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Book flight tickets from Toronto to Chicago starting at ₹ 10,101

Discover our range of affordable one-way and round-trip flights from Toronto to Chicago and kick-start your next adventure today!

  • One way
  • Round-trip
      • Cheapest nonstop
        YTZ10:20
        1h 50m
        Nonstop
        MDW11:10
        Wed, Dec 18|Toronto - Chicago|Porter Airlines
        ₹ 10,101₹ 11,311
        11% OFF
        11% OFF
        ₹ 11,311₹ 10,101

        Choose Porter Airlines flights from Toronto to Chicago. The one-way direct flight with Porter Airlines departs from Billy Bishop Toronto City Airport on Wed, Dec 18, arriving at Midway International Airport. One-way ticket prices start from ₹ 10,101 including taxes and charges.

      • YTZ09:30
        1h 50m
        Nonstop
        MDW10:20
        Sun, Dec 22|Toronto - Chicago|Porter Airlines
        ₹ 10,124₹ 11,311
        10% OFF
        10% OFF
        ₹ 11,311₹ 10,124

        Choose Porter Airlines flights from Toronto to Chicago. The one-way direct flight with Porter Airlines departs from Billy Bishop Toronto City Airport on Sun, Dec 22, arriving at Midway International Airport. One-way ticket prices start from ₹ 10,124 including taxes and charges.

      • YTZ11:10
        1h 50m
        Nonstop
        MDW12:00
        Sat, Dec 14|Toronto - Chicago|Porter Airlines
        ₹ 10,147₹ 11,311
        10% OFF
        10% OFF
        ₹ 11,311₹ 10,147

        Choose Porter Airlines flights from Toronto to Chicago. The one-way direct flight with Porter Airlines departs from Billy Bishop Toronto City Airport on Sat, Dec 14, arriving at Midway International Airport. One-way ticket prices start from ₹ 10,147 including taxes and charges.

      • YTZ11:20
        1h 50m
        Nonstop
        MDW12:10
        Wed, Jan 22|Toronto - Chicago|Porter Airlines
        ₹ 10,217
        ₹ 10,217

        Choose Porter Airlines flights from Toronto to Chicago. The one-way direct flight with Porter Airlines departs from Billy Bishop Toronto City Airport on Wed, Jan 22, arriving at Midway International Airport. One-way ticket prices start from ₹ 10,217 including taxes and charges.

      • YTZ11:20
        1h 50m
        Nonstop
        MDW12:10
        Thu, Jan 9|Toronto - Chicago|Porter Airlines
        ₹ 10,275
        ₹ 10,275

        Choose Porter Airlines flights from Toronto to Chicago. The one-way direct flight with Porter Airlines departs from Billy Bishop Toronto City Airport on Thu, Jan 9, arriving at Midway International Airport. One-way ticket prices start from ₹ 10,275 including taxes and charges.

      • YYZ18:20
        2h
        Nonstop
        ORD19:20
        Wed, Jan 8|Toronto - Chicago|American Airlines
        ₹ 10,287
        ₹ 10,287

        Choose American Airlines flights from Toronto to Chicago. The one-way direct flight with American Airlines departs from Toronto Pearson International Airport on Wed, Jan 8, arriving at O'Hare International Airport. One-way ticket prices start from ₹ 10,287 including taxes and charges.

      • YTZ09:40
        1h 50m
        Nonstop
        MDW10:30
        Thu, Dec 26|Toronto - Chicago|Porter Airlines
        ₹ 10,333
        ₹ 10,333

        Choose Porter Airlines flights from Toronto to Chicago. The one-way direct flight with Porter Airlines departs from Billy Bishop Toronto City Airport on Thu, Dec 26, arriving at Midway International Airport. One-way ticket prices start from ₹ 10,333 including taxes and charges.

      • YTZ11:20
        1h 50m
        Nonstop
        MDW12:10
        Thu, Jan 9|Toronto - Chicago|Air Transat
        ₹ 10,333
        ₹ 10,333

        Choose Air Transat flights from Toronto to Chicago. The one-way direct flight with Air Transat departs from Billy Bishop Toronto City Airport on Thu, Jan 9, arriving at Midway International Airport. One-way ticket prices start from ₹ 10,333 including taxes and charges.

      • YTZ09:30
        1h 50m
        Nonstop
        MDW10:20
        Tue, Dec 31|Toronto - Chicago|Porter Airlines
        ₹ 10,356
        ₹ 10,356

        Choose Porter Airlines flights from Toronto to Chicago. The one-way direct flight with Porter Airlines departs from Billy Bishop Toronto City Airport on Tue, Dec 31, arriving at Midway International Airport. One-way ticket prices start from ₹ 10,356 including taxes and charges.

