago Midway Airport.

Toronto to Chicago Flights

There are approximately 172 flights from Toronto to Chicago every week. Cheap flights from Toronto to Chicago are available year-round, from both Toronto Pearson International Airport (YYZ) and Billy Bishop Toronto City Airport (YTZ), arriving at either Chicago O'Hare International Airport, or Chicago Midway Airport. Flights to Chicago cost roughly C$ 126 for a one-way fare.

Vancouver to Chicago Flights

Flights from Vancouver to Chicago are popular among both business and leisure travelers. Cheap flights to Chicago from Vancouver are in demand across the whole year. Travelers can expect to pay around C$ 185 for one-way Vancouver to Chicago flights.

Arriving in Chicago

There are two major airports in Chicago, Illinois: Chicago O'Hare International Airport and Chicago Midway Airport.

Arriving at Chicago is O’Hare International Airport

The largest airport in Chicago is O’Hare International Airport in the city’s northwest region and is a major hub for international flights. For those on a budget, the CTA Blue Line station​​​ is located within the airport and offers easy access to downtown Chicago and beyond. A number of airport shuttles and regional buses service O'Hare International Airport (ORD), offering passengers transportation to the city, suburbs and surrounding states.

Arriving at Chicago Midway International Airport

Chicago Midway International Airport is the smaller Chicago’s two airports and is located in southwest Chicago. From Midway International Airport (MDW), you can easily get to the city centre using public transportation. Looking for a more comfortable ride to your accommodation dwellings? A taxi will set you back around US$ 60 to get to downtown Chicago while rideshare cars are slightly cheaper at approximately US $45. Either airport is a great choice for Canadians to fly into when looking for cheap flights to Chicago.

Chicago Travel Information

Traveling to Chicago? Here’s what you need to know to make your journey as smooth as possible.

Essential Chicago Travel Information

Getting Around Chicago Chicago offers the third-largest transportation system in the United States. Tourists will find it relatively easy to navigate the Chicago cityscape with its vast network of public buses and elevated trains, for which fares start at USD $1.
Car Hire, Chicago Enhance your vacation by exploring even more of Chicago. Cheap car rental services are available at both Chicago airports.
Weather in Chicago As Chicago’s nickname suggests, the 'Windy City' can be a frosty adventure in the winter with temperatures as low as 10°C, combined with arctic winds. In summer, the temperature rises to an average of 29°C.
Best Time to Visit Chicago The best time to visit Chicago is in the summer when the beaches and parks come alive with outdoor events. The fall is also a great time to visit as the sun continues to shine, but the city sees fewers tourists and lower hotel prices.

Flights to Chicago: Frequently Asked Questions

When is it best to book flights to Chicago?

Historical data shows that November is the cheapest month to book flights to Chicago from Canada. Flights during this period are 5% cheaper on average than in other months. However, prices will vary depending on departure airport and other factors (such as the day or time that you book, and how far in advance you are searching for flight tickets) can influence flight prices too.

How to find cheap flights to Chicago?

Our data also shows that April is also the cheapest month to fly to Chicago from Canada. Chicago flights bought for travel in April are on average 5% cheaper than flights bought in other months. Make sure you’re getting the best Chicago flights by signing up to Skyscanner Price Alerts.

What time zone is Chicago on?

Chicago is on Central Time, so you’ll need to adjust your watch accordingly.

What to do in Chicago?

Travelers from Canada and the rest of the globe flock to Chicago for its arts, culture and music scenes. Among the most popular things to do in Chicago is to tour the city’s many museums and galleries, including the renowned Art Institute of Chicago, and the Shedd Aquarium. Chicago is frequently named one of the best US cities for sports, so be sure to check out the iconic baseball stadium, Wrigley Field.

What to see in Chicago?

A must-do while you’re in Chicago is to take photo with the mirrored Cloud Gate sculpture in Millennium Park. More impressive Chicago attractions await to be seen from the soaring heights of the 110 storey-tall Willis Tower. However, if you’d rather marvel at the city’s edifices and skyscrapers from the ground, the 90-minute Architecture River Tour will inform you of everything you need to know about the city’s illustrious past and present.

Where to eat in Chicago?

Whether you’re a fan of fine dining, deep-fried grub or a href=""craft beer, Chicago is a great destination to take your tastebuds on an adventure. The Girl and Goat is one of the most-talked about restaurants in the city, receiving rave reviews for both its innovative menu and interior design. Another popular pick is the The Purple Pig which is known for its swine and wine-themed menu. However, you can’t leave Chicago without taking a cheesy bite of the city’s famous deep-dish pizza.

Where to shop in Chicago?

On the hunt to pick up some fashion-forward buys? Head straight to Chicago’s main shopping strip The Magnificent Mile where you can browse everything from luxury goods to high-street fashion.

Where to stay in Chicago?

Chicago has of great places to stay, with 3* hotels on offer from US$ 69/night. Top-rated hotels include the Double Tree by Hilton Chicago Magnificent Mile, and Claridge House. 5* hotels include The Peninsula Chicago and Waldorf Astoria Chicago which can be found from US$ 312/night.

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.

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Airports near Chicago

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.