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Cheap flights from Toronto (YTO) to Chicago (CHI) from $126

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 6/11. 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.
YTO — CHI
may. 21 — may. 281
From?
To?
mar. 5/21
mar. 5/28
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

The best prices from Toronto to Chicago are usually found in April or February, booked 37 days in advance, depart on a Wednesday or Thursday and return on a Saturday

Cheap flight deals from Toronto to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Toronto (YTO) 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 16, 2024.

Popular in

September

Cheapest in

April

Round-trip from

$223

One-way from

$150
High demand for flights, 13% potential price rise
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Best time to find cheap flights, 18% potential price drop
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From Toronto (YTO) to Chicago (CHI)
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One-way flight from Toronto (YTO) to Chicago (CHI)
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What is the cheapest day to fly round-trip from Toronto to Chicago?

It’s generally more expensive to depart on a Tuesday, if you have to leave on this day you can still search on Cheapflights to find great options that meet your needs.

How far in advance should I book a flight from Toronto 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 to Chicago from $344 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 to Chicago?

Our data shows that April tends to be the cheapest month to fly to Chicago from Toronto. Users have commonly found prices around $292 for the month, but tickets can be as low as $193. Due to multiple factors, prepare for potentially higher prices in September.

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

A simple way to save on the total cost of your ticket is to fly from Toronto to Chicago in the evening. If you’re flexible enough to do this you can expect to save up to 13% on your trip compared to booking a flight in the afternoon.

Cheap Air Canada flights from Toronto to Chicago

Explore cheap flight options specifically provided by Air Canada for the route between Toronto 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 2,637,452 searches. Data last updated mayo 16, 2024.
Consider these cheap Air Canada flights we've found departing from Toronto to Chicago. Come back soon if you're not finding the exact deal you're looking for.
dom. 7/147:00 amYYZ - ORD
Nonstop1h 56mAir Canada
mié. 7/176:00 amORD - YYZ
Nonstop1h 48mAir Canada
Deal found 5/14$242
sáb. 6/229:00 amYYZ - ORD
Nonstop1h 54mAir Canada
lun. 6/246:00 amORD - YYZ
Nonstop1h 48mAir Canada
Deal found 5/16$262
vie. 7/511:00 amYYZ - ORD
Nonstop2h 02mAir Canada
dom. 7/75:00 pmORD - YYZ
Nonstop1h 52mAir Canada
Deal found 5/16$267
lun. 6/179:00 pmYYZ - ORD
Nonstop2h 02mAir Canada
mié. 6/197:10 amORD - YYZ
Nonstop1h 48mAir Canada
Deal found 5/15$269
sáb. 6/2912:10 pmYYZ - ORD
1 stop7h 45mAir Canada
mié. 7/36:00 amORD - YYZ
Nonstop1h 48mAir Canada
Deal found 5/14$276
sáb. 5/252:00 pmYYZ - ORD
1 stop7h 16mAir Canada
mar. 5/289:15 pmORD - YYZ
Nonstop1h 43mAir Canada
Deal found 5/14$302
dom. 5/268:20 amYTZ - ORD
1 stop5h 53mAir Canada
mié. 9/182:00 pmORD - YTZ
1 stop5h 44mAir Canada
Deal found 5/16$330
vie. 5/2412:30 amYYZ - ORD
1 stop8h 28mAir Canada
mar. 5/289:15 pmORD - YYZ
Nonstop1h 43mAir Canada
Deal found 5/14$336
dom. 5/264:00 pmYYZ - ORD
1 stop5h 16mAir Canada
lun. 5/276:00 amORD - YYZ
Nonstop1h 45mAir Canada
Deal found 5/15$357

