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Cheap flights from Toronto to Chicago from C$ 164

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 17/4. 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
24 Mar — 31 Mar1
1 adult
Sun 24/3
Sun 31/3

The best prices from Toronto to Chicago are usually found in January or February, booked 78 days in advance, depart on a Saturday or Wednesday and return on a Wednesday

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 19 March 2024.

Popular in

July

Cheapest in

January

Round-trip from

C$ 355

One-way from

C$ 165
High demand for flights, 14% potential price rise
Best time to find cheap flights, 21% potential price drop
From Toronto (YTO) to Chicago (CHI)
One-way flight from Toronto (YTO) to Chicago (CHI)

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

Friday is generally a great day to depart. Flying on this day could help you save up to 9%.

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

Find a great deal and save up to 78% by booking at least 27 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$ 486.

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

January is one of the best times of the year to fly to Chicago from Toronto. Prices for January average C$ 395 per person but you can even find prices for as low as C$ 241. The most expensive prices can be found in the month of July. Opting for a January flight can save you 16% on your journey compared to booking in July

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

Unlike in the afternoon, when flights are generally more expensive, you can save up to 7% on flights from Toronto to Chicago by exploring options for tickets in the evening.

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 525,491 searches. Data last updated 19 March 2024.
Take a look at some of the lowest-priced American Airlines flights heading from Toronto to Chicago. It's recommended that users confirm their flight details before booking.
Wed 10/411:55 a.m.YYZ - ORD
Nonstop1h 55mAmerican Airlines
Wed 17/48:30 a.m.ORD - YYZ
Nonstop1h 45mAmerican Airlines
Deal found 17/3C$ 317
Wed 10/46:30 a.m.YYZ - ORD
Nonstop1h 55mAmerican Airlines
Wed 17/46:35 a.m.ORD - YYZ
1 stop8h 02mAmerican Airlines
Deal found 17/3C$ 328
Sat 6/41:15 p.m.YYZ - ORD
Nonstop1h 55mAmerican Airlines
Tue 9/49:55 a.m.ORD - YYZ
Nonstop1h 40mAmerican Airlines
Deal found 17/3C$ 333
Sat 6/411:55 a.m.YYZ - ORD
Nonstop1h 55mAmerican Airlines
Tue 9/45:30 a.m.ORD - YYZ
1 stop9h 07mAmerican Airlines
Deal found 17/3C$ 344
Sat 6/411:55 a.m.YYZ - ORD
Nonstop1h 55mAmerican Airlines
Sun 7/46:36 a.m.ORD - YYZ
1 stop4h 19mAmerican Airlines
Deal found 17/3C$ 345
Wed 17/46:30 a.m.YYZ - ORD
Nonstop1h 55mAmerican Airlines
Wed 24/48:05 a.m.ORD - YYZ
1 stop6h 32mAmerican Airlines
Deal found 18/3C$ 352
Thu 28/37:14 a.m.YYZ - ORD
1 stop7h 16mAmerican Airlines
Mon 1/46:03 a.m.ORD - YYZ
1 stop5h 17mAmerican Airlines
Deal found 18/3C$ 448
Thu 28/37:14 a.m.YYZ - ORD
1 stop6h 26mAmerican Airlines
Mon 1/48:45 a.m.ORD - YYZ
1 stop5h 19mAmerican Airlines
Deal found 18/3C$ 449
Thu 28/37:14 a.m.YYZ - ORD
1 stop6h 26mAmerican Airlines
Mon 1/46:03 a.m.ORD - YYZ
1 stop8h 19mAmerican Airlines
Deal found 18/3C$ 462
  • If you’re travelling from Toronto to Chicago, one of the more common airlines travelling that route is American Airlines. Flights from American Airlines travelling this route typically cost C$ 321.64 RT. This price is typically 98% cheaper than other airlines that offer Toronto to Chicago flights. When booking this route, the cheapest RT price found was C$ 237. Toronto Pearson Intl Airport is the most common Toronto airport to take off from when flying to Chicago. Chicago O'Hare Intl Airport is the most popular arrival airport in Chicago. When flying from Toronto to Chicago, American Airlines flights are 6% more popular than any other airline flying that same route.

