HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news

Cheap flights from Toronto Island (YTZ) to Chicago (CHI) from $124

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/5. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
YTZ — CHI
jun. 4 — jun. 111
From?
To?
mar. 6/4
mar. 6/11
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Cheap flight deals from Toronto Island to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Toronto Island (YTZ) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated mayo 30, 2024.

Popular in

July

Cheapest in

December

Round-trip from

$222

One-way from

$160
High demand for flights, 21% potential price rise
Search Deals
Best time to find cheap flights, 18% potential price drop
Search Deals
From Toronto Island to Chicago (CHI)
Search Deals
One-way flight from Toronto Island to Chicago (CHI)
Search Deals

What is the cheapest day to fly round-trip from Toronto Island Airport to Chicago?

Flying to your destination on a Saturday can be more expensive, but this shouldn’t discourage you from finding affordable options to get to Chicago. Check prices with Cheapflights to find a great deal for your trip.

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

To save up to 90% on this flight, we recommend booking at least 38 days prior to travel. The price may fluctuate and will likely increase closer to your departure date. Users on Cheapflights have found tickets from Toronto Island Airport to Chicago from $337 1-2 weeks out and tickets from $489 for flights departing within the next 72 hours.

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

April is one of the best times of the year to fly to Chicago from Toronto Island Airport. Prices for April average $291 per person but you can even find prices for as low as $193. The most expensive prices can be found in the month of September. Opting for a April flight can save you 14% on your journey compared to booking in September

What is the cheapest time of day to fly from YTZ to CHI?

Unlike in the morning, when flights are generally more expensive, you can save up to 21% on flights from Toronto Island Airport to Chicago by exploring options for tickets in the evening.

Cheap Air Canada flights from Toronto Island to Chicago

Explore cheap flight options specifically provided by Air Canada for the route between Toronto Island and Chicago. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,784,634 searches. Data last updated mayo 30, 2024.
Peruse some of the lowest-priced Air Canada flights we've found from Toronto to Chicago. Be sure to come back soon if the deals available don't appeal to you at this time.
mar. 6/188:20 amYTZ - ORD
1 stop5h 53mAir Canada
mar. 6/251:55 pmORD - YTZ
1 stop4h 54mAir Canada
Deal found 5/29$249
mar. 7/28:20 amYTZ - ORD
1 stop5h 53mAir Canada
jue. 7/41:55 pmORD - YTZ
1 stop5h 49mAir Canada
Deal found 5/30$261
vie. 6/148:20 amYTZ - ORD
1 stop5h 53mAir Canada
mar. 6/181:55 pmORD - YTZ
1 stop5h 49mAir Canada
Deal found 5/29$262
jue. 10/109:20 amYTZ - ORD
1 stop4h 17mAir Canada
dom. 10/132:00 pmORD - YTZ
1 stop5h 44mAir Canada
Deal found 5/29$270
mié. 6/128:20 amYTZ - ORD
1 stop5h 53mAir Canada
mié. 6/191:55 pmORD - YTZ
1 stop5h 49mAir Canada
Deal found 5/29$285
mar. 7/3010:20 amYTZ - ORD
1 stop5h 20mAir Canada
jue. 8/11:55 pmORD - YTZ
1 stop5h 49mAir Canada
Deal found 5/29$290
vie. 7/1910:20 amYTZ - ORD
1 stop5h 20mAir Canada
dom. 7/218:45 amORD - YTZ
1 stop5h 04mAir Canada
Deal found 5/29$291
mié. 10/98:20 amYTZ - ORD
1 stop5h 48mAir Canada
dom. 10/132:00 pmORD - YTZ
1 stop5h 44mAir Canada
Deal found 5/29$292
mar. 6/1812:20 pmYTZ - ORD
1 stop7h 13mAir Canada
vie. 6/211:55 pmORD - YTZ
1 stop5h 49mAir Canada
Deal found 5/28$296