      • YTZ11:10
        1h 50m
        Nonstop
        MDW12:00
        Sat, Dec 7|Toronto - Chicago|Porter Airlines
        ₹ 10,449
        ₹ 10,449

        Choose Porter Airlines flights from Toronto to Chicago. The one-way direct flight with Porter Airlines departs from Billy Bishop Toronto City Airport on Sat, Dec 7, arriving at Midway International Airport. One-way ticket prices start from ₹ 10,449 including taxes and charges.

      • YTO13:00
        3h 5m
        Nonstop
        CHI14:00
        Wed, Dec 11|Toronto - Chicago|Porter Airlines
        Find More Flights
        Find More Flights

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

Find the best time to fly from Toronto to Chicago

Price trend charts are a great way of tracking how much your flights cost in the lead up to departure and can help you choose when to book your tickets. See how prices to Chicago from Toronto have changed and are set to move below.

Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.

Airlines Flying from Toronto to Chicago

Compare prices from various providers below to understand which option best suits your travel needs, before enjoying a comfortable journey with a trusted airline from Toronto to Chicago.

Porter Airlines
From ₹ 10,101
American Airlines
From ₹ 10,287
Air Transat
From ₹ 10,333
United Airlines
From ₹ 10,926
Air Canada
From ₹ 11,263
Delta Air Lines
From ₹ 11,635
WestJet
From ₹ 13,006

Find more flights and airlines

Alternative Routes from Toronto to Chicago

There are various non-direct routes from Toronto to Chicago which could be cheaper and faster! Check out these alternative options to see if they could work for your trip.

  • Cheapest
    Porter Airlines
    YTZ
    10:20
    1h 50m
    Nonstop
    MDW
    11:10
    Billy Bishop Toronto City Airport - Midway International Airport
    Wed, Dec 18Porter Airlines
    ₹ 10,101
  • American Airlines
    YYZ
    18:20
    2h 0m
    Nonstop
    ORD
    19:20
    Toronto Pearson International Airport - O'Hare International Airport
    Wed, Jan 8American Airlines
    ₹ 10,287
  • Air Canada
    YTZ
    15:25
    5h 30m
    1 transfer
    ORD
    19:55
    Billy Bishop Toronto City Airport - O'Hare International Airport
    Mon, Dec 9Air Canada
    ₹ 11,263
  • Air Canada
    YTZ
    15:25
    5h 30m
    1 transfer
    ORD
    19:55
    Billy Bishop Toronto City Airport - O'Hare International Airport
    Mon, Dec 9Air Canada
    ₹ 11,263
    Find More Flights

FAQ

  • When are flight tickets from Toronto (YTO) to Chicago (CHI) the cheapest?

    Airlines adjust prices for flights from Toronto to Chicago based on the departure date and time of your selection. By analyzing data from all airlines, we've discovered that on Trip.com, you can find the lowest flight prices on Tuesdays, Wednesdays, and Saturdays.

  • How much do flights from Toronto (YTO) to Chicago (CHI) cost?

    According to Trip.com's data, the lowest price is around ₹ 24,141.

  • How long does it take to fly from Toronto (YTO) to Chicago (CHI) and what is the distance?

    It takes around 2 hours 2 minutes to fly from Toronto (YTO) to Chicago (CHI).

  • What is the transportation method from the main airport to downtown in Chicago?

    • The distance from O'Hare International Airport to downtown is about 25 km. It takes about 40 minutes by taxi.
    • The distance from Midway International Airport to downtown is about 14 km. It takes about 30 minutes by taxi.

  • What are the most popular airlines that fly from Toronto (YTO) to Chicago (CHI)?

    Airlines with flights from Toronto (YTO) to Chicago (CHI): American Airlines, Alaska Airlines, Qantas Airways, Qatar Airways, Air Canada and United Airlines.

How to find a cheap flight from Toronto to Chicago

If you don’t know some of the key things to look out for when buying flight tickets, prices can often end up sky high or, worse, sold out! We’ve carefully compiled our six most important steps to help ensure you’re getting the best deals when planning your next journey.
1
Book Early
Once prices are gone, they're gone. Lock in deals while you can!
2
Compare Flight Prices
Compare prices on travel agency and airline websites.
3
Look Out for Deals
Check airline and travel agency websites for latest flight deals
4
Check One-way Fares
Buying two cheap one-way flights can sometimes be a better deal than a round-trip.
5
Try Different Dates
Flying during the week, early in the morning, or late at night can help save money.
6
Use the Trip.com App
Save up to £10 per person when booking your flights on Trip.com

Flight Information from Toronto to Chicago

Cheapest nonstop flight price₹ 10,100
Cheapest round-trip ticket price₹ 16,923
Off-season for travelNovember
Peak season for travelMarch
Flight distance701.97 km
Average flight time2 hours 2 minutes
Popular airlineUnited Airlines

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