Cheap flights from Toronto to Chicago

Round-trip
Economy
Toronto (YTO)
Chicago (CHI)
Depart
Return
Any month
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The best prices from Toronto to Chicago are usually found in April or March, booked 46 days in advance, depart on a Wednesday or Thursday and return on a Sunday

How to find the cheapest flight from
Toronto (YTO) to Chicago (CHI)

All the information you need to plan the best YTO to CHI flight in 2022: compare Toronto to Chicago flight prices with the expected peak season, weather and rainfall in Chicago.
YTO - CHI
Price
C$ 224 - C$ 279
CHI
Temperature
-5 - 23 °C
CHI
Precipitation
43 - 125 mm

Popular in

January

High demand for flights, 9% potential price rise

Cheapest in

April

Best time to find cheap flights, 11% potential price drop

Round-trip from

C$ 280

From Toronto (YTO) to Chicago (CHI)

One-way from

C$ 109

One-way flight from Toronto (YTO) to Chicago (CHI)

Flight route prices based on searches on Cheapflights within the last 3 days, monthly prices based on aggregated historical data.
What is the cheapest day to fly round-trip from Toronto to Chicago?

Tuesday is generally a great day to depart. Flying on this day could help you save up to 8%.

When is the cheapest time to fly from Toronto to Chicago (YTO - CHI)?

Unlike in the evening, when flights are generally more expensive, you can save up to 9% on flights from Toronto to Chicago by exploring options for tickets at noon.

What is the cheapest month to fly from Toronto to Chicago?

April is one of the best times of the year to fly to Chicago from Toronto. Prices for April average C$ 316 per person but you can even find prices for as low as C$ 239. The most expensive prices can be found in the month of January. Opting for a April flight can save you 10% on your journey compared to booking in April

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

Find a great deal and save up to 86% by booking at least 34 days prior to your desired departure date, rather than waiting until the week of travel. According to our data, there are a number of flights available from Toronto to Chicago within the next two weeks, with the cheapest ticket starting at C$ 434.

Cheap flights from Toronto to Chicago in January, February 2022

The best prices found for YTO to CHI flights for January, February
21 Feb - 25 Feb
C$ 257pp
YTZ
Toronto Island
Porter Airlines
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Porter Airlines
Direct
YTZ
Toronto Island
16 Feb - 23 Feb
C$ 259pp
YTZ
Toronto Island
Air Canada
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
 
1 STOP
YTZ
Toronto Island
11 Feb - 13 Feb
C$ 259pp
YTZ
Toronto Island
Porter Airlines
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Porter Airlines
Direct
YTZ
Toronto Island

Toronto to Chicago 2022 flight deals

Cheap flights to Chicago from Toronto found for this year
4 Jun - 7 Jun
C$ 204pp
YYZ
Toronto Pearson Intl
Flair Airlines
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Flair Airlines
Direct
YYZ
Toronto Pearson Intl
10 Sep - 13 Sep
C$ 205pp
YYZ
Toronto Pearson Intl
Flair Airlines
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Flair Airlines
Direct
YYZ
Toronto Pearson Intl
20 Apr - 20 Apr
C$ 251pp
YYZ
Toronto Pearson Intl
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Direct
YYZ
Toronto Pearson Intl

Direct flights to Chicago from Toronto

Save time with Toronto to Chicago direct flight deals
4 Jun - 7 Jun
C$ 204pp
YYZ
Toronto Pearson Intl
Flair Airlines
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Flair Airlines
Direct
YYZ
Toronto Pearson Intl
21 Feb - 25 Feb
C$ 257pp
YTZ
Toronto Island
Porter Airlines
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Porter Airlines
Direct
YTZ
Toronto Island
11 Feb - 13 Feb
C$ 259pp
YTZ
Toronto Island
Porter Airlines
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Porter Airlines
Direct
YTZ
Toronto Island