Cheap Porter Airlines flights from Toronto Island to Chicago

Explore cheap flight options specifically provided by Porter Airlines for the route between Toronto Island and Chicago. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,784,634 searches. Data last updated mayo 30, 2024.
Some of the best deals we've found on Porter Airlines flights traveling from Toronto to Chicago. Ensure the flight price, dates, time, and airline match your criteria before you book.
lun. 7/299:20 amYTZ - MDW
Nonstop1h 47mPorter Airlines
sáb. 8/312:30 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/29$210
jue. 6/273:30 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
jue. 7/411:30 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/30$217
vie. 6/143:30 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
mar. 6/188:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/29$218
jue. 7/253:30 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
lun. 7/295:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/28$221
jue. 6/138:50 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
dom. 6/308:40 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/28$222
lun. 7/19:20 amYTZ - MDW
Nonstop1h 47mPorter Airlines
jue. 7/48:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/28$223
mar. 6/189:20 amYTZ - MDW
Nonstop1h 47mPorter Airlines
vie. 7/58:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/29$224
vie. 6/143:30 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
lun. 6/175:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/29$225
jue. 6/133:30 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
sáb. 6/1512:30 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/29$226

Cheap Toronto Island to Chicago flights in May & June 2024

Find cheap flight options from Toronto Island to Chicago specifically for the months of May and June 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,784,634 searches. Prices were last updated on mayo 30, 2024.
The lowest fares we've come across on flights traveling from Toronto to Chicago in May and June 2024. If these deals don't appeal to you, be sure to come back soon for more options.
sáb. 6/296:15 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
sáb. 7/68:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/30$222
mié. 6/199:20 amYTZ - MDW
Nonstop1h 47mPorter Airlines
mié. 6/195:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/30$223
mar. 6/189:20 amYTZ - MDW
Nonstop1h 47mPorter Airlines
vie. 7/58:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/29$224
vie. 6/143:30 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
lun. 6/175:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/29$225
jue. 6/133:30 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
sáb. 6/1512:30 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/29$226
vie. 6/143:30 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
jue. 6/205:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/29$229
mar. 6/258:50 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
sáb. 6/298:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/28$235
jue. 6/133:30 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
lun. 6/175:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/30$236
vie. 6/148:50 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
sáb. 6/1512:30 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/29$237

Toronto Island to Chicago 2024 flight deals

Discover exclusive flight deals for travel between Toronto Island and Chicago in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 2,784,634 searches. Data last updated mayo 30, 2024.
The lowest fares we've come across on flights traveling from Toronto to Chicago in May and June 2024. If these deals don't appeal to you, be sure to come back soon for more options.
sáb. 6/296:15 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
sáb. 7/68:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/30$222
mié. 6/199:20 amYTZ - MDW
Nonstop1h 47mPorter Airlines
mié. 6/195:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/30$223
vie. 7/193:30 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
dom. 7/218:40 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/29$224
vie. 6/143:30 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
lun. 6/175:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/29$225
jue. 6/133:30 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
sáb. 6/1512:30 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/29$226
lun. 7/19:20 amYTZ - MDW
Nonstop1h 47mPorter Airlines
mié. 7/35:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/29$227
mié. 7/249:20 amYTZ - MDW
Nonstop1h 47mPorter Airlines
dom. 7/288:40 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/28$229
dom. 7/288:50 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
mié. 8/75:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/29$230
jue. 10/33:30 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
dom. 10/612:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/30$231

Non-stop flights to Chicago from Toronto Island

Discover non-stop flight options from Toronto Island to Chicago. Find direct flights with no layovers, providing a convenient travel experience. Explore non-stop flight options based on user searches, and compare prices and availability for your desired travel dates. Over the last 7 days, Cheapflights users made 2,784,634 searches. Data last updated mayo 30, 2024.
Take a look at some of the direct flights traveling from Toronto to Chicago in the near future. Search for alternative flights from Toronto to Chicago by utilizing the search form above.
sáb. 6/296:15 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
sáb. 7/68:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/30$222
mié. 6/199:20 amYTZ - MDW
Nonstop1h 47mPorter Airlines
mié. 6/195:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/30$223
vie. 7/193:30 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
dom. 7/218:40 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/29$224
vie. 6/143:30 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
lun. 6/175:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/29$225
jue. 6/133:30 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
sáb. 6/1512:30 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/29$226
lun. 7/19:20 amYTZ - MDW
Nonstop1h 47mPorter Airlines
mié. 7/35:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/29$227
mié. 7/249:20 amYTZ - MDW
Nonstop1h 47mPorter Airlines
dom. 7/288:40 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/28$229
dom. 7/288:50 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
mié. 8/75:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/29$230
mié. 7/318:50 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
jue. 8/811:30 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/29$232

