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Cheap flights from Toronto to Chicago from C$ 171

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 28/8. Fares are subject to change and may not be available on all flights or dates of travel.
YTO — CHI
30 Jul — 6 Aug1
1 adult
Tue 30/7
Tue 6/8

The best prices from Toronto to Chicago are usually found in April or February, booked 87 days in advance, depart on a Monday or Saturday and return on a Tuesday

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 25 July 2024.

Round-trip from

C$ 278

One-way from

C$ 171

Popular in

September

Cheapest in

April
Porter Airlines
  • Porter Airlines
  • 19/9-23/9
  • Nonstop
  • 3h 29m total
  • Toronto to Chicago
Porter Airlines
  • Porter Airlines
  • 28/8
  • Nonstop
  • 1h 47m total
  • Toronto to Chicago
High demand for flights, 15% potential price rise
Best time to find cheap flights, 14% potential price drop

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

Sunday is generally a great day to depart. Flying on this day could help you save up to 10%.

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

Find a great deal and save up to 97% by booking at least 38 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$ 415.

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

April is one of the best times of the year to fly to Chicago from Toronto. Prices for April average C$ 384 per person but you can even find prices for as low as C$ 267. The most expensive prices can be found in the month of September. Opting for a April flight can save you 18% on your journey compared to booking in September

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

Unlike at noon, when flights are generally more expensive, you can save up to 12% on flights from Toronto to Chicago by exploring options for tickets in the evening.