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 525,491 searches. Data last updated 19 March 2024.
Browse through some of the cheapest Air Canada flights travelling from Toronto to Chicago. Deals frequently update to provide users with more options.
Thu 11/48:00 a.m.YYZ - ORD
Nonstop1h 54mAir Canada
Mon 15/49:15 p.m.ORD - YYZ
Nonstop1h 43mAir Canada
Deal found 17/3C$ 318
Wed 24/48:00 a.m.YYZ - ORD
Nonstop1h 54mAir Canada
Mon 27/59:15 p.m.ORD - YYZ
Nonstop1h 43mAir Canada
Deal found 18/3C$ 322
Sat 20/44:00 p.m.YYZ - ORD
1 stop5h 06mAir Canada
Wed 24/49:15 p.m.ORD - YYZ
Nonstop1h 43mAir Canada
Deal found 16/3C$ 325
Sun 26/59:00 a.m.YYZ - ORD
Nonstop1h 54mAir Canada
Mon 27/59:15 p.m.ORD - YYZ
Nonstop1h 43mAir Canada
Deal found 17/3C$ 326
Sat 6/412:30 p.m.YYZ - ORD
Nonstop1h 54mAir Canada
Sun 7/49:15 p.m.ORD - YYZ
Nonstop1h 43mAir Canada
Deal found 17/3C$ 334
Thu 11/48:00 a.m.YYZ - ORD
Nonstop1h 54mAir Canada
Sun 14/48:59 a.m.ORD - YYZ
Nonstop1h 53mAir Canada
Deal found 17/3C$ 347
Sat 23/38:25 a.m.YTZ - ORD
1 stop7h 22mAir Canada
Sun 31/31:58 p.m.ORD - YTZ
1 stop5h 43mAir Canada
Deal found 16/3C$ 451
Thu 28/32:35 p.m.YYZ - ORD
Nonstop2h 02mAir Canada
Sun 31/311:59 a.m.ORD - YYZ
Nonstop1h 53mAir Canada
Deal found 17/3C$ 485
Wed 27/310:00 a.m.YYZ - ORD
1 stop5h 47mAir Canada
Sat 30/311:00 a.m.ORD - YYZ
1 stop6h 36mAir Canada
Deal found 18/3C$ 506
  • If you’re travelling from Toronto to Chicago, one of the more common airlines travelling that route is Air Canada. Flights from Air Canada travelling this route typically cost C$ 240.73 RT. This price is typically 133% cheaper than other airlines that offer Toronto to Chicago flights. When booking this route, the cheapest RT price found was C$ 219. When travelling from Toronto to Chicago on Air Canada, the most popular airport to depart from is Toronto Pearson Intl Airport and the most popular airport to arrive at is Chicago O'Hare Intl Airport. When flying from Toronto to Chicago, Air Canada flights are 3% more popular than any other airline flying that same route.

Cheap Toronto to Chicago flights in March & April 2024

Find cheap flight options from Toronto to Chicago specifically for the months of March and April 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 525,491 searches. Prices were last updated on 19 March 2024.
Listed are some of the best fares we've found on flights departing from Toronto to Chicago in 2024. For more flight deals, be sure to check back very soon.
Tue 16/46:45 a.m.YKF - ORD
1 stop12h 01mMultiple Airlines
Tue 23/45:00 a.m.ORD - YKF
1 stop16h 55mMultiple Airlines
Deal found 18/3C$ 271
Tue 16/46:45 a.m.YKF - ORD
2 stops15h 00mMultiple Airlines
Tue 23/45:00 a.m.ORD - YKF
1 stop16h 55mMultiple Airlines
Deal found 18/3C$ 276
Fri 12/48:50 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Sun 14/48:40 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 18/3C$ 280
Fri 12/49:20 a.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Sun 14/48:40 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 18/3C$ 284
Tue 16/49:20 a.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Tue 23/48:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 18/3C$ 287
Wed 17/43:30 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Sat 20/48:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 18/3C$ 288
Thu 11/48:50 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Sun 14/48:40 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 18/3C$ 296
Tue 9/49:20 a.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Wed 17/45:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 18/3C$ 298
Mon 8/43:30 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Thu 11/48:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 18/3C$ 299

