Airfare Deals Toronto to Chicago

On HolidayPrice.com you will find 5 direct and 1 connecting flights from Toronto to Chicago at a price of from $109. You can compare airfare deals from airlines and multiple travel sites, book and save on cheap plane tickets and last minute offers. Also check out YTO - CHI flight schedule to find best flight time, convenient departure and arrival airports.

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The cost of airline tickets from Toronto to Chicago (United States) and back without transfers can be found with the help of the calendar. Specify the search parameters: one way or round-trip, payment currency, click on the month/day you need and we will search for flights to Chicago.

One way flight from Toronto to Chicago

Below are the prices of tickets for direct one-way flights from Toronto to Chicago. The cheapest flight from Toronto to Chicago starts from $109 – the departure date for this flight is 31 July 2025.

Sort by: Departure dateCheap flightsFast flightsDirect flights
24.07.2025 Thursday
from $105 MyHolidays
Economy Found yesterday
Nonstop 1 hours 50 min
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25.07.2025 Friday
from $108
Economy Found today
Nonstop 0 hours 0 min
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30.07.2025 Wednesday
from $108
Economy Found today
Nonstop 0 hours 0 min
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29.07.2025 Tuesday
from $108
Economy Found today
Nonstop 0 hours 0 min
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28.07.2025 Monday
from $108
Economy Found today
Nonstop 0 hours 0 min
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27.07.2025 Sunday
from $108
Economy Found today
Nonstop 0 hours 0 min
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26.07.2025 Saturday
from $108
Economy Found today
Nonstop 0 hours 0 min
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18.07.2025 Friday
from $108
Economy Found today
Nonstop 0 hours 0 min
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17.07.2025 Thursday
from $108
Economy Found today
Nonstop 0 hours 0 min
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16.07.2025 Wednesday
from $108
Economy Found today
Nonstop 0 hours 0 min
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14.07.2025 Monday
from $108
Economy Found today
Nonstop 0 hours 0 min
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23.07.2025 Wednesday
from $108
Economy Found today
Nonstop 0 hours 0 min
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21.07.2025 Monday
from $108
Economy Found today
Nonstop 0 hours 0 min
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11.07.2025 Friday
from $108
Economy Found today
Nonstop 0 hours 0 min
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19.07.2025 Saturday
from $108
Economy Found today
Nonstop 0 hours 0 min
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20.07.2025 Sunday
from $108
Economy Found today
Nonstop 0 hours 0 min
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12.07.2025 Saturday
from $108
Economy Found today
Nonstop 0 hours 0 min
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22.07.2025 Tuesday
from $108
Economy Found today
Nonstop 0 hours 0 min
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13.07.2025 Sunday
from $108
Economy Found today
Nonstop 0 hours 0 min
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15.07.2025 Tuesday
from $108
Economy Found today
Nonstop 0 hours 0 min
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31.07.2025 Thursday
from $110 Biletix
Economy Found 2025-06-09
Nonstop 1 hours 50 min
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10.07.2025 Thursday
from $110 Biletix
Economy Found 2025-06-09
Nonstop 1 hours 49 min
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*Prices include: baggage, hand luggage, airline fees and charges.

Round trip from Toronto to Chicago

You can buy a round-trip ticket from Toronto to Chicago (United States) and back using the table below. The best offer starts from $243, the flight dates are: there on 29 June 2025 year and back on 01 July 2025 year.

Sort by: Departure dateCheap flightsTrip timeDirect flights
Porter Airlines PD 2393 Evening flight
Departure 29.06.25 19:35, Su
Direct Trip 2 days
Return 01.07.25 22:20, Tu
*Prices include: baggage, hand luggage, airline fees and charges.
Not found promotions and sales.

Flight Schedule Toronto to Chicago 2025

The current flight schedule for the route from Toronto to Chicago for today, tomorrow and the next few days. This schedule will help you decide on the time of departure and arrival, the airline, the flight number and the day of the week.

More than 5 flights every day, from 1hours 51min. Local departure and arrival times are indicated.
09:0010:04
United Airlines UA1538 United Airlines UA1538
YYZ → ORD
Mo Tu We Th Fr Sa Su
Check price
12:2013:11
Air Canada AC503 Air Canada AC503
YYZ → ORD
Mo Tu We Th Fr Sa Su
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14:0014:51
Air Canada AC505 Air Canada AC505
YYZ → ORD
Mo Tu We Th Fr Sa Su
Check price
15:3016:35
United Airlines UA2364 United Airlines UA2364
YYZ → ORD
Mo Tu We Th Fr Sa Su
Check price
18:4019:37
Air Canada AC509 Air Canada AC509
YYZ → ORD
Mo Tu We Th Fr Sa Su
Check price
18:4519:42
Air Canada AC509 Air Canada AC509
YYZ → ORD
- - - - - Sa -
Check price

*Schedule is indicated only for direct scheduled flights and low-cost airlines.

