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*All fares are shown in USD and were last updated on Feb 22, 2026 at 08:35:40 PM EST. Prices may apply to one-way or round-trip travel and include taxes & fees , fuel surcharges, and service fees . Since fares can change at any time, prices cannot be guaranteed until booking is completed. For more information, please review our terms and conditions , Privacy Policy , and Baggage Policy.
If you want to travel to a city similar to New York and Chicago, you can choose Toronto. It has the typical skyline you are already familiar with in New York and Chicago. But the weather is pleasant owing to the maritime effect Lake Ontario has on the city. The city is picturesque, dotted with creeks and rivers that give it a unique personality. Rawfares allows you to search for cheap flights from Chicago to Toronto.
Toronto is a vibrant, multicultural city packed with unique experiences that make it an appealing destination for travelers from Chicago. One of the city’s standout attractions is the Toronto Islands, just a short ferry ride from downtown. These serene islands offer scenic views, beaches, parks, and walking trails, providing a peaceful escape from the urban hustle of Chicago.
The Hockey Hall of Fame is a must-see for anyone passionate about ice hockey. Visitors can explore interactive exhibits and learn about the game’s rich history.
Another exciting experience in Toronto is catching a baseball game. BlueJays, the Canadian professional baseball team, is based in Toronto. From iconic cultural landmarks to outdoor recreation, Toronto has something for everyone, making it a fantastic destination for travelers looking for cheap flight deals from Chicago to Toronto.
January is the most affordable month to travel. Flight prices to Toronto from Chicago start spiking after July. December is the high season for airlines. Since the prices are dynamic, you need to track the prices of flights so that you get the real picture before you book. Travel booking sites can help you with this.
Make sure you compare the best deals on tickets from Chicago to Toronto, as the prices of airlines may vary. Although Air Canada is one of the cheapest, American Airlines has non-stop flights to Chicago that are comparatively cheaper.
You can get all the deals available for different travel dates on a few booking sites. Making a little adjustment to the dates can help you get a fantastic deal. To score the best deals on flights from Chicago to Toronto, consider flying on Thursdays or Saturdays, as these are generally the cheapest days.
Be sure to book at least a few weeks in advance to secure the lowest fares. Opt for flights with one-stop, as they tend to be less expensive than direct flights. A few routes including Chicago Midway (MDW) to Toronto Island (YTZ) are more cost-effective than others.
Toronto offers a unique experience year-round, with its four distinct seasons each bringing its own unique experience. Spring and early summer (April to June) are especially pleasant, though the city can experience cool afternoons due to the lake breeze from Lake Ontario. The mild weather makes it a great time to explore outdoor attractions like the Toronto Islands or Toronto's parks.
The summer months (July and August) are warm, with temperatures ranging from comfortable to hot, but the lake breeze helps keep the city cool. These months are perfect for attending festivals, and outdoor events and enjoying Toronto's vibrant waterfront.
Fall (September to November) brings cooler temperatures, especially in late September, offering a beautiful display of autumn colors. Winter (December to February) can be cold, with occasional lake-effect snow, but the city still offers winter sports and cozy indoor activities, making it an appealing destination for those who love the winter season.
If you like Chicago and want to experience a similar skyline, you can choose Toronto. Plus, you’ll find the weather pleasant along with clickable pictures of Lake Ontario and Toronto Islands.
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