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 525,491 searches. Data last updated 19 March 2024.
Listed are some of the best fares we've found on flights departing from Toronto to Chicago in 2024. For more flight deals, be sure to check back very soon.
Tue 16/46:45 a.m.YKF - ORD
1 stop12h 01mMultiple Airlines
Tue 23/45:00 a.m.ORD - YKF
1 stop16h 55mMultiple Airlines
Deal found 18/3C$ 271
Tue 16/46:45 a.m.YKF - ORD
2 stops15h 00mMultiple Airlines
Tue 23/45:00 a.m.ORD - YKF
1 stop16h 55mMultiple Airlines
Deal found 18/3C$ 276
Fri 12/48:50 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Sun 14/48:40 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 18/3C$ 280
Fri 12/49:20 a.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Sun 14/48:40 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 18/3C$ 284
Tue 16/49:20 a.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Tue 23/48:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 18/3C$ 287
Wed 17/43:30 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Sat 20/48:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 18/3C$ 288
Fri 7/63:30 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Mon 10/65:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 18/3C$ 291
Sat 11/56:15 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Sun 19/58:40 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 17/3C$ 294
Thu 11/48:50 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Sun 14/48:40 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 18/3C$ 296

Direct 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 525,491 searches. Data last updated 19 March 2024.
Take a look at some of the direct flights travelling from Toronto to Chicago in the near future. Those looking to potentially save on 1 or 2-stop flights from Toronto to Chicago should utilize the search form at the top of the page.
Fri 12/48:50 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Sun 14/48:40 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 18/3C$ 280
Fri 12/49:20 a.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Sun 14/48:40 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 18/3C$ 284
Tue 16/49:20 a.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Tue 23/48:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 18/3C$ 287
Wed 17/43:30 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Sat 20/48:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 18/3C$ 288
Fri 7/63:30 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Mon 10/65:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 18/3C$ 291
Sat 11/56:15 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Sun 19/58:40 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 17/3C$ 294
Thu 11/48:50 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Sun 14/48:40 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 18/3C$ 296
Tue 9/49:20 a.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Wed 17/45:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 18/3C$ 298
Mon 8/43:30 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Thu 11/48:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 18/3C$ 299

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 525,491 searches. Data last updated 19 March 2024.
Have a look at some of the flights available from Toronto to Chicago departing last-minute. Tip: verify your flight details before completing your reservation.
Thu 28/39:30 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 31/35:30 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 17/3C$ 357
Sun 24/33:50 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Thu 11/45:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 17/3C$ 371
Thu 28/39:30 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Thu 4/48:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 17/3C$ 401
Sat 23/310:45 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 31/312:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 16/3C$ 402
Wed 27/33:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 31/35:30 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 17/3C$ 409
Mon 25/39:30 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 1/411:05 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 18/3C$ 424
Thu 28/39:30 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 1/48:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 18/3C$ 425
Tue 26/37:00 a.m.YYZ - ORD
2 stops15h 10mMultiple Airlines
Wed 27/38:42 p.m.ORD - YYZ
1 stop14h 13mMultiple Airlines
Deal found 18/3C$ 429
Sun 24/310:45 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 31/35:30 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 17/3C$ 439

