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Low-cost flights from Toronto to Chicago

Known as the Windy City, Chicago is located on the shores of Lake Michigan and is the third most populated city in the United States. Catch a game at Wrigley Stadium, walk in the footsteps of infamous mobsters including Al Capone, enjoy a long adored Chicagoan treat; the donut, admire history at the Museum of Natural History, grab a slice of deep-dish pizza and take in the sites of the city. No matter what you love to do you'll find something for everyone in Chicago!

Everyday flight deals from Toronto to Chicago

Book low cost flights to Chicago directly with Swoop, Canada's ultra-low fare airline. We make travel affordable, easy and accessible so you can spend less on the journey and more at your destination.

Chicago's skyline with a highway and waterfront views including the river at sunset.
Toronto to Chicago

One-way fares from

$99

Chicago travel tips

  • How to get around Chicago

    Public transit in Chicago is both easy to use and very affordable. There's a Blue Line train station located in O'Hare International Airport, so travellers can deplane, grab their bags, and in less than an hour (for $5) be downtime Chicago and ready to explore. The rest of the city is well connected with 8 train lines, running 24/7, and conveniently, travellers can use a preferred contactless method of payment to hop on the train or bus of their choice. Learn more about public transit here.

    For visitors in the summer looking to cruise around downtown, Chicago has a bike share program called Divvy Bikes. Starting at $3.50 for a single ride, it's a great way to see the lake and get some exercise at the same time.

  • How to save money in Chicago

    Our first tip for saving money in Chicago - skip the taxis and Ubers! The transit system is both convenient and affordable, and pretty much accessible anywhere in the city. Like most big American cities, fine dining in Chicago is very, very impressive. But for those not looking to splurge, Chicago's fast casual dining and street food scene are raved about. From pizza and hot dogs to pretzels and pop corn, there are some decadent eats to be enjoyed without breaking the bank. If you're visiting in the summer, one of Chicago's best assets is 100% free - the lake. Chicago's downtown is nestled adjacent to beautiful boardwalks and sandy beaches, and the crisp, clear waters of Lake Michigan. Take a bike ride, take a stroll, jump into a game of beach volleyball, and take it all in.


The perfect summer day in Chicago

Join us on a jam packed day filled with summer fun in the windy city.
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