When did momondo last update prices for flights from Toronto to Chicago?

Prices for flights from Toronto to Chicago are refreshed on a daily basis.

How old do you have to be to fly from Toronto to Chicago?

The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Toronto to Chicago.

What documentation or ID do you need to fly to Chicago?

The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's licence and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

R6 227 Cheap Flights from Toronto to Chicago in 2025/26

1 adult

0 bags

Save money when you book flights with momondo

Big names, great deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? Instantly customise your results.

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

Find the cheapest flights from Toronto to Chicago

Round-trip

One-way

Cheap return flights

YYZ-ORD

2h 15mdirect

ORD-YYZ

1h 35mdirect

American Airlines

Find Deal

YYZ-ORD

2h 15mdirect

ORD-YYZ

1h 45mdirect

Qatar Airways

Find Deal

YYZ-ORD

2h 06mdirect

ORD-YYZ

1h 48mdirect

Air Canada

Find Deal

YYZ-ORD

2h 15mdirect

ORD-YYZ

1h 51mdirect

Japan Airlines

Find Deal

YYZ-ORD

1h 55mdirect

ORD-YYZ

1h 53mdirect

Emirates

Find Deal

YYZ-ORD

2h 05mdirect

ORD-YYZ

1h 48mdirect

Egyptair

Find Deal

YYZ-ORD

2h 06mdirect

ORD-YYZ

1h 48mdirect

Copa Airlines

Find Deal

YYZ-ORD

2h 06mdirect

ORD-YYZ

1h 48mdirect

Air New Zealand

Find Deal

YYZ-ORD

2h 05mdirect

ORD-YYZ

1h 48mdirect

United Airlines

Find Deal

YYZ-ORD

2h 15mdirect

ORD-YYZ

1h 35mdirect

Alaska Airlines

Find Deal

YYZ-ORD

2h 15mdirect

ORD-YYZ

1h 35mdirect

Qantas Airways

Find Deal

YYZ-ORD

2h 15mdirect

ORD-YYZ

1h 50mdirect

Royal Jordanian

Find Deal

YYZ-ORD

2h 00mdirect

ORD-YYZ

1h 45mdirect

Iberia

Find Deal

YYZ-ORD

2h 05mdirect

ORD-YYZ

1h 50mdirect

ANA

Find Deal

How to get the cheapest flight ticket from Toronto to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Other information

What is the cheapest month to fly to Chicago?

The month of July is, on average, the cheapest month to fly to Chicago from Toronto, with most prices found around R3 764. If you are unable to visit Chicago during the month of July, then departing from Toronto during the month June is also very affordable. Most momondo users find prices during this month for around R3 902.

What is the cheapest day to depart on your flight to Chicago?

On average, the least expensive day to fly to Chicago from Toronto is on a Saturday. momondo users have found tickets for Saturday departures for as low as R6 644. However, this price may fluctuate depending on the airline, the season, and holidays. Be sure to avoid booking your departure on a Wednesday as prices are generally higher than usual. According to our data, the average ticket price to Chicago on Wednesday is R15 095.

What is the cheapest time of day to depart on your flight to Chicago?

Our data shows that the cheapest Toronto to Chicago flights are usually those with departure times in the morning. Our users have found flights to Chicago in the morning for as low as R12 794. Try not to purchase tickets in the afternoon because they tend to be around R18 564. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Toronto to Chicago flight route?

Fly from Toronto Pearson Intl to Chicago O'Hare Intl for the best Toronto - Chicago flight prices

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from Toronto when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around R5 060 when searching weeks before you fly. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Toronto for as low as R3 746 on momondo.

What cabin class options are available on Toronto to Chicago flights?

There is only 1 cabin class available to choose from on Toronto to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

How have Toronto to Chicago flight prices changed over time?

As of September 2025, prices for Toronto to Chicago flights are approximately 28% cheaper when compared to flights at the same time last year.

When to book flights from Toronto to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Toronto to Chicago according to our flight data. Find out which month and days have the cheapest flights.

Estimated return price

Cheap Toronto to Chicago (YTO to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Toronto to Chicago

Direct flights	None

There are no direct flights from Toronto to Chicago. There are no popular flight routes from Toronto to Chicago.

Search flight deals

How far is Toronto to Chicago by plane?
The straight-line distance from Toronto to Chicago is 700,6 km.
When did momondo last update prices for flights from Toronto to Chicago?
Prices for flights from Toronto to Chicago are refreshed on a daily basis.
How old do you have to be to fly from Toronto to Chicago?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Toronto to Chicago.
What documentation or ID do you need to fly to Chicago?
The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's licence and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
What is the most popular plane model from Toronto to Chicago?
momondo data reveals that the most frequently booked plane model on the route from Toronto to Chicago is De Havilland (Bombardier) DHC-8-400 Dash 8Q, representing 19,88% of all bookings. The subsequent popular models are Embraer 175 (Enhanced Winglets) at 14,77%, Boeing 737-800 at 12,37%, and Embraer 175 at 8,18%.

Hammond

Why use momondo?

Why should I use momondo to find a flight deal from Toronto to Chicago?

It is quick and easy to find Toronto to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

Can I find flights from Toronto to Chicago with flexible booking policies on momondo?

Yes. All flights to Chicago from Toronto on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Toronto to Chicago?

momondo provides multiple filters to help you find the best flight to Chicago from Toronto. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Toronto to Chicago right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Chicago from Toronto. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.