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 525,491 searches. Data last updated 19 March 2024.
Take a look at some of the best available options we've come across on one-way flights from Toronto to Chicago. Those needing a return flight from Toronto to Chicago can use the search form above.
Wed 17/46:30 a.m.YYZ - ORD
1 stop12h 16mMultiple Airlines
Deal found 18/3C$ 164
Wed 17/46:30 a.m.YYZ - ORD
1 stop11h 15mMultiple Airlines
Deal found 17/3C$ 165
Mon 22/43:30 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Deal found 17/3C$ 165
Sun 21/48:50 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Deal found 17/3C$ 167
Wed 3/48:00 a.m.YKF - ORD
1 stop17h 10mMultiple Airlines
Deal found 18/3C$ 168
Fri 12/48:50 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Deal found 18/3C$ 168
Wed 10/43:30 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Deal found 18/3C$ 169
Sat 6/46:15 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Deal found 16/3C$ 172
Sun 14/410:30 a.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Deal found 17/3C$ 173

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 525,491 searches. Data last updated 19 March 2024.

Fly from

Any airport

Fly to

Any airport

Budget

C$ 271 - C$ 416

Route

Depart

Return

Price

Toronto Kitchener-WaterlooChicago O'Hare Intl

YKF - ORD

YKFORD

Toronto Kitchener-Waterloo

Tue 16/4

1 stop12h 01m

Chicago O'Hare Intl

Tue 23/4

1 stop16h 55m

C$ 271

Toronto Kitchener-WaterlooChicago O'Hare Intl

YKF - ORD

YKFORD

Toronto Kitchener-Waterloo

Tue 16/4

2 stops15h 00m

Chicago O'Hare Intl

Tue 23/4

1 stop16h 55m

C$ 276

Toronto IslandChicago Midway

YTZ - MDW

YTZMDW

Toronto Island

Fri 12/4

Nonstop1h 47m

Chicago Midway

Sun 14/4

Nonstop1h 42m

C$ 280

Toronto Pearson IntlChicago O'Hare Intl

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 10/4

Nonstop1h 55m

Chicago O'Hare Intl

Wed 17/4

Nonstop1h 45m

C$ 317

Toronto Pearson IntlChicago O'Hare Intl

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 11/4

Nonstop1h 54m

Chicago O'Hare Intl

Mon 15/4

Nonstop1h 43m

C$ 318

Toronto Pearson IntlChicago O'Hare Intl

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 16/4

Nonstop2h 01m

Chicago O'Hare Intl

Tue 23/4

1 stop5h 26m

C$ 348

Toronto Pearson IntlChicago O'Hare Intl

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 11/4

1 stop5h 05m

Chicago O'Hare Intl

Sun 14/4

1 stop4h 11m

C$ 356

Toronto Pearson IntlChicago O'Hare Intl

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 13/4

1 stop5h 37m

Chicago O'Hare Intl

Sun 14/4

Nonstop1h 45m

C$ 390

Toronto Pearson IntlChicago O'Hare Intl

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 8/6

1 stop5h 10m

Chicago O'Hare Intl

Mon 10/6

1 stop12h 16m

C$ 416

Flights are sorted by cheapest first

Deals found on 18/3

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 28 January 2024.
To ensure you get the cheapest price possible for a flight from Toronto to Chicago, you should look to book at least 78 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 17 March 2024.
Morning
Noon
Afternoon
Evening
All times are departure.
Travelers seeking maximum savings on their Toronto to Chicago flight should consider departing on Saturday evenings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Search Deals

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 C$ 168 while a round-trip flight costs C$ 330. Price data was last updated on 10 March 2024.

Currently, January is the cheapest month in which you can book a flight from Toronto to Chicago (average of C$ 261). Flying from Toronto to Chicago in August is currently the most expensive (average of C$ 434). 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

C$ 353

February

C$ 412

March

C$ 433

April

C$ 517

May

C$ 502

June

C$ 555

July

C$ 583

August

C$ 588

September

C$ 463

October

C$ 498

November

C$ 458

December

C$ 472

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

-5 - 23 °C

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 19 March 2024.
Get a feel of what it's like to fly with American Airlines, Air Canada and Delta from Toronto to Chicago by reading reviews from past customers. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
8.1
Very good
11,551 reviews

Food

7.5

Crew

8.6

Entertainment

8.1

Overall

8.1

Boarding

8.2

Comfort

7.9

Reviews

1 / 10

It was a good experience other than a short delay.

