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Cheap flight deals from Toronto to Chicago Starting at AU$142

For as little as AU$142, you can take your next adventure to Chicago without breaking the bank. Choose between one-way and return tickets from Toronto below.

  • One way
  • Round-trip
      • Cheapest nonstop
        YTZ15:50
        1h 50m
        Nonstop
        MDW16:40
        Tue, Apr 1|Toronto - Chicago|Porter Airlines
        AU$142AU$190
        26% OFF
        26% OFF
        AU$190AU$142

        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, Apr 1, arriving at Midway International Airport. One-way Prices start from AU$142 including taxes and charges.

      • YTZ15:50
        1h 50m
        Nonstop
        MDW16:40
        Tue, Mar 11|Toronto - Chicago|Porter Airlines
        AU$147AU$190
        23% OFF
        23% OFF
        AU$190AU$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 Tue, Mar 11, arriving at Midway International Airport. One-way Prices start from AU$147 including taxes and charges.

      • YTZ11:20
        1h 50m
        Nonstop
        MDW12:10
        Wed, Feb 19|Toronto - Chicago|Porter Airlines
        AU$150AU$190
        21% OFF
        21% OFF
        AU$190AU$150

        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, Feb 19, arriving at Midway International Airport. One-way Prices start from AU$150 including taxes and charges.

      • YTZ15:50
        1h 50m
        Nonstop
        MDW16:40
        Tue, Apr 1|Toronto - Chicago|Air Transat
        AU$155
        AU$155

        Choose Air Transat flights from Toronto to Chicago. The one-way direct flight with Air Transat departs from Billy Bishop Toronto City Airport on Tue, Apr 1, arriving at Midway International Airport. One-way Prices start from AU$155 including taxes and charges.

      • YTZ11:20
        1h 50m
        Nonstop
        MDW12:10
        Thu, Feb 27|Toronto - Chicago|Porter Airlines
        AU$156
        AU$156

        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, Feb 27, arriving at Midway International Airport. One-way Prices start from AU$156 including taxes and charges.

      • YTZ09:30
        1h 50m
        Nonstop
        MDW10:20
        Sun, Apr 6|Toronto - Chicago|Porter Airlines
        AU$156
        AU$156

        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, Apr 6, arriving at Midway International Airport. One-way Prices start from AU$156 including taxes and charges.

      • YTZ11:20
        1h 50m
        Nonstop
        MDW12:10
        Fri, Feb 28|Toronto - Chicago|Porter Airlines
        AU$157
        AU$157

        Choose Porter Airlines flights from Toronto to Chicago. The one-way direct flight with Porter Airlines departs from Billy Bishop Toronto City Airport on Fri, Feb 28, arriving at Midway International Airport. One-way Prices start from AU$157 including taxes and charges.

      • YTZ15:50
        1h 50m
        Nonstop
        MDW16:40
        Thu, Mar 13|Toronto - Chicago|Porter Airlines
        AU$158
        AU$158

        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, Mar 13, arriving at Midway International Airport. One-way Prices start from AU$158 including taxes and charges.

      • YTZ09:30
        1h 50m
        Nonstop
        MDW10:20
        Mon, Mar 17|Toronto - Chicago|Porter Airlines
        AU$159
        AU$159

        Choose Porter Airlines flights from Toronto to Chicago. The one-way direct flight with Porter Airlines departs from Billy Bishop Toronto City Airport on Mon, Mar 17, arriving at Midway International Airport. One-way Prices start from AU$159 including taxes and charges.

      • YTZ15:50
        1h 50m
        Nonstop
        MDW16:40
        Thu, Mar 6|Toronto - Chicago|Porter Airlines
        AU$160
        AU$160

        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, Mar 6, arriving at Midway International Airport. One-way Prices start from AU$160 including taxes and charges.

      • YTO01:00 pm
        3h 5m
        Nonstop
        CHI02:00 pm
        Fri, Feb 21|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.

Toronto to Chicago flight time & flight schedules

Flight info.
Departure
Arrival
Weekly Schedule

  1. PD2387

    Porter Airlines

    07:30

    YTZ

    1.8h

    Nonstop

    08:19

    MDW

    SMTWTFS
    Search

  2. TS7060

    Air Transat

    09:30

    YTZ

    1.8h

    Nonstop

    10:20

    MDW

    SMTWTFS
    Search

  3. AA3606

    American Airlines

    13:15

    YYZ

    1.9h

    Nonstop

    14:10

    ORD

    SMTWTFS
    Search

  4. PD2393

    Porter Airlines

    15:35

    YTZ

    1.8h

    Nonstop

    16:24

    MDW

    S--WT-S
    Search
Find more flights and airlines

When is the cheapest time to fly from Toronto to Chicago?

These price trend charts carefully monitor and predict how flight prices from Toronto to Chicago will change. Keep a close eye on them to understand when the best time to buy your tickets is.

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

Frequently Asked Questions

  • When are 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 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 AU$453.

  • How long does it take to fly from Toronto (YTO) to Chicago (CHI)?

    It takes about 2 hours 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, by taxi about 40 minutes.
    • The distance from Midway International Airport to downtown is about 14 km, 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 07:25.

  • 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): Alaska Airlines, American Airlines, United Airlines, Qantas Airways, Air Canada and Qatar Airways.

  • What's the most popular airline for non-stop flights from Toronto (YTO) to Chicago (CHI)?

    United Airlines operates 12 non-stop flights from Toronto (YTO) to Chicago (CHI).

  • How many airports are there in Chicago (CHI)?

How to find a cheap flight from Toronto to Chicago

Understanding the common pitfalls when booking your flight tickets can help you save massively when it comes time to fly. We’ve listed our six essential steps to keep in mind when you’re booking flight tickets to help you find the best price.
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 Info | Toronto to Chicago

Cheapest direct flight priceAU$141
Cheapest return ticket priceAU$232
Off-season for travelApril
Peak season for travelNovember
Flight distance701.97 km
Average flight time2 hours
Popular airlineUnited Airlines

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