Cheap American Airlines flights from Toronto to Chicago

Explore cheap flight options specifically provided by American Airlines for the route between Toronto 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 2,637,452 searches. Data last updated mayo 16, 2024.
Have a look at some of the cheapest available American Airlines flights departing from Toronto and landing in Chicago. Make sure to examine the flight information before completing your reservation.
vie. 6/71:20 pmYYZ - ORD
Nonstop1h 55mAmerican Airlines
dom. 6/99:50 amORD - YYZ
Nonstop1h 50mAmerican Airlines
Deal found 5/16$243
sáb. 6/13:09 pmYYZ - ORD
Nonstop1h 55mAmerican Airlines
jue. 6/139:50 amORD - YYZ
Nonstop1h 50mAmerican Airlines
Deal found 5/16$251
sáb. 6/16:30 amYYZ - ORD
Nonstop1h 56mAmerican Airlines
jue. 6/135:07 amORD - YYZ
1 stop9h 17mAmerican Airlines
Deal found 5/15$260
vie. 5/316:30 amYYZ - ORD
Nonstop1h 56mAmerican Airlines
lun. 6/38:20 pmORD - YYZ
Nonstop1h 50mAmerican Airlines
Deal found 5/15$263
sáb. 6/297:23 pmYYZ - ORD
1 stop5h 35mAmerican Airlines
mié. 7/311:54 amORD - YYZ
Nonstop1h 35mAmerican Airlines
Deal found 5/16$264
mar. 6/411:55 amYYZ - ORD
Nonstop1h 55mAmerican Airlines
mar. 6/2511:54 amORD - YYZ
Nonstop1h 35mAmerican Airlines
Deal found 5/15$266
vie. 5/243:10 pmYYZ - ORD
Nonstop1h 55mAmerican Airlines
vie. 5/3111:54 amORD - YYZ
Nonstop1h 35mAmerican Airlines
Deal found 5/15$308
dom. 5/266:00 amYYZ - ORD
1 stop7h 40mAmerican Airlines
mié. 9/1811:45 amORD - YYZ
Nonstop1h 39mAmerican Airlines
Deal found 5/16$310
vie. 5/246:00 amYYZ - ORD
1 stop7h 40mAmerican Airlines
vie. 5/3111:54 amORD - YYZ
Nonstop1h 35mAmerican Airlines
Deal found 5/15$322

Cheap Toronto to Chicago flights in May & June 2024

Find cheap flight options from Toronto 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 2,637,452 searches. Prices were last updated on mayo 16, 2024.
These are some of the best deals we've found on flights to Chicago in 2024 at this time. Check back soon for alternative fares.
mar. 6/116:30 amYYZ - ORD
1 stop10h 58mMultiple Airlines
mar. 6/186:40 pmORD - YYZ
1 stop18h 20mMultiple Airlines
Deal found 5/15$216
mar. 6/189:20 amYTZ - MDW
Nonstop1h 47mPorter Airlines
lun. 6/248:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/14$217
jue. 6/138:50 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
sáb. 6/1512:30 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/15$221
mié. 6/269:20 amYTZ - MDW
Nonstop1h 47mPorter Airlines
mié. 7/318:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/15$222
mar. 6/46:30 amYYZ - ORD
1 stop12h 10mMultiple Airlines
mar. 6/116:40 pmORD - YYZ
1 stop18h 20mMultiple Airlines
Deal found 5/14$224
mar. 6/119:20 amYTZ - MDW
Nonstop1h 47mPorter Airlines
vie. 6/218:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/16$233
mié. 6/198:50 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
sáb. 6/2212:30 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/15$235
mar. 6/119:20 amYTZ - MDW
Nonstop1h 47mPorter Airlines
sáb. 6/2212:30 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/15$236
mié. 6/193:30 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
sáb. 6/2212:30 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/15$237

