Cheap flights from Toronto, Canada
to Chicago, IL
Flights starting at CA$172. Choose between United Airlines, Frontier Airlines, or Air Canada to find the best price.

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Tips to know when travelling to Chicago
Cheapest one-way trip | CA$225 |
---|---|
Cheapest nonstop round-trip | CA$380 |
Cheapest round-trip | CA$417 |
Average round-trip | CA$510 |
Nonstop flights in May | CA$212 – CA$1308 |
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Weekly direct flights
Discover the top airlines offering direct flights from Toronto to Chicago in the next month. You’ll find the number of daily direct flights per airline in the table.
Weekly direct flights for Sun 21.05 - Sat 27.05
Airline | Sun 21.05 | Mon 22.05 | Tue 23.05 | Wed 24.05 | Thu 25.05 | Fri 26.05 | Sat 27.05 |
---|---|---|---|---|---|---|---|
--- | --- | --- | --- | 4 | 7 | 7 | |
--- | --- | --- | --- | --- | --- | --- | |
1 | 2 | 2 | 2 | 2 | 2 | 1 | |
--- | --- | --- | 5 | --- | --- | --- |
Weekly direct flights for Sun 28.05 - Sat 03.06
Airline | Sun 28.05 | Mon 29.05 | Tue 30.05 | Wed 31.05 | Thu 01.06 | Fri 02.06 | Sat 03.06 |
---|---|---|---|---|---|---|---|
12 | 6 | 11 | 11 | 5 | 9 | 10 | |
--- | --- | --- | --- | --- | --- | --- | |
2 | 2 | 2 | 2 | 1 | 2 | 1 | |
--- | --- | --- | --- | --- | --- | --- |
Weekly direct flights for Sun 04.06 - Sat 10.06
Airline | Sun 04.06 | Mon 05.06 | Tue 06.06 | Wed 07.06 | Thu 08.06 | Fri 09.06 | Sat 10.06 |
---|---|---|---|---|---|---|---|
10 | 12 | 11 | 11 | 11 | 8 | 6 | |
1 | --- | --- | --- | --- | --- | --- | |
2 | 2 | 2 | 2 | 2 | 1 | --- | |
--- | --- | --- | --- | --- | --- | --- |
Weekly direct flights for Sun 11.06 - Sat 17.06
Airline | Sun 11.06 | Mon 12.06 | Tue 13.06 | Wed 14.06 | Thu 15.06 | Fri 16.06 | Sat 17.06 |
---|---|---|---|---|---|---|---|
5 | 6 | 9 | 10 | 8 | 3 | 1 | |
--- | --- | 6 | 4 | 3 | 6 | 5 | |
--- | 1 | 2 | 2 | 2 | 2 | 1 | |
--- | --- | --- | --- | --- | --- | --- |
Check-in for a flight from Toronto to Chicago
Name | Carrier code | IATA Code | Passport needed during booking | Online check-in available |
---|---|---|---|---|
United Airlines | UAL | UA | Yes | No |
Frontier Airlines | FFT | F9 | No | Opens 24 days before flight Closes 1 hours before flight |
Air Canada | ACA | AC | Yes | No |
Spirit Airlines | NKS | NK | No | Opens 24 days before flight Closes 1 hours before flight |
WestJet | WJA | WS | No | Opens 24 days before flight Closes 1 hours before flight |
United States COVID-19 travel restrictions

Most travellers from Toronto, YYZ can enter Chicago, ORD, but there are restrictions.
Departure
Travel restrictions |
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Visa requirements |
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Return
Travel restrictions |
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Visa requirements |
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Information is provided as guidance only and accurate at the time of publishing. Always check government websites and airline materials before booking and traveling.
Learn more about COVID-19 restrictions in United States in our dedicated Stories article.
Frequently asked questions
Planning a trip? Thanks to our Virtual Interlining algorithm, we offer billions of route combinations between any A and any B in the world by plane, train, and bus. Find the cheapest routes and best deals for you, as well as the best dates on which to travel.
Explore alternative trips
Flights from Toronto
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Flights to Chicago
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Popular routes
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The nearest countries with flights to Chicago
Here is a list of countries people are flying fromOther destination countries from Toronto
Here is a list of countries people are flying toAirports near Toronto
- Toronto Pearson International
- Billy Bishop Toronto City
- Buffalo Niagara International
- Greater Rochester International
- John C. Munro Hamilton International
- Region of Waterloo International
- Niagara Falls International
- London International
- Bradford Regional
- Erie International