Toronto Island to Chicago flights leaving soon

Find last-minute flight options from Toronto Island to Chicago for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 2,784,634 searches. Data last updated mayo 30, 2024.
Users seeking a last-minute flight from Toronto to Chicago should consider booking one of these fares. Users should examine the flight details to ensure there are no surprises.
jue. 6/138:50 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
dom. 6/308:40 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/28$222
mié. 6/128:50 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
sáb. 6/158:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/29$224
jue. 6/133:30 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
sáb. 6/1512:30 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/29$226
jue. 6/133:30 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
sáb. 6/158:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/28$235
mié. 6/129:20 amYTZ - MDW
Nonstop1h 47mPorter Airlines
mié. 6/195:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/29$237
jue. 6/133:30 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
lun. 6/175:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/29$249
lun. 6/109:20 amYTZ - MDW
Nonstop1h 47mPorter Airlines
sáb. 6/1512:30 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/28$267
lun. 6/108:50 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
jue. 6/205:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/29$275
lun. 6/108:50 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
lun. 7/158:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/29$276

One-way flights to Chicago from Toronto Island

Search for one-way flight options from Toronto Island to Chicago. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 2,784,634 searches. Data last updated mayo 30, 2024.
Users traveling one-way from Toronto to Chicago can select one of these great deals. Those needing a return flight from Toronto to Chicago can use the search form above.
lun. 8/53:30 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
Deal found 5/29$124
dom. 7/288:50 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
Deal found 5/29$126
mié. 7/313:30 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
Deal found 5/29$128
jue. 8/158:50 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
Deal found 5/29$129
lun. 7/18:50 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
Deal found 5/28$130
mié. 6/193:30 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
Deal found 5/29$133
jue. 6/133:30 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
Deal found 5/29$135
vie. 6/148:50 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
Deal found 5/29$136
mar. 7/98:50 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
Deal found 5/28$137

Find flights from Toronto Island to Chicago within your budget

Customize your flight search to find flights from Toronto Island to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,784,634 searches. Data last updated mayo 30, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$210 - $288