Cheap United Airlines flights from Toronto to Chicago

Explore cheap flight options specifically provided by United 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 435,117 searches. Data last updated 25 July 2024.
Take a look at some of the lowest-priced United Airlines flights heading from Toronto to Chicago. It's recommended that users confirm their flight details before booking.
Tue 13/89:00 p.m.YYZ - ORD
Nonstop2h 02mUnited Airlines
Sat 17/812:15 p.m.ORD - YYZ
1 stop8h 59mUnited Airlines
Deal found 24/7C$ 364
Thu 8/87:40 a.m.YYZ - ORD
Nonstop1h 56mUnited Airlines
Sat 10/89:28 p.m.ORD - YYZ
1 stop9h 30mUnited Airlines
Deal found 24/7C$ 397
Fri 23/82:00 p.m.YYZ - ORD
Nonstop1h 54mUnited Airlines
Sat 31/87:45 p.m.ORD - YYZ
1 stop11h 48mUnited Airlines
Deal found 24/7C$ 402
Wed 14/89:00 p.m.YYZ - ORD
Nonstop2h 02mUnited Airlines
Sat 17/86:00 p.m.ORD - YYZ
Nonstop1h 43mUnited Airlines
Deal found 24/7C$ 406
Fri 2/87:00 a.m.YYZ - ORD
Nonstop1h 57mUnited Airlines
Thu 8/86:00 a.m.ORD - YYZ
Nonstop1h 48mUnited Airlines
Deal found 25/7C$ 452
Sun 4/89:00 p.m.YYZ - ORD
1 stop11h 41mUnited Airlines
Thu 15/82:15 p.m.ORD - YYZ
Nonstop1h 48mUnited Airlines
Deal found 24/7C$ 459
Sat 3/87:43 p.m.YYZ - ORD
1 stop4h 32mUnited Airlines
Sat 10/86:00 p.m.ORD - YYZ
Nonstop1h 43mUnited Airlines
Deal found 25/7C$ 467
Thu 1/89:00 p.m.YYZ - ORD
1 stop13h 40mUnited Airlines
Wed 7/89:15 p.m.ORD - YYZ
Nonstop1h 43mUnited Airlines
Deal found 24/7C$ 489
Thu 1/89:00 p.m.YYZ - ORD
Nonstop2h 02mUnited Airlines
Tue 6/812:45 p.m.ORD - YYZ
1 stop8h 29mUnited Airlines
Deal found 25/7C$ 546
  • One of the most popular airlines travelling from Toronto to Chicago is United Airlines. Flights on this route from United Airlines typically cost C$ 321.64 RT, a price that is 113% more expensive than the average Toronto to Chicago flight. The cheapest flight found was C$ 237 RT. 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, United 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 435,117 searches. Data last updated 25 July 2024.
Browse through some of the cheapest Air Canada flights travelling from Toronto to Chicago. Deals frequently update to provide users with more options.
Sat 7/93:20 p.m.YTZ - ORD
1 stop5h 50mAir Canada
Sun 8/910:55 a.m.ORD - YTZ
1 stop5h 54mAir Canada
Deal found 25/7C$ 308
Thu 22/87:00 a.m.YYZ - ORD
Nonstop1h 56mAir Canada
Sun 25/86:00 a.m.ORD - YYZ
Nonstop1h 48mAir Canada
Deal found 25/7C$ 314
Sat 7/94:00 p.m.YYZ - ORD
1 stop5h 10mAir Canada
Tue 10/99:18 p.m.ORD - YYZ
Nonstop1h 40mAir Canada
Deal found 24/7C$ 315
Thu 22/87:40 a.m.YYZ - ORD
Nonstop1h 56mAir Canada
Mon 26/86:00 a.m.ORD - YYZ
Nonstop1h 48mAir Canada
Deal found 25/7C$ 321
Sun 15/97:00 a.m.YYZ - ORD
Nonstop1h 56mAir Canada
Wed 18/91:02 p.m.ORD - YYZ
Nonstop1h 41mAir Canada
Deal found 24/7C$ 322
Thu 22/87:50 p.m.YYZ - ORD
Nonstop1h 54mAir Canada
Sun 25/86:00 a.m.ORD - YYZ
Nonstop1h 48mAir Canada
Deal found 25/7C$ 328
Sat 7/97:50 p.m.YYZ - ORD
Nonstop1h 53mAir Canada
Wed 11/97:25 a.m.ORD - YYZ
1 stop4h 43mAir Canada
Deal found 24/7C$ 329
Thu 22/88:10 a.m.YYZ - ORD
1 stop5h 32mAir Canada
Sun 25/86:00 a.m.ORD - YYZ
Nonstop1h 48mAir Canada
Deal found 24/7C$ 332
Thu 8/87:00 a.m.YYZ - ORD
Nonstop1h 57mAir Canada
Sun 11/86:00 a.m.ORD - YYZ
Nonstop1h 48mAir Canada
Deal found 25/7C$ 333
  • 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 128% 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 July & August 2024

Find cheap flight options from Toronto to Chicago specifically for the months of July and August 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 435,117 searches. Prices were last updated on 25 July 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.
Thu 22/89:20 a.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Sun 1/98:25 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 24/7C$ 292
Fri 23/83:30 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Sat 31/88:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 24/7C$ 293
Mon 19/88:50 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Tue 3/911:05 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 24/7C$ 294
Thu 8/83:30 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Tue 13/811:05 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 24/7C$ 297
Thu 22/88:50 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Thu 29/88:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 25/7C$ 300
Wed 21/83:30 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Wed 28/85:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 24/7C$ 301
Wed 7/88:50 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Sun 11/812:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 24/7C$ 304
Fri 23/83:30 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Mon 26/811:30 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 25/7C$ 305
Thu 22/83:30 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Sun 25/88:40 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 25/7C$ 307

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 435,117 searches. Data last updated 25 July 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.
Thu 19/98:50 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Mon 23/98:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 25/7C$ 278
Thu 19/93:30 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Mon 23/95:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 24/7C$ 287
Thu 22/89:20 a.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Sun 1/98:25 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 24/7C$ 292
Fri 23/83:30 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Sat 31/88:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 24/7C$ 293
Mon 19/88:50 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Tue 3/911:05 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 24/7C$ 294
Thu 8/83:30 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Tue 13/811:05 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 24/7C$ 297
Mon 9/99:20 a.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Fri 13/98:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 24/7C$ 299
Thu 22/88:50 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Thu 29/88:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 25/7C$ 300
Wed 21/83:30 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Wed 28/85:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 24/7C$ 301