8.1
Very good
11,551 reviews
8.1
Very good
11,551 reviews

Food

7.5

Crew

8.6

Entertainment

8.1

Overall

8.1

Boarding

8.2

Comfort

7.9

Reviews

1 / 10

It was a good experience other than a short delay.

7.7
Good
2,809 reviews
8.1
Very good
11,551 reviews

Food

7.5

Crew

8.6

Entertainment

8.1

Overall

8.1

Boarding

8.2

Comfort

7.9

Reviews

1 / 10

It was a good experience other than a short delay.

7.5
Good
3,066 reviews
8.1
Very good
11,551 reviews

Food

7.5

Crew

8.6

Entertainment

8.1

Overall

8.1

Boarding

8.2

Comfort

7.9

Reviews

1 / 10

It was a good experience other than a short delay.

7.4
Good
460 reviews
8.1
Very good
11,551 reviews

Food

7.5

Crew

8.6

Entertainment

8.1

Overall

8.1

Boarding

8.2

Comfort

7.9

Reviews

1 / 10

It was a good experience other than a short delay.

7.4
Good
11,602 reviews
8.1
Very good
11,551 reviews

Food

7.5

Crew

8.6

Entertainment

8.1

Overall

8.1

Boarding

8.2

Comfort

7.9

Reviews

1 / 10

It was a good experience other than a short delay.

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.
  • 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.

  • How can passengers contribute to sustainability when flying from Toronto to Chicago?

    Pack a little if you want to minimize your carbon footprint when traveling from Toronto to Chicago. It is one of the easiest strategies for travelers to boost sustainable development. This is accurate since flying efficiently reduces the weight of the airplane, which in turn reduces fuel consumption. Before you even get to the runway, flying out of a green airport will reduce your carbon impact. These airports reduce their emissions through the use of alternative energy, the purchase of biofuels, or the application of green design principles during additions and upgrades.

  • What sustainability practices does Toronto Pearson International Airport offer?

    By 2030, Toronto Pearson International Airport (YYZ) wants to have net-zero carbon emissions. It includes "Scope 1" emissions from the fleet of vehicles and natural gas consumption of the airport, as well as "Scope 2" emissions from the production of the airport's electrical needs. The airport's Scope 2 emissions, which make up 93% of emission levels within its operational procedures, will be totally eradicated by cutting power use and transitioning to 100% green sources. Toronto Pearson  Airport will continue to prioritize operational management while concentrating on indirect "Scope 3" emissions.

  • Which alternative means of transportation is available along this route?

    If you intend to travel from Toronto to Chicago without adding to global warming emissions, a flight is your best bet. Flying is the most environmentally beneficial form of transportation since it allows for the most efficient long-distance transportation of people. However, you should opt for nonstop flights, as they consume less fuel per passenger as compared to connecting flights. Alternatively, you can opt for Amtrak trains which are more sustainable compared to trains as they produce at least 50% fewer carbon emissions. The best part is some of these trains adopt green energy; hence are sustainable.

  • 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 Multiple Airlines for just C$ 271, but on average you can expect to pay C$ 294.

  • 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$ 301.

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

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

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

    You can find direct flights on the following days: Tuesday, Wednesday.

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

    Per day, 2 flights depart from Toronto to Chicago on average.
    Afternoon (Noon - 6pm) - 100% of flight departures

  • How long is the flight from Toronto to Chicago?