Toronto to Chicago 2024 flight deals

Discover exclusive flight deals for travel between Toronto and Chicago in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 2,637,452 searches. Data last updated mayo 16, 2024.
These are some of the best deals we've found on flights to Chicago in 2024 at this time. Check back soon for alternative fares.
mar. 6/116:30 amYYZ - ORD
1 stop10h 58mMultiple Airlines
mar. 6/186:40 pmORD - YYZ
1 stop18h 20mMultiple Airlines
Deal found 5/15$216
mar. 6/189:20 amYTZ - MDW
Nonstop1h 47mPorter Airlines
lun. 6/248:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/14$217
jue. 6/138:50 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
sáb. 6/1512:30 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/15$221
mié. 6/269:20 amYTZ - MDW
Nonstop1h 47mPorter Airlines
mié. 7/318:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/15$222
mar. 6/46:30 amYYZ - ORD
1 stop12h 10mMultiple Airlines
mar. 6/116:40 pmORD - YYZ
1 stop18h 20mMultiple Airlines
Deal found 5/14$224
sáb. 7/1310:45 amYTZ - MDW
Nonstop1h 47mPorter Airlines
mié. 7/1711:05 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/14$226
dom. 7/1410:30 amYTZ - MDW
Nonstop1h 47mPorter Airlines
mié. 7/1711:05 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/14$229
mar. 8/133:30 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
jue. 8/228:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/14$232
mar. 6/119:20 amYTZ - MDW
Nonstop1h 47mPorter Airlines
vie. 6/218:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/16$233

Non-stop flights to Chicago from Toronto

Discover non-stop flight options from Toronto 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 2,637,452 searches. Data last updated mayo 16, 2024.
Take a look at some of the direct flights traveling from Toronto to Chicago in the near future. If you're looking for other options for flights from Toronto to Chicago, make sure to update the search form at the top of page.
mié. 6/269:20 amYTZ - MDW
Nonstop1h 47mPorter Airlines
mié. 7/318:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/15$222
sáb. 7/1310:45 amYTZ - MDW
Nonstop1h 47mPorter Airlines
mié. 7/1711:05 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/14$226
dom. 7/1410:30 amYTZ - MDW
Nonstop1h 47mPorter Airlines
mié. 7/1711:05 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/14$229
mar. 8/133:30 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
jue. 8/228:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/14$232
mar. 6/119:20 amYTZ - MDW
Nonstop1h 47mPorter Airlines
vie. 6/218:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/16$233
mié. 6/198:50 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
sáb. 6/2212:30 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/15$235
mar. 6/119:20 amYTZ - MDW
Nonstop1h 47mPorter Airlines
sáb. 6/2212:30 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/15$236
mié. 6/193:30 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
sáb. 6/2212:30 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/15$237
mié. 7/108:50 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
mié. 7/1711:05 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/14$238

Toronto to Chicago flights leaving soon

Find last-minute flight options from Toronto 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 2,637,452 searches. Data last updated mayo 16, 2024.
Users seeking a last-minute flight from Toronto to Chicago should consider booking one of these fares. Tip: verify your flight details before completing your reservation.
sáb. 5/2510:45 amYTZ - MDW
Nonstop1h 47mPorter Airlines
mar. 5/288:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/14$286
sáb. 5/257:55 amYYZ - ORD
Nonstop1h 56mUnited Airlines
mar. 5/289:15 pmORD - YYZ
Nonstop1h 43mUnited Airlines
Deal found 5/14$297
sáb. 5/252:00 pmYYZ - ORD
1 stop7h 16mAir Canada
mar. 5/289:15 pmORD - YYZ
Nonstop1h 43mAir Canada
Deal found 5/14$302
vie. 5/243:10 pmYYZ - ORD
Nonstop1h 55mAmerican Airlines
vie. 5/3111:54 amORD - YYZ
Nonstop1h 35mAmerican Airlines
Deal found 5/15$308
dom. 5/266:00 amYYZ - ORD
1 stop7h 40mAmerican Airlines
mié. 9/1811:45 amORD - YYZ
Nonstop1h 39mAmerican Airlines
Deal found 5/16$310
dom. 5/263:30 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
mié. 9/188:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/16$311
dom. 5/2610:30 amYTZ - MDW
Nonstop1h 47mPorter Airlines
mar. 5/2811:05 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/16$316
sáb. 5/251:00 pmYYZ - ORD
Nonstop2h 02mUnited Airlines
mar. 5/289:15 pmORD - YYZ
Nonstop1h 43mUnited Airlines
Deal found 5/14$317
sáb. 5/256:15 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
mar. 5/288:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/15$317