Last minute flights from Toronto to Chicago

Late deals on round-trip flights to Chicago from Toronto, departing today and this week
26 Jan - 29 Jan
C$ 277pp
YYZ
Toronto Pearson Intl
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
YYZ
Toronto Pearson Intl
25 Jan - 26 Jan
C$ 301pp
YYZ
Toronto Pearson Intl
American Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
YYZ
Toronto Pearson Intl
27 Jan - 31 Jan
C$ 305pp
YYZ
Toronto Pearson Intl
American Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
YYZ
Toronto Pearson Intl

One-way flights to Chicago from Toronto

The cheapest one-way flights from Toronto to Chicago
2:50 a.m. - 3:40 a.m.
Flair Airlines
Direct
1h 50m
YYZ - ORD
Flair Airlines
C$ 109
mytrip.com
2:55 a.m. - 4:08 a.m.
Multiple Airlines
2 stops
26h 13m
YYZ - ORD
Multiple Airlines
C$ 162
Gotogate
9:25 a.m. - 10:15 a.m.
Porter Airlines
Direct
1h 50m
YTZ - MDW
Porter Airlines
C$ 164
SmartFares

Related info for your journey

Useful info, stats and facts about <span class="emphasized">Toronto</span> to <span class="emphasized">Chicago</span> flights.

Flight FAQs

From Toronto to Chicago

Which airlines flying from Toronto to Chicago have flexible cancellations due to COVID-19?

Air Canada, American Airlines, and United Airlines are some of the carriers that may have flexible cancellation policies. You can use our site to filter for other airlines that may also have this kind of flexibility.

Can I find flights from Toronto to Chicago for under C$ 300 on Cheapflights?

Yes, there are multiple flights from Toronto to Chicago for under C$ 300. The cheapest flight booked recently is on Flair Airlines for just C$ 204, but on average you can expect to pay C$ 260.

Are there direct flights from Toronto to Chicago for under C$ 300 on Cheapflights?

Cheapflights has 20 direct flights from Toronto to Chicago under C$ 300. A good price for a direct flight from Toronto to Chicago is less than C$ 267.

Are there last-minute flights available from Toronto to Chicago for under C$ 300?

There are currently 20+ open flights from Toronto to Chicago within the next 7 days for less than C$ 300.

What are the cheapest airlines flying from Toronto to Chicago round-trip?

Our cheapest airline available from Toronto to Chicago is Flair Airlines. Our recent data shows that you can find tickets from as low as C$ 204 on this airline. Additional options worth looking into are Porter Airlines and Air Canada, starting at C$ 257 and C$ 259 round-trip. Users have found that Flair Airlines is 35% cheaper than the other options available to this destination.

What are the cheapest airlines to fly from Toronto to Chicago one-way?

The cheapest airlines for a one-way flight from Toronto to Chicago are Flair Airlines (C$ 100), Air Canada (C$ 132), and Porter Airlines (C$ 155).

What are the most popular airlines that fly from Toronto to Chicago?

The most popular airlines flying from Toronto to Chicago are Major Airline, American Airlines and Air Canada. Something to consider prior to booking your flight.

What are the cheapest flights from Toronto to Chicago?

On average you can expect to pay C$ 194 for a flight from Toronto to Chicago. The cheapest flight overall is C$ 140 while the most popular route, (Toronto Pearson Intl - Chicago O'Hare Intl) is currently priced at C$ 204.

What are the most popular routes from Toronto to Chicago?

When deciding which route to take from Toronto to Chicago consider Toronto Pearson Intl - Chicago O'Hare Intl, Toronto Island - Chicago Midway or Toronto Island - Chicago O'Hare Intl as they are the most popular.

What are the most reliable airlines from Toronto to Chicago?

Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Toronto to Chicago on time: ANA (100%), Republic Airways (100%), Envoy Air (93%).

What airports serve Toronto to Chicago flights?

Flying out of Toronto to go to Chicago, you’ll show up to board your flight at Pearson International Airport in Toronto. Your flight will be heading for either Chicago O’Hare or Chicago Midway International Airport. You’ll find a variety of options for this route. You can fly direct, with one-stop, or more. There is a large range of prices for these flights.O’Hare International Airport is on the northwest side of the city in Chicago. It’s about 14 miles away from the city centre. The airport was built to take over for Midway originally. It’s a busy airport that is a hub for major airlines like United and American Airlines.Midway International Airport used to be the main airport in Chicago until O’Hare came along. This airport is still the second busiest one in the state of Illinois though. This is a major hub for Southwest Airlines.