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 435,117 searches. Data last updated 25 July 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.
Thu 19/93:30 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Mon 23/95:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 24/7C$ 287
Thu 22/89:20 a.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Sun 1/98:25 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 24/7C$ 292
Fri 23/83:30 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Sat 31/88:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 24/7C$ 293
Mon 19/88:50 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Tue 3/911:05 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 24/7C$ 294
Thu 8/83:30 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Tue 13/811:05 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 24/7C$ 297
Mon 9/99:20 a.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Fri 13/98:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 24/7C$ 299
Thu 22/88:50 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Thu 29/88:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 25/7C$ 300
Wed 21/83:30 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Wed 28/85:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 24/7C$ 301
Wed 7/88:50 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Sun 11/812:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 24/7C$ 304

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 435,117 searches. Data last updated 25 July 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.
Sat 3/86:15 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Fri 9/85:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 24/7C$ 384
Sun 4/810:30 a.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Wed 7/85:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 24/7C$ 390
Fri 2/88:50 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Fri 9/85:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 24/7C$ 398
Thu 1/89:00 p.m.YYZ - ORD
Nonstop2h 02mAir Canada
Wed 7/84:00 p.m.ORD - YYZ
Nonstop1h 48mAir Canada
Deal found 24/7C$ 399
Sun 4/87:40 a.m.YYZ - ORD
Nonstop1h 56mAir Canada
Tue 6/86:00 p.m.ORD - YYZ
Nonstop1h 43mAir Canada
Deal found 23/7C$ 405
Sat 3/86:15 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Tue 6/85:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 23/7C$ 405
Sat 3/87:00 a.m.YYZ - ORD
Nonstop1h 57mAir Canada
Sat 10/86:00 p.m.ORD - YYZ
Nonstop1h 43mAir Canada
Deal found 25/7C$ 412
Sun 4/86:30 a.m.YYZ - ORD
Nonstop1h 55mAmerican Airlines
Wed 7/811:54 a.m.ORD - YYZ
Nonstop1h 35mAmerican Airlines
Deal found 24/7C$ 413
Sat 3/86:15 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Wed 7/88:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 24/7C$ 413

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 435,117 searches. Data last updated 25 July 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 28/88:50 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Deal found 25/7C$ 171
Sat 10/86:15 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Deal found 24/7C$ 173
Sun 22/98:50 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Deal found 24/7C$ 177
Sun 18/810:30 a.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Deal found 25/7C$ 178
Wed 14/88:50 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Deal found 24/7C$ 180
Thu 22/88:50 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Deal found 25/7C$ 181
Sun 22/98:50 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Deal found 25/7C$ 182
Mon 26/83:30 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Deal found 25/7C$ 185
Thu 29/89:20 a.m.YTZ - ORD
1 stop4h 22mAir Canada
Deal found 24/7C$ 185

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 435,117 searches. Data last updated 25 July 2024.

