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Discover last-minute deals to Chicago. Find suitable one-way and round-trip tickets.

Search for flights to Chicago and check out affordable one-way and round-trip options.

  • One way
  • Round-trip

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

Find Suitable Airport in Chicago

Learn about the different airports in Chicago, find the best flight and transfer options, and plan your journey.

FAQs - Before flights to Chicago

  • How long is the flights to Chicago?
    • Approx. 1 hour 51 minutes to fly from Toronto to Chicago.
    • Approx. 4 hours 27 minutes to fly from Montreal to Chicago.
    • Approx. 3 hours 30 minutes to fly from Calgary to Chicago.
    • Approx. 4 hours 4 minutes to fly from Ottawa to Chicago.
  • How to get cheapest flights to Chicago?
    You can book cheaper flights in the following ways:
    • Search for tickets to a city or airport near Chicago.
    • Look up different airlines that have flights to Chicago.
    • Browse different departure dates from the same month.
    • Filter for different departure times from the same day.
    • Check for discount information on various social media sites.
    • Explore deals and discounts on airline websites.
  • What is the most popular month to visit Chicago?
    Understanding peak and off travel seasons to Chicago can help you arrange your travel plans accordingly. The most popular month to visit Chicago is May. The average price of flight tickets to Chicago in May is CAD 407.
  • When are flight to Chicago cheapest?
    Flight tickets to Chicago are the cheapest in July compared to other months, the average price is CAD 371.
  • What are the major airports in Chicago?
  • What is the transportation method from the main airport to downtown in Chicago?
    • The distance from O'Hare International Airport to downtown is about 25km, by taxi about 40 minutes.
    • The distance from Midway International Airport to downtown is about 14km, by taxi about 30 minutes.
  • Which popular airlines have flights to Chicago?
    Popular airlines with flights to Chicago: Frontier Airlines, Spirit Airlines, and American Airlines.
  • What are some popular attractions in Chicago?
    There are lots of attractions to choose from in Chicago: Groupon Corporate Headquarters (2 km from downtown) , Blake (2 km from downtown) and Orca Aart Gallery (2 km from downtown) are the most popular attractions close to downtown.

Useful Info for Your Flight to Chicago from Canada

Cheapest direct flight priceCAD 163
Cheapest return ticket priceCAD 381
Cheapest monthJanuary
Peak season for travelOctober
Flight distance2,856.1km
Average flight time4 hours 39 minutes
Popular airlineAlaska Airlines
Cheapest monthJuly