Which airlines fly directly from Toronto to Chicago?

You can find a lot of direct flights from Toronto to Chicago. American Airlines has a few from Pearson to O’Hare. They’re about two hours long. Air Canada flies the same route. United also flies non-stop between Pearson and O’Hare.

What are the stopover options between Toronto to Chicago?

American Airlines has one-stop flights that land in Charlotte on the way to Chicago. This stopover varies in the time it adds to your travel day. You could be looking at six and a half hours, but also up to eleven hours. Delta makes a stopover in Detroit on the way to either Midway or O’Hare. These flights are only a few hours longer than the direct flights. Air Canada has a route that goes through Montreal before landing at O’Hare.

Do I need a passport or visa to fly from Toronto to Chicago?

While you do need your passport because you’re passing over the border into the US, you do not need a visa if you’re only going for a leisure trip. If you will be working or going to school, or investing on your trip, then you will need some kind of visa.

COVID Restrictions

View COVID Travel Restrictions for Chicago, IL

Do I need a COVID test to fly to Chicago from Toronto?

Information is based on travel restrictions from Toronto to Chicago

Most visitors from Toronto need to provide a negative COVID-19 test result and/or quarantine to enter Chicago.

COVID-19 testing requirements
Visitors from Toronto must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 24 hours before departing to Chicago.

Quarantine requirements
Visitors from Toronto are not required to quarantine after entering Chicago.

Do I need a test to fly back to Toronto from Chicago?

Returning to Toronto from Chicago

COVID-19 testing requirements
Visitors from Chicago must present a negative RT-PCR (NAAT) test taken 72 hours before departing to Toronto.

Quarantine requirements
Visitors from Chicago are not required to quarantine after entering Toronto.

Hide COVID Travel Restrictions for Chicago, IL

Destination information for Chicago

Things to know before you go - useful duration and weather info for your trip from Toronto to Chicago.
Today's exchange rate
C$ 1 = $0.81
Flight duration from Toronto to Chicago
1h 47m
Average temperature for January in Chicago
1.0 °C
Avg rainfall for January in Chicago
17.0 mm

Airports servicing Toronto

Toronto Island (YTZ)
Hamilton (YHM)
Kitchener-Waterloo (YKF)

Airports servicing Chicago

Midway (MDW)
Rockford (RFD)

Top 6 airlines flying from Toronto to Chicago

The chart below displays the airlines Cheapflights users travelling from Toronto to Chicago choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
Airline Cheapest Average Flexibility On-time COVID-19 safety
American Airlines
C$ 163 C$ 432 No cancel fee 71%
Search American Airlines flights
Air Canada
C$ 176 C$ 373 No cancel fee 67%
Search Air Canada flights
Porter Airlines
C$ 214 C$ 357 No cancel fee 52%
Search Porter Airlines flights
United Airlines
C$ 220 C$ 389 No cancel fee 69%
Search United Airlines flights
WestJet
C$ 221 C$ 463 No cancel fee 60%
Search WestJet flights
Delta
C$ 258 C$ 481 No cancel fee N/A
Search Delta flights

Hourly flight availability from Toronto to Chicago

See what time of day planes typically take off from Toronto towards Chicago.
Morning 6 AM to noon 40% of YTO to US-CHI departures
Afternoon Noon to 6 PM 39% of YTO to US-CHI departures
Early morning Midnight to 6 AM 16% of YTO to US-CHI departures
Evening 6 PM to midnight 5% of YTO to US-CHI departures
Midnight
6 AM
Noon
6 PM
Weekly flight availability
from Toronto to Chicago
See how many times per day planes take to the skies headed from Toronto to Chicago.
Sunday
26 daily flights
Monday
30 daily flights
Tuesday
29 daily flights
Wednesday
30 daily flights
Thursday
27 daily flights
Friday
30 daily flights
Saturday
23 daily flights
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