Route

Depart

Return

Price

Toronto IslandChicago Midway

YTZ - MDW

YTZMDW

Toronto Island

lun. 7/29

Nonstop1h 47m

Chicago Midway

sáb. 8/3

Nonstop1h 42m

$210

Toronto IslandChicago Midway

YTZ - MDW

YTZMDW

Toronto Island

jue. 6/27

Nonstop1h 47m

Chicago Midway

jue. 7/4

Nonstop1h 42m

$217

Toronto IslandChicago Midway

YTZ - MDW

YTZMDW

Toronto Island

vie. 6/14

Nonstop1h 47m

Chicago Midway

mar. 6/18

Nonstop1h 42m

$218

Toronto IslandChicago Midway

YTZ - MDW

YTZMDW

Toronto Island

jue. 7/25

Nonstop1h 47m

Chicago Midway

lun. 7/29

Nonstop1h 42m

$221

Toronto IslandChicago O'Hare Intl

YTZ - ORD

YTZORD

Toronto Island

mar. 6/18

1 stop5h 53m

Chicago O'Hare Intl

mar. 6/25

1 stop4h 54m

$249

Toronto IslandChicago O'Hare Intl

YTZ - ORD

YTZORD

Toronto Island

mar. 7/2

1 stop5h 53m

Chicago O'Hare Intl

jue. 7/4

1 stop5h 49m

$261

Toronto IslandChicago O'Hare Intl

YTZ - ORD

YTZORD

Toronto Island

vie. 6/14

1 stop5h 53m

Chicago O'Hare Intl

mar. 6/18

1 stop5h 49m

$262

Toronto IslandChicago O'Hare Intl

YTZ - ORD

YTZORD

Toronto Island

lun. 6/10

3 stops31h 00m

Chicago O'Hare Intl

jue. 6/13

2 stops16h 09m

$286

Toronto IslandChicago O'Hare Intl

YTZ - ORD

YTZORD

Toronto Island

mar. 6/18

1 stop12h 52m

Chicago O'Hare Intl

mié. 6/26

1 stop8h 51m

$288

Flights are sorted by cheapest first

Deals found on 5/29

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

Use this chart to determine the cheapest time to fly round-trip from Toronto Island to Chicago. Price data was last updated on May 26, 2024.
Morning
Noon
Afternoon
Evening
All times are departure.
Travelers seeking maximum savings on their Toronto Island Airport to Chicago flight should consider departing on Wednesday mornings when fares are most often at their lowest. Thursday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
Search Deals

Best time to book a flight from Toronto Island to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Toronto Island with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Temperature and rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average temperature and rainfall totals by month.

CHI

Temperature

23 - 73.4 °F

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated mayo 30, 2024.
Read reviews from past customers who have flown Air Canada and Porter Airlines from Toronto to Chicago. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
7.4
Good
394 reviews
Check prices

Boarding

7.6

Crew

8.2

Food

7.4

Comfort

7.5

Entertainment

6.6

Overall

7.4

Reviews

1 / 10

Uneventful but one attendant kept telling me to stow my backpack throughout the flight

Porter Airlines
7.4
Good
394 reviews
Porter Airlines
7.4
Good
394 reviews
Check prices

Boarding

7.6

Crew

8.2

Food

7.4

Comfort

7.5

Entertainment

6.6

Overall

7.4

Reviews

1 / 10

Uneventful but one attendant kept telling me to stow my backpack throughout the flight

Air Canada
7.0
Good
7,004 reviews
Porter Airlines
7.4
Good
394 reviews
Check prices

Boarding

7.6

Crew

8.2

Food

7.4

Comfort

7.5

Entertainment

6.6

Overall

7.4

Reviews

1 / 10

Uneventful but one attendant kept telling me to stow my backpack throughout the flight

Related info for your journey

Find useful and relevant information for your journey from Toronto Island to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

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

    Yes, there are multiple flights from Toronto Island Airport to Chicago for under $300. The cheapest flight booked recently is on Porter Airlines for just $210, but on average you can expect to pay $227.

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

    Cheapflights has at least 20 direct flights from Toronto Island Airport to Chicago under $300. A good price for a nonstop flight from Toronto Island Airport to Chicago is less than $233.

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

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

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

    According to our current data, Porter Airlines ($210), and Air Canada ($249) offers the cheapest pricing from Toronto Island Airport to Chicago. Porter Airlines is currently priced 29% below the average price you’ll pay for this route.

  • What does YTZ to ORD mean?

    Great question - YTZ to ORD just means Toronto Island Airport to Chicago O'Hare Intl Airport. Now you’ll know what these unique codes when you look for flights! Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD) are other airports near this flight route and their unique identifiers/IATA codes.

  • Can I find deals for flights from Toronto Island to Chicago that include extra baggage allowance?

    The amount of baggage you can bring on your Toronto Island to Chicago flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Toronto Island to Chicago with specific airlines?

    Yes, Cheapflights allows you to browse and filter Toronto Island to Chicago flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • Can I find deals for flights from Toronto Island to Chicago that include hotel bookings?

    Yes. In addition to deals on Toronto Island to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Toronto Island to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Toronto Island to Chicago.

  • Can I find deals for business class flights from Toronto Island to Chicago?

    Yes. Cheapflights offers flight deals from Toronto Island to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • Can I find deals for flights from Toronto Island to Chicago that allow pets onboard?

