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Cheap Flights from Toronto to Chicago starting at S$ 152

We've found these cheap flights for you. You can book one-way or return flight tickets.

  • One way
  • Round-trip

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

Cheapest time to fly from Toronto to Chicago

We monitor flight fares to help you find the best deals effortlessly

Displayed prices are calculated based on the lowest average weekly prices of the corresponding route on Trip.com.
Cheapest Airlines flying from Toronto to Chicago

Compare prices, find the option that best suits your travel needs, and enjoy a comfortable journey with a trusted airline.

Lynx Air
From S$ 152
United Airlines
From S$ 177
Porter Airlines
From S$ 200
Air Canada
From S$ 229
Flair Airlines
From S$ 262
Westjet
From S$ 265
Sun Country Airlines
From S$ 276
American Airlines
From S$ 363
Delta Air Lines
From S$ 375
Canada Jetlines
From S$ 388
ANA airlines

Find more flights and airlines

Alternative Routes from Toronto to Chicago

Searching for potential routes that might be cheaper and faster? Check out these alternative flights from Toronto to Chicago.

  • Cheapest
    Lynx Air
    YYZ
    12:10
    13h 49m
    1 transfer
    ORD
    00:59
    Toronto Pearson International Airport - O'Hare International Airport
    Tue, May 14Lynx Air
    S$ 152
  • Lynx Air
    YYZ
    07:45
    15h 4m
    1 transfer
    MDW
    21:49
    Toronto Pearson International Airport - Midway International Airport
    Fri, Apr 26Lynx Air
    S$ 183
  • Porter Airlines
    YTZ
    10:30
    1h 47m
    Direct
    MDW
    11:17
    Billy Bishop Toronto City Airport - Midway International Airport
    Sun, Apr 14Porter Airlines
    S$ 200
  • Porter Airlines
    YTZ
    10:30
    1h 47m
    Direct
    MDW
    11:17
    Billy Bishop Toronto City Airport - Midway International Airport
    Sun, Apr 14Porter Airlines
    S$ 200
    Find More Flights

Frequently Asked Questions

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

    Airlines adjust prices for flights from Toronto to Chicago based on the date and time of your booking. By analyzing data from all airlines, on Trip.com, you can find the cheapest flight prices on Tuesdays, Wednesdays, and Saturdays.
  • How much is a flight from Toronto (YTO) to Chicago (CHI) cost?

    According to Trip.com's data, the lowest price is around S$ 394.
  • How long is a flight from Toronto (YTO) to Chicago (CHI)?

    It takes about 1 hour 54 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 25km, by taxi about 40 minutes.
    • The distance from Midway International Airport to downtown is about 14km, by taxi about 30 minutes.
  • What time does the earliest flight from Toronto to Chicago depart?

    The earliest flight departs from Toronto (YYZ) at 06:30 and arrives in Chicago (ORD) at 07:26.
  • What time does the latest flight from Toronto to Chicago depart?

    The latest flight departs from Toronto (YYZ) at 21:00 and arrives in Chicago (ORD) at 22:02.
  • What are the most popular airlines that fly from Toronto (YTO) to Chicago (CHI)?

    Airlines with flights from Toronto (YTO) to Chicago (CHI): United Airlines, Air Canada, British Airways, Alaska Airlines, American Airlines, Qatar Airways and Royal Jordanian.
  • What's the most popular airline for direct flights from Toronto (YTO) to Chicago (CHI)?

    United Airlines operates 12 direct flights from Toronto (YTO) to Chicago (CHI).
  • How many airports in Chicago?

Find cheapest flight ticket from Toronto to Chicago

Cheapest direct flight price

S$ 151

Cheapest return ticket price

S$ 256

Cheapest month

February

Peak season for travel

September