Flight Information

Flying to Chicago from Toronto takes 01:26 minutes (excluding transfers). The distance between Toronto and Chicago is 435 miles (700 kilometers). Planes depart from Toronto between 00:00 and 23:59. The fastest flight from the company United Airlines with flight number UA 547. Flies for just 01:41 minutes with departure from Pearson and arrival in O'Hare.

time

Average flight time

01:26 min

distance

Distance

435 mi

The earliest flight

The earliest flight

00:00

The latest flight

The latest flight

23:59

Airplane

The fastest flight

01:41

Airlines

Direct flight

There are 5 airlines that fly directly from Toronto to Chicago. The most popular company carrying out non-stop flights is United Airlines.

*Flight number

Flights with Transfers

Flights with transfers from Toronto to Chicago can be bought from 1 airlines:

  • Air Canada: Pittsburgh

*Transit cities

Airports

Airports serving the air communication between Toronto and Chicago. You can fly to Chicago from 2 Toronto airports. Planes arrive at 2 airport in Chicago.

Toronto airports:

Pearson  ~ 20 km* from $ 74Toronto City Centre Airport  ~ 3 km* from $ 90

Chicago airports:

O'Hare  ~ 25 km* from $ 74Chicago Midway  ~ 14 km* from $ 90

*Distance from the airport to the city center

Aircraft

You can fly from Toronto to Chicago on board of 5 airlines that utilize 14 aircraft models.

  • Airbus A319
  • Airbus A320
  • Boeing 737-700
  • Boeing 737-800
  • Boeing 737-900
  • Canadair reg jet 700
  • Canadair regional jet
  • DeHavilland Dash 8 Q400
  • Embraer 170
  • Embraer 175
  • Embraer 190
  • Embraer EMB 175
  • Embraer ERJ-135/140/145 Regional Jet
  • Embraer RJ145

Connecting cities

The list of cities on transfer flights to Chicago from Toronto. The best options are to fly through: Pittsburgh.

Cheap airline tickets from Toronto to United States

Here is a list of flights from Toronto to United States purchased on HolidayPrice.com in the past 48 hours. If you find an interesting offer for cheap tickets, do not delay your purchase, prices change every 15 minutes.

Toronto - New York AC 728 Air Canada Embraer 190
04:05 Pearson
in a way 1 hours 24 min Direct
05:29 LaGuardia
Flights
from $105
10 July 2025
Toronto - Los Angeles AC 791 Air Canada Boeing 787-900
15:00 Pearson
in a way 5 hours 6 min Direct
20:06 Los Angeles
Flights
Find
20 June 2025
Toronto - Miami WO 820 World Airways Boeing 737-800
16:05 Hamilton
in a way 3 hours 1 min Direct
19:06 Fort Lauderdale Executive Airport
Flights
from $164
01 July 2025
Toronto - Chicago UA 547 United Airlines Boeing 737-800
15:15 Pearson
in a way 1 hours 41 min Direct
16:56 O'Hare
Flights
from $109
31 July 2025
Toronto - San Francisco AC 737 Air Canada Boeing 787-900
15:00 Pearson
in a way 5 hours 0 min Direct
20:00 San Francisco
Flights
from $216
20 June 2025

All flights from Toronto

Flights from Canada to Chicago

Here are the cheapest flight bookings from Canada to Chicago made by users of our website. If you didn’t find your flight destination, use the search bar at the top of the page.

Toronto - Chicago UA 547 United Airlines Boeing 737-800
15:15 Pearson
in a way 1 hours 41 min Direct
16:56 O'Hare
Flights
from $109
31 July 2025
Vancouver - Chicago UA 664 United Airlines Airbus A320
17:00 Vancouver
in a way 3 hours 59 min Direct
20:59 O'Hare
Flights
Find
20 June 2025
Montreal - Chicago AC 7599 Air Canada Embraer EMB 175
02:50 St. Hubert Airport
in a way 2 hours 10 min Direct
05:00 O'Hare
Flights
from $279
14 June 2025
Ottawa - Chicago UA 5387 United Airlines Embraer 175
14:15 Ottawa/Macdonald-Cartier
in a way 2 hours 19 min Direct
16:34 O'Hare
Flights
from $230
20 June 2025
Edmonton - Chicago DL 4442 Delta Air Lines Canadair Regional Jet 900
21:55 Edmonton
in a way 6 hours 18 min 1 Stopover
04:13 O'Hare
Flights
Find
20 June 2025

All flights to Chicago

Tips for buying a ticket

Toronto – Chicago – Toronto round-trip route are always cheaper than tickets purchased there and back separately.

Cheap flights from Toronto to Chicago
Chicago city

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