    Many airlines flying from Toronto Island to Chicago offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Toronto Island to Chicago?

    Yes, you can often find last-minute deals on Toronto Island to Chicago flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Toronto Island Airport to Chicago flight deals updated?

    The Toronto Island Airport to Chicago flight deals you see on this page were last updated on 5/30.

  • What is the cheapest month to book a flight from Toronto Island Airport to Chicago?

    Currently, February is the cheapest month in which you can book a flight from Toronto Island Airport to Chicago (average of $244). Flying from Toronto Island Airport to Chicago in June is currently the most expensive (average of $326). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Toronto Island to Chicago
See prices for flight routes from nearby airports that may be better suited for you.

Pearson Intl to O'Hare Intl flights
Toronto Island to Midway flights
Pearson Intl to Midway flights
Toronto Island to O'Hare Intl flights
Pearson Intl to St. Louis flights
Hamilton to O'Hare Intl flights
Pearson Intl to Peoria flights

Top 2 airlines flying from Toronto Island to Chicago

Discover the top 2 airlines that operate flights from Toronto Island to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,784,634 searches. Data last updated mayo 30, 2024.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$206Average$291FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
Air CanadaCheapest$241Average$404FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
Tampa to New York flights
Detroit to New York flights
USA to Bermuda flights
Cincinnati to Denver flights
New Orleans to New York flights
USA to Switzerland flights
Atlanta to Houston flights
New York to Niagara Falls, New York flights
Las Vegas to Houston flights
Chicago to Phoenix flights
Chicago to Cancún flights
Toronto Island Airport to Charlotte flights

Search flights from Toronto Island to Chicago by cabin class

Find flights from Toronto Island to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
First Class
Business Class
Prem Econ Class
Economy Class

Hourly flight availability from Toronto Island to Chicago

Find hourly flight availability from Toronto Island to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated mayo 30, 2024.
0%of flight departuresEarly morningMidnight to 6 am
35%of flight departuresMorning6 am to noon
35%of flight departuresAfternoonNoon to 6 pm
30%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM

Weekly flight availability from Toronto Island to Chicago

Explore weekly flight availability from Toronto Island to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated mayo 30, 2024.
Sunday1daily flight
Monday2daily flights
Tuesday2daily flights
Wednesday2daily flights
Thursday3daily flights
Friday3daily flights
Saturday1daily flight

Book a flight to one of these trending destinations

User searches for flights to these destinations increased 20% or more in the past 90 days compared to other destinations
Flights to Laayoune Hassan I
Flights to Virac
Flights to Figari-Sud Corse
Flights to Edremit/Korfez
Flights to Rhinelander Oneida County
Flights to Girona Costa Brava
Flights to Brainerd Crow Wing County
Flights to Parikia Paros
Flights to Cortez Montezuma County
Flights to Miyakojima Hirara
Flights to Zadar
Flights to Trapani Birgi
Flights to Provincetown
Flights to Oran Es Senia
Flights to Constanţa Mihail Kogalniceanu
Flights to Vava'u Lupepau'U
Flights to Urumqi
Flights to Hakodate
Flights to Naxos
Flights to Dalaman
Flights to Hyannis Barnstable
Flights to Devils Lake
Flights to Bastia Poretta
Flights to Karpathos

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Toronto Island to Chicago?

Deals for Toronto Island to Chicago flights are sourced from 900+ travel sites when you use Cheapflights. When all flight results come back, Cheapflights lets you sort and filter flights using different criteria to choose better, like price, airport, cabin class, and plenty of other options.

Why should you use Cheapflights to find cheap flight tickets from Toronto Island to Chicago?

By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Chicago from Toronto Island.

Can Cheapflights find flights from Toronto Island to Chicago with no change fees?

Certainly. Search results for flights to Chicago from Toronto Island shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

Can Cheapflights notify me if prices for flights from Toronto Island to Chicago become cheaper?

Not ready to book yet? You can track prices for flights from Toronto Island to Chicago on Cheapflights with our Price Alert feature and get notified when better prices are available.

100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.
View all available airlines