Flights from Toronto to Chicago from $109
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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.
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Cheap flights from TorontoCheap flights to Chicago
Airline tickets to United States
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.
24.07.2025
Thursday
from $105
MyHolidays
Economy
Found yesterday
Nonstop
1 hours 50 min
Find Flights
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.
Porter Airlines PD 2393
Evening flight
Departure
29.06.25
19:35, Su
Direct
Trip 2 days
Return
01.07.25
22:20, Tu
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.
*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.
Average flight time
01:26 min
Distance
435 mi
The earliest flight
00:00
The latest flight
23:59
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.
- United Airlines: UA 5841, UA 4196, UA 4060
- Air Canada: AC 501, AC 503, AC 7701
- Porter Airlines: PD 383, PD 385, PD 387
- American Airlines: AA 3430, AA 2580, AA 2352
- Aer Lingus: EI 6430
*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 $ 90Chicago 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
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
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
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
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
from $216 20 June 2025
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
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
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
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
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
Find 20 June 2025
Tips for buying a ticket
Toronto – Chicago – Toronto round-trip route are always cheaper than tickets purchased there and back separately.
To start searching for tickets, Specify dates.