Cheap flights from Toronto Island to Chicago

Round-trip
Economy
Toronto (YTZ)
Chicago (CHI)
Depart
Return
Any month
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How to find the cheapest flight from
Toronto Island (YTZ) to Chicago (CHI)

All the information you need to plan the best YTZ to CHI flight in 2021: compare Toronto Island to Chicago flight prices with the expected peak season, weather and rainfall in Chicago.
YTZ - CHI
Price
C$ 211 - C$ 685
CHI
Temperature
-5 - 23 °C
CHI
Precipitation
43 - 125 mm

Popular in

January

High demand for flights, 56% potential price rise

Cheapest in

November

Best time to find cheap flights, 29% potential price drop

Round-trip from

C$ 269

From Toronto Island to Chicago (CHI)

One-way from

C$ 153

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

Flight route prices based on searches on Cheapflights within the last 3 days, monthly prices based on aggregated historical data.
When is the cheapest time to fly from Toronto Island Airport to Chicago (YTZ - CHI)?

When flying from Toronto Island Airport to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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

Due to multiple factors, expect to potentially pay more when booking in January. For low rates, April can be a great choice for travel to Chicago. Flights to Chicago from Toronto Island Airport in April are about C$ 323 on average during April, but can be found for as low as C$ 244.

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

Travellers have found it’s best to book a flight 34 days in advance to save up to 86% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 34 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Toronto Island Airport to Chicago 1-2 weeks in advance for as low as C$ 443, or C$ 600 for flights within the next 24 hours.

Cheap flights from Toronto Island to Chicago in December, January 2022

The best prices found for YTZ to CHI flights for December, January
1 Jan - 4 Jan
C$ 268pp
YTZ
Toronto Island
Porter Airlines
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Porter Airlines
Direct
YTZ
Toronto Island
17 Dec - 25 Dec
C$ 276pp
YTZ
Toronto Island
Porter Airlines
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Porter Airlines
Direct
YTZ
Toronto Island
20 Dec - 30 Dec
C$ 277pp
YTZ
Toronto Island
Porter Airlines
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Porter Airlines
Direct
YTZ
Toronto Island

Toronto Island to Chicago 2022 flight deals

Cheap flights to Chicago from Toronto Island found for this year
17 Dec - 25 Dec
C$ 276pp
YTZ
Toronto Island
Porter Airlines
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Porter Airlines
Direct
YTZ
Toronto Island
20 Dec - 30 Dec
C$ 277pp
YTZ
Toronto Island
Porter Airlines
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Porter Airlines
Direct
YTZ
Toronto Island
20 Dec - 25 Dec
C$ 280pp
YTZ
Toronto Island
Porter Airlines
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Porter Airlines
Direct
YTZ
Toronto Island

Direct flights to Chicago from Toronto Island

Save time with Toronto Island to Chicago direct flight deals
1 Jan - 4 Jan
C$ 268pp
YTZ
Toronto Island
Porter Airlines
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Porter Airlines
Direct
YTZ
Toronto Island
17 Dec - 25 Dec
C$ 276pp
YTZ
Toronto Island
Porter Airlines
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Porter Airlines
Direct
YTZ
Toronto Island
20 Dec - 30 Dec
C$ 277pp
YTZ
Toronto Island
Porter Airlines
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Porter Airlines
Direct
YTZ
Toronto Island

Last minute flights from Toronto Island to Chicago

Late deals on round-trip flights to Chicago from Toronto Island, departing today and this week
12 Dec - 24 Dec
C$ 377pp
YTZ
Toronto Island
Porter Airlines
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Porter Airlines
Direct
YTZ
Toronto Island
12 Dec - 10 Jan
C$ 393pp
YTZ
Toronto Island
Porter Airlines
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Porter Airlines
Direct
YTZ
Toronto Island
10 Dec - 21 Dec
C$ 394pp
YTZ
Toronto Island
Porter Airlines
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Porter Airlines
Direct
YTZ
Toronto Island

One-way flights to Chicago from Toronto Island

The cheapest one-way flights from Toronto Island to Chicago
4:00 a.m. - 4:50 a.m.
Porter Airlines
Direct
1h 50m
YTZ - MDW
Porter Airlines
C$ 153
SmartFares
10:40 a.m. - 11:30 a.m.
Porter Airlines
Direct
1h 50m
YTZ - MDW
Porter Airlines
C$ 161
Travelgenio
10:40 a.m. - 11:30 a.m.
Porter Airlines
Direct
1h 50m
YTZ - MDW
Porter Airlines
C$ 169
Kiwi.com

Related info for your journey

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

Flight FAQs

From Toronto Island to Chicago

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

Some of the carriers operating flights from Toronto Island to Chicago that may be offering flexible cancellation policies are Porter Airlines and Air Canada. Our site will let you filter for all airlines offering greater flexibility due to COVID-19.

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

Yes, there are multiple flights from Toronto Island Airport to Chicago for under C$ 300. The cheapest flight booked recently is on Porter Airlines for just C$ 268, but on average you can expect to pay C$ 291.

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

Cheapflights has 20 direct flights from Toronto Island Airport to Chicago under C$ 300. A good price for a direct flight from Toronto Island Airport to Chicago is less than C$ 291.

Are there last-minute flights available from Toronto Island Airport to Chicago for under C$ 400?

There are currently 20+ open flights from Toronto Island Airport to Chicago within the next 7 days for less than C$ 400.

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

According to our current data, Porter Airlines (C$ 268), and Air Canada (C$ 301) offers the cheapest pricing from Toronto Island Airport to Chicago. Users have found that Porter Airlines is 29% cheaper than the other options available to this destination.

COVID Restrictions

View COVID Travel Restrictions for Chicago, IL

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

Information is based on travel restrictions from Toronto Island to Chicago

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

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

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

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

Returning to Toronto Island from Chicago

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

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

Hide COVID Travel Restrictions for Chicago, IL

Alternative routes for Toronto Island to Chicago

See prices for flight routes from nearby airports that may be better suited for you.

Destination information for Chicago

Things to know before you go - useful duration and weather info for your trip from Toronto Island to Chicago.
Today's exchange rate
C$ 1 = $0.79
Flight duration from Toronto Island to Chicago
1h 43m
Average temperature for December in Chicago
3.0 °C
Avg rainfall for December in Chicago
31.0 mm

Airports servicing Toronto

Airports servicing Chicago

Midway (MDW)
Rockford (RFD)

Hourly flight availability from Toronto Island to Chicago

See what time of day planes typically take off from Toronto Island towards Chicago.
Afternoon Noon to 6 PM 61% of flight departures
Morning 6 AM to noon 38% of flight departures
Early morning Midnight to 6 AM 1% of flight departures
Evening 6 PM to midnight 0% of flight departures
Midnight
6 AM
Noon
6 PM
Weekly flight availability
from Toronto Island to Chicago
See how many times per day planes take to the skies headed from Toronto Island to Chicago.
Sunday
0 flights
Monday
3 daily flights
Tuesday
2 daily flights
Wednesday
2 daily flights
Thursday
3 daily flights
Friday
3 daily flights
Saturday
0 flights
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