One-way flights to Chicago from Toronto

Search for one-way flight options from Toronto 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 2,637,452 searches. Data last updated mayo 16, 2024.
If you're seeking multiple options on one-way flights from Toronto to Chicago, be sure to check out these deals, which are updated often. Those seeking round-trip flights from Toronto to Chicago should utilize the search form at the the top of the page.
mar. 6/116:30 amYYZ - ORD
1 stop16h 28mMultiple Airlines
Deal found 5/14$126
lun. 6/249:20 amYTZ - MDW
Nonstop1h 47mPorter Airlines
Deal found 5/15$129
mié. 6/56:30 amYYZ - ORD
1 stop10h 58mMultiple Airlines
Deal found 5/16$131
mar. 6/47:45 amYYZ - ORD
1 stop15h 01mMultiple Airlines
Deal found 5/15$132
lun. 6/36:30 amYYZ - ORD
1 stop28h 25mMultiple Airlines
Deal found 5/16$133
lun. 7/13:30 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
Deal found 5/14$133
mié. 6/128:50 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
Deal found 5/14$135
dom. 7/2110:30 amYTZ - MDW
Nonstop1h 47mPorter Airlines
Deal found 5/15$136
vie. 6/78:50 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
Deal found 5/15$137

Find flights from Toronto to Chicago within your budget

Customize your flight search to find flights from Toronto 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 2,637,452 searches. Data last updated mayo 16, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$216 - $305

Route

Depart

Return

Price

Toronto Pearson IntlChicago O'Hare Intl

YYZ - ORD

YYZORD

Toronto Pearson Intl

mar. 6/11

1 stop10h 58m

Chicago O'Hare Intl

mar. 6/18

1 stop18h 20m

$216

Toronto IslandChicago Midway

YTZ - MDW

YTZMDW

Toronto Island

mar. 6/18

Nonstop1h 47m

Chicago Midway

lun. 6/24

Nonstop1h 42m

$217

Toronto IslandChicago Midway

YTZ - MDW

YTZMDW

Toronto Island

jue. 6/13

Nonstop1h 47m

Chicago Midway

sáb. 6/15

Nonstop1h 42m

$221

Toronto Pearson IntlChicago O'Hare Intl

YYZ - ORD

YYZORD

Toronto Pearson Intl

dom. 7/14

Nonstop1h 56m

Chicago O'Hare Intl

mié. 7/17

Nonstop1h 48m

$242

Toronto Pearson IntlChicago O'Hare Intl

YYZ - ORD

YYZORD

Toronto Pearson Intl

vie. 6/7

Nonstop1h 55m

Chicago O'Hare Intl

dom. 6/9

Nonstop1h 50m

$243

Toronto Pearson IntlChicago O'Hare Intl

YYZ - ORD

YYZORD

Toronto Pearson Intl

dom. 6/16

Nonstop1h 57m

Chicago O'Hare Intl

mar. 6/18

1 stop9h 13m

$268

Toronto Pearson IntlChicago O'Hare Intl

YYZ - ORD

YYZORD

Toronto Pearson Intl

mar. 7/16

1 stop6h 54m

Chicago O'Hare Intl

jue. 7/18

1 stop7h 08m

$272

Toronto Pearson IntlChicago O'Hare Intl

YYZ - ORD

YYZORD

Toronto Pearson Intl

vie. 9/6

1 stop5h 05m

Chicago O'Hare Intl

dom. 9/8

1 stop3h 55m

$302

Toronto Pearson IntlChicago Midway

YYZ - MDW

YYZMDW

Toronto Pearson Intl

lun. 6/17

1 stop8h 19m

Chicago Midway

mié. 6/19

1 stop6h 34m

$305

Flights are sorted by cheapest first

Deals found on 5/15

When is the best time to book a flight from Toronto to Chicago?