    Airlines like Porter Airlines, American Airlines, and Air Canada fly from Toronto to Chicago in about 1h 47m. The time it takes to get you to your destination is usually consistent. Airlines will cover a distance of 703 km. Most flights 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 C$ 280 on this airline. Additional options worth looking into are American Airlines and Air Canada, starting at C$ 317 and C$ 318 round-trip. Users have found that Porter Airlines is 29% cheaper than the other options available to this destination.

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

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

  • 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: Lufthansa (100%), Republic Airways (97%), Copa Airlines (95%).

  • What are the cheapest flights from Toronto to Chicago?

    On average you can expect to pay C$ 1,479 for a flight from Toronto to Chicago. The cheapest flight overall is C$ 211 while the most popular route, (Toronto Pearson Intl - Chicago O'Hare Intl) is currently priced at C$ 315.

  • What does YYZ to ORD mean?

    YYZ and ORD are unique codes to identify airports used in the aviation industry. They are defined by IATA (International Air Transport Association) and are commonly called IATA codes. YYZ to ORD refers to a flight route from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport. 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).

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Fly from Toronto to Chicago on these airlines
Choose from the following airlines for your flight from Toronto to Chicago. Flights are based on user searches made on Cheapflights and were last updated on 19 March 2024.

Top 10 airlines flying from Toronto to Chicago

Discover the top 10 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 525,491 searches. Data last updated 19 March 2024.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 249AverageC$ 380FlexibilityNo cancel feeOn-time52%
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United AirlinesCheapestC$ 261AverageC$ 471FlexibilityNo cancel feeOn-time69%
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Air CanadaCheapestC$ 290AverageC$ 476FlexibilityNo cancel feeOn-time67%
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Air New ZealandCheapestC$ 296AverageC$ 326FlexibilityNo cancel feeOn-time78%
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ANACheapestC$ 321AverageC$ 435FlexibilityNo cancel feeOn-time80%
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Alaska AirlinesCheapestC$ 327AverageC$ 430FlexibilityNo cancel feeOn-time75%
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American AirlinesCheapestC$ 337AverageC$ 577FlexibilityNo cancel feeOn-time71%
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DeltaCheapestC$ 349AverageC$ 397FlexibilityNo cancel feeOn-timeN/A
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WestJetCheapestC$ 429AverageC$ 659FlexibilityNo cancel feeOn-time60%
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WestJet EncoreCheapestC$ 553AverageC$ 852FlexibilityNo cancel feeOn-timeN/A
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Helpful tips for your next trip to Chicago

Get useful tips and recommendations to enhance your travel experience on your next trip to Chicago. Learn about must-visit attractions, local customs, transportation options, weather conditions, and other valuable tips to make your trip more enjoyable and hassle-free.
  • Flights from Toronto to Chicago depart from Toronto Pearson International Airport (YYZ). The airport demonstrates its dedication to sustainability by using solar power to run its everyday activities.
  • United Airlines flying along this route endorses sustainability practices. The airline is adopting the use of Sustainable Aviation fuel (SAF) in its fleet and doing away with old planes while adopting modern ones which are fuel efficient.
  • Before booking your flight ticket, look for a green airport to reduce your carbon footprint. If you need information about sustainable airports like Chicago O’Hare (ORD), explore the carbon Airport Accreditation list.

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.

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 19 March 2024.
20%of flight departuresEarly morningMidnight to 6 am
33%of flight departuresMorning6 am to noon
42%of flight departuresAfternoonNoon to 6 pm
5%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 19 March 2024.
Sunday54daily flights
Monday57daily flights
Tuesday51daily flights
Wednesday48daily flights
Thursday57daily flights
Friday66daily flights
Saturday46daily flights

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

Deals for Toronto 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 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?

Cheapflights does show flights with no change fees to all users. To see these options for flights from Toronto to Chicago, users can toggle the no change fees filter when performing a flight search.

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

Yes, Cheapflights offers price alerts on Toronto to Chicago flights so you can book your travel at the perfect time. Price Alerts can be enabled by clicking the bell icon next to the flight deals above and providing your email address where you want to receive the alerts.

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