Fly from

Any airport

Fly to

Any airport

Budget

C$ 278 - C$ 444

Route

Depart

Return

Price

Toronto IslandChicago Midway

YTZ - MDW

YTZMDW

Toronto Island

Thu 19/9

Nonstop1h 47m

Chicago Midway

Mon 23/9

Nonstop1h 42m

C$ 278

Toronto IslandChicago O'Hare Intl

YTZ - ORD

YTZORD

Toronto Island

Sat 7/9

1 stop5h 50m

Chicago O'Hare Intl

Sun 8/9

1 stop5h 54m

C$ 308

Toronto IslandChicago Midway

YTZ - MDW

YTZMDW

Toronto Island

Thu 8/8

Nonstop1h 47m

Chicago Midway

Sun 11/8

Nonstop1h 42m

C$ 334

Toronto Pearson IntlChicago O'Hare Intl

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 7/8

Nonstop2h 02m

Chicago O'Hare Intl

Sun 11/8

Nonstop1h 48m

C$ 344

Toronto Pearson IntlChicago O'Hare Intl

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 21/8

Nonstop1h 54m

Chicago O'Hare Intl

Wed 28/8

1 stop6h 34m

C$ 358

Toronto Pearson IntlChicago O'Hare Intl

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 4/9

1 stop5h 02m

Chicago O'Hare Intl

Tue 10/9

1 stop5h 50m

C$ 362

Toronto Pearson IntlChicago O'Hare Intl

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 13/8

Nonstop2h 02m

Chicago O'Hare Intl

Sat 17/8

1 stop8h 59m

C$ 364

Toronto Pearson IntlChicago O'Hare Intl

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 14/8

Nonstop1h 55m

Chicago O'Hare Intl

Sun 18/8

Nonstop1h 50m

C$ 420

Toronto Pearson IntlChicago O'Hare Intl

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 15/8

1 stop4h 01m

Chicago O'Hare Intl

Mon 19/8

1 stop4h 23m

C$ 444

Flights are sorted by cheapest first

Deals found on 25/7

How far ahead should I 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 23 July 2024.
To ensure you get the cheapest price possible for a flight from Toronto to Chicago, you should look to book at least 87 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

What is the cheapest day 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 21 July 2024.
Morning
Noon
Afternoon
Evening
All times are departure.
Travelers seeking maximum savings on their Toronto to Chicago flight should consider departing on Tuesday 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

Best time to book a flight from Toronto to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Toronto 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

-5 - 23 °C

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -5.0 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 25 July 2024.
Get a feel of what it's like to fly with United Airlines, Air Canada and American Airlines 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
9,365 reviews

Overall

8.1

Entertainment

7.2

Food

7.2

Boarding

8.2

Comfort

7.9

Crew

8.6

Reviews

1 / 10

A/C was not working on the ground so it was 110 degrees on the plane when we boarded and we sat there for almost 40 minutes because Austin’s gate system has not kept up with growth. Not Alaska’s fault 100% but it was miserable.

8.1
Very good
9,365 reviews
8.1
Very good
9,365 reviews

Overall

8.1

Entertainment

7.2

Food

7.2

Boarding

8.2

Comfort

7.9

Crew

8.6

Reviews

1 / 10

A/C was not working on the ground so it was 110 degrees on the plane when we boarded and we sat there for almost 40 minutes because Austin’s gate system has not kept up with growth. Not Alaska’s fault 100% but it was miserable.

8.0
Very good
9,630 reviews
8.1
Very good
9,365 reviews

Overall

8.1

Entertainment

7.2

Food

7.2

Boarding

8.2

Comfort

7.9

Crew

8.6

Reviews

1 / 10

A/C was not working on the ground so it was 110 degrees on the plane when we boarded and we sat there for almost 40 minutes because Austin’s gate system has not kept up with growth. Not Alaska’s fault 100% but it was miserable.

7.8
Good
414 reviews
8.1
Very good
9,365 reviews

Overall

8.1

Entertainment

7.2

Food

7.2

Boarding

8.2

Comfort

7.9

Crew

8.6

Reviews

1 / 10

A/C was not working on the ground so it was 110 degrees on the plane when we boarded and we sat there for almost 40 minutes because Austin’s gate system has not kept up with growth. Not Alaska’s fault 100% but it was miserable.

7.6
Good
344 reviews
8.1
Very good
9,365 reviews

Overall

8.1

Entertainment

7.2

Food

7.2

Boarding

8.2

Comfort

7.9

Crew

8.6

Reviews

1 / 10

A/C was not working on the ground so it was 110 degrees on the plane when we boarded and we sat there for almost 40 minutes because Austin’s gate system has not kept up with growth. Not Alaska’s fault 100% but it was miserable.