Use this chart to determine the optimal time to book a round-trip flight from Toronto to Chicago. Price data was last updated on May 10, 2024.
To ensure you get the cheapest price possible for a flight from Toronto to Chicago, you should look to book at least 37 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
Search Deals

When is the cheapest time to fly from Toronto to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Toronto to Chicago. Price data was last updated on May 12, 2024.
Morning
Noon
Afternoon
Evening
All times are departure.
Travelers seeking maximum savings on their Toronto to Chicago flight should consider departing on Monday at noon when fares are most often at their lowest. Sunday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
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Average price of flights to Chicago by month

Plan your trip from Toronto to Chicago by taking into account the cheapest months to travel. The average price of a one-way flight from Toronto to Chicago is currently $132 while a round-trip flight costs $254. Price data was last updated on May 12, 2024.

Currently, February is the cheapest month in which you can book a flight from Toronto to Chicago (average of $244). Flying from Toronto to Chicago in June is currently the most expensive (average of $342). 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.

January

$248

February

$244

March

$280

April

$258

May

$278

June

$342

July

$327

August

$274

September

$258

October

$248

November

$270

December

$248

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 16, 2024.
Read through reviews of airlines operating flights from Toronto to Chicago, such as Air Canada, American Airlines and United Airlines. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
10,673 reviews
Check prices

Crew

8.6

Boarding

8.2

Overall

8.0

Food

7.4

Comfort

7.9

Entertainment

8.0

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

Delta
8.0
Very good
10,673 reviews
Delta
8.0
Very good
10,673 reviews
Check prices

Crew

8.6

Boarding

8.2

Overall

8.0

Food

7.4

Comfort

7.9

Entertainment

8.0

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

KLM
7.9
Good
1,568 reviews
Delta
8.0
Very good
10,673 reviews
Check prices

Crew

8.6

Boarding

8.2

Overall

8.0

Food

7.4

Comfort

7.9

Entertainment

8.0

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

Aeromexico
7.6
Good
2,528 reviews
Delta
8.0
Very good
10,673 reviews
Check prices

Crew

8.6

Boarding

8.2

Overall

8.0

Food

7.4

Comfort

7.9

Entertainment

8.0

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

WestJet
7.5
Good
2,919 reviews
Delta
8.0
Very good
10,673 reviews
Check prices

Crew

8.6

Boarding

8.2

Overall

8.0

Food

7.4

Comfort

7.9

Entertainment

8.0

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

Porter Airlines
7.4
Good
415 reviews
Delta
8.0
Very good
10,673 reviews
Check prices

Crew

8.6

Boarding

8.2

Overall

8.0

Food

7.4

Comfort

7.9

Entertainment

8.0

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

Related info for your journey

Find useful and relevant information for your journey from Toronto 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 to Chicago for under $300 on Cheapflights?

    Yes, there are multiple flights from Toronto to Chicago for under $300. The cheapest flight booked recently is on Multiple Airlines for just $216, but on average you can expect to pay $233.

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

    Cheapflights has at least 20 direct flights from Toronto to Chicago under $300. A good price for a nonstop flight from Toronto to Chicago is less than $240.

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

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

  • What days are nonstop flights available from Toronto to Chicago?

    Days when nonstop flights are available for this flight are: Sunday, Monday, Tuesday, Thursday, Friday, Saturday.

  • How many flights depart from Toronto to Chicago on average per day?

    29 flight departures from Toronto to Chicago per day on average.
    Morning (6am - Noon) - 24% of flight departures
    Afternoon (Noon - 6pm) - 66% of flight departures
    Evening (6pm - Midnight) - 10% of flight departures

  • How long is the flight from Toronto to Chicago?

    Porter Airlines, Air Canada, and American Airlines can get you from Toronto to Chicago in just under 1h 47m. Your travel time will be generally consistent. There are 437 mi between Toronto and Chicago. Generally, flights for this route are nonstop.

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

    Our cheapest airline available from Toronto to Chicago is Porter Airlines. Our recent data shows that you can find tickets from as low as $217 on this airline. Additional options worth looking into are Air Canada and American Airlines, starting at $242 and $243 round-trip. Porter Airlines is currently priced 25% below the average price you’ll pay for this route.

  • What are the most popular routes from Toronto to Chicago?

    The most popular flight routes from Toronto to Chicago are Toronto Pearson Intl - Chicago O'Hare Intl, Toronto Island - Chicago Midway and Toronto Pearson Intl - Chicago Midway.

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

    Consider American Airlines, Air Canada or Porter Airlines when booking your flight. These represent the most popular airlines when flying from Toronto to Chicago.

  • What are the most reliable airlines from Toronto to Chicago?

    Consider Republic Airways (94%), Copa Airlines (93%) or SkyWest Airlines (92%) when booking your flight. These represent the most reliable airlines when flying from Toronto to Chicago.

  • What are the cheapest flights from Toronto to Chicago?

    Looking for the cheapest flight from Toronto to Chicago? While on average our users pay $1,627, our data indicates the cheapest price to be $151. The most popular route (Toronto Pearson Intl - Chicago O'Hare Intl), is priced around $242.

  • What does YYZ to ORD mean?

    Great question - YYZ to ORD just means Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport. Now you’ll know what these unique codes when you look for flights! While you’re still figuring out your travel plans, it’s not a bad idea to learn the names and codes of other airports around these areas: Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD).

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

    The amount of baggage you can bring on your Toronto 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 to Chicago with specific airlines?

    Yes, Cheapflights allows you to browse and filter Toronto 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 to Chicago that include hotel bookings?

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

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

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

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

    Yes. Cheapflights offers flight deals from Toronto 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 to Chicago that allow pets onboard?

    Many airlines flying from Toronto 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 to Chicago?

    Yes, you can often find last-minute deals on Toronto 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 to Chicago flight deals updated?

    The Toronto to Chicago flight deals you see on this page were last updated on 5/16.

See more FAQs

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

Pearson Intl to O'Hare Intl flights
Pierre Elliott Trudeau Intl to O'Hare Intl flights
Toronto Island to Midway flights
Pierre Elliott Trudeau Intl to Midway flights
Pearson Intl to Midway flights
Toronto Island to O'Hare Intl flights
Ottawa to Midway flights
Pearson Intl to St. Louis flights
Ottawa to O'Hare Intl flights
Pierre Elliott Trudeau Intl to St. Louis flights
Hamilton to O'Hare Intl flights
London to O'Hare Intl flights
Ottawa to St. Louis flights
Ottawa to Bloomington flights
Pearson Intl to Peoria flights
London to Midway flights

Top 4 airlines flying from Toronto to Chicago

Discover the top 4 airlines that operate flights from Toronto 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 2,637,452 searches. Data last updated mayo 16, 2024.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$206Average$286FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
Air CanadaCheapest$214Average$361FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
United AirlinesCheapest$232Average$352FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
American AirlinesCheapest$248Average$390FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
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Search flights from Toronto to Chicago by cabin class

Find flights from Toronto to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
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Hourly flight availability from Toronto to Chicago

Find hourly flight availability from Toronto 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 16, 2024.
11%of flight departuresEarly morningMidnight to 6 am
26%of flight departuresMorning6 am to noon
50%of flight departuresAfternoonNoon to 6 pm
13%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM

Weekly flight availability from Toronto to Chicago

Explore weekly flight availability from Toronto 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 16, 2024.
Sunday54daily flights
Monday57daily flights
Tuesday51daily flights
Wednesday48daily flights
Thursday57daily flights
Friday66daily flights
Saturday46daily flights

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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 to Chicago?

Cheapflights helps you search for flights from Toronto to Chicago via 900+ travel sites so you don’t have to. After performing a flight search, users can also filter their flight selection by filtering for price, number of stops, airlines, and so on.

Why should you use Cheapflights to find cheap flight tickets from Toronto 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.

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

Certainly. Search results for flights to Chicago from Toronto 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 to Chicago become cheaper?

Yes! Start tracking prices for Toronto to Chicago flights today and get alerted whenever prices for these flights change. To access this feature, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive your alerts.

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