7.4
Good
10,000 reviews
8.1
Very good
9,365 reviews

Overall

8.1

Entertainment

7.2

Food

7.2

Boarding

8.2

Comfort

7.9

Crew

8.6

Reviews

1 / 10

A/C was not working on the ground so it was 110 degrees on the plane when we boarded and we sat there for almost 40 minutes because Austin’s gate system has not kept up with growth. Not Alaska’s fault 100% but it was miserable.

Toronto to Chicago Travel Guide

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.

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.
  • 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.

  • 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.

  • 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.

  • 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 Porter Airlines for just C$ 278, but on average you can expect to pay C$ 301.

  • 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$ 304.

  • 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: Monday, Thursday, Friday, Saturday.

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

    Per day, 16 flights depart from Toronto to Chicago on average.
    Morning (6am - Midday) - 88% of flight departures
    Afternoon (Noon - 6pm) - 13% of flight departures

  • How long is the flight from Toronto to Chicago?

    Airlines like Porter Airlines and Air Canada fly from Toronto to Chicago in about 1h 47m. The time it takes to get you to your destination can typically vary by up to 4h 03m. Airlines will cover a distance of 703 km. When browsing for deals, the options you’ll see will be for both direct flights and flights with stops.

  • 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$ 278 on this airline. An additional option worth looking into is Air Canada, starting at C$ 308. Users have found that Porter Airlines is 27% cheaper than the other options available to this destination.

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

    The cheapest airlines for a one-way flight from Toronto to Chicago are Porter Airlines (C$ 171), Air Canada (C$ 185), and United Airlines (C$ 200).

  • What are the most popular routes 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: Republic Airways (93%), Japan Airlines (90%), Copa Airlines (88%).

  • What are the cheapest flights from Toronto to Chicago?

    On average you can expect to pay C$ 1,603 for a flight from Toronto to Chicago. The cheapest flight overall is C$ 207 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).

  • 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 25/7.

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

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

    Currently, January is the cheapest month in which you can book a flight from Toronto to Chicago (average of C$ 259). Flying from Toronto to Chicago in October is currently the most expensive (average of C$ 357). 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.

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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 25 July 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 435,117 searches. Data last updated 25 July 2024.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 196AverageC$ 443FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
United AirlinesCheapestC$ 250AverageC$ 443FlexibilityNo cancel feeOn-time69%
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Porter AirlinesCheapestC$ 263AverageC$ 355FlexibilityNo cancel feeOn-time52%
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Air New ZealandCheapestC$ 303AverageC$ 333FlexibilityNo cancel feeOn-time78%
Search Air New Zealand flights
ANACheapestC$ 327AverageC$ 445FlexibilityNo cancel feeOn-time80%
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Alaska AirlinesCheapestC$ 334AverageC$ 439FlexibilityNo cancel feeOn-time75%
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DeltaCheapestC$ 352AverageC$ 380FlexibilityNo cancel feeOn-timeN/A
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American AirlinesCheapestC$ 364AverageC$ 524FlexibilityNo cancel feeOn-time71%
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WestJetCheapestC$ 438AverageC$ 644FlexibilityNo cancel feeOn-time60%
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WestJet EncoreCheapestC$ 466AverageC$ 870FlexibilityNo cancel feeOn-timeN/A
Search WestJet Encore flights

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 25 July 2024.
1%of flight departuresEarly morningMidnight to 6 am
34%of flight departuresMorning6 am to noon
45%of flight departuresAfternoonNoon to 6 pm
20%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 25 July 2024.
Sunday54daily flights
Monday57daily flights
Tuesday51daily flights
Wednesday48daily flights
Thursday57daily flights
Friday66daily flights
Saturday46daily flights

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?

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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