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Cheap flights from Toronto (YTO) to Chicago (CHI) from $131

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 9/12. 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
Jun 6 — Jun 131
From?
To?
Thu 6/6
Thu 6/13
1 adult, Economy
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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 June 1, 2024.

Popular in

September

Cheapest in

April

Round-trip from

$222

One-way from

$146
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 $337 1-2 weeks out and tickets from $489 for flights departing within the next 72 hours.

What is the cheapest month to fly from Toronto 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 $291 for the month, but tickets can be as low as $193. Due to multiple factors, prepare for potentially higher prices in September.

What is the cheapest time of day to fly from YTO to 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 2,810,401 searches. Data last updated June 1, 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.
Wed 9/49:00 pmYYZ - ORD
Nonstop2h 05mAir Canada
Wed 9/116:00 amORD - YYZ
Nonstop1h 37mAir Canada
Deal found 5/31$242
Mon 9/308:05 amYYZ - ORD
Nonstop1h 56mAir Canada
Sat 10/1211:00 amORD - YYZ
Nonstop1h 37mAir Canada
Deal found 5/31$246
Wed 9/47:30 amYYZ - ORD
1 stop6h 12mAir Canada
Sat 9/77:26 amORD - YYZ
Nonstop1h 32mAir Canada
Deal found 5/31$247
Tue 10/18:05 amYYZ - ORD
Nonstop1h 56mAir Canada
Tue 10/12:15 pmORD - YYZ
Nonstop1h 37mAir Canada
Deal found 6/1$250
Fri 10/47:00 amYYZ - ORD
Nonstop1h 56mAir Canada
Mon 10/79:18 pmORD - YYZ
Nonstop1h 40mAir Canada
Deal found 5/31$251
Wed 9/47:30 amYYZ - ORD
1 stop6h 12mAir Canada
Wed 9/112:00 pmORD - YYZ
1 stop6h 08mAir Canada
Deal found 5/31$252
Sat 6/87:50 pmYYZ - ORD
Nonstop1h 54mAir Canada
Tue 6/186:00 amORD - YYZ
Nonstop1h 48mAir Canada
Deal found 5/31$308
Thu 6/69:00 amYYZ - ORD
Nonstop1h 54mAir Canada
Thu 6/206:00 amORD - YYZ
Nonstop1h 48mAir Canada
Deal found 5/30$309
Thu 6/66:30 amYYZ - ORD
1 stop4h 31mAir Canada
Thu 6/206:00 amORD - YYZ
Nonstop1h 48mAir Canada
Deal found 5/30$314

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 2,810,401 searches. Data last updated June 1, 2024.
Have a look at some of the cheapest available United Airlines flights departing from Toronto and landing in Chicago. Make sure to examine the flight information before completing your reservation.
Wed 7/317:40 amYYZ - ORD
Nonstop1h 56mUnited Airlines
Tue 8/69:15 pmORD - YYZ
Nonstop1h 43mUnited Airlines
Deal found 5/30$243
Fri 10/47:00 amYYZ - ORD
Nonstop1h 56mUnited Airlines
Mon 10/79:35 pmORD - YYZ
1 stop9h 18mUnited Airlines
Deal found 5/31$260
Fri 8/169:00 pmYYZ - ORD
Nonstop2h 02mUnited Airlines
Mon 8/199:15 pmORD - YYZ
1 stop11h 49mUnited Airlines
Deal found 5/31$266
Sat 7/137:40 amYYZ - ORD
Nonstop1h 56mUnited Airlines
Mon 7/229:15 pmORD - YYZ
Nonstop1h 43mUnited Airlines
Deal found 5/31$267
Wed 9/252:00 pmYYZ - ORD
Nonstop1h 53mUnited Airlines
Tue 10/18:45 amORD - YYZ
1 stop4h 30mUnited Airlines
Deal found 5/30$269
Fri 8/166:00 pmYYZ - ORD
1 stop6h 17mUnited Airlines
Mon 8/199:15 pmORD - YYZ
1 stop11h 49mUnited Airlines
Deal found 5/31$271
Thu 6/67:43 pmYYZ - ORD
1 stop4h 37mUnited Airlines
Wed 6/199:15 pmORD - YYZ
Nonstop1h 43mUnited Airlines
Deal found 5/30$332
Sat 6/812:00 pmYYZ - ORD
Nonstop1h 54mUnited Airlines
Mon 6/179:15 pmORD - YYZ
Nonstop1h 43mUnited Airlines
Deal found 5/31$353
Tue 6/117:00 amYYZ - ORD
Nonstop1h 57mUnited Airlines
Tue 6/119:45 pmORD - YYZ
1 stop11h 19mUnited Airlines
Deal found 5/31$367

Cheap Toronto to Chicago flights in June & July 2024

Find cheap flight options from Toronto to Chicago specifically for the months of June and July 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,810,401 searches. Prices were last updated on June 1, 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.
Sun 6/3010:30 amYTZ - MDW
Nonstop1h 47mPorter Airlines
Thu 7/48:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/30$222
Tue 6/189:20 amYTZ - MDW
Nonstop1h 47mPorter Airlines
Tue 6/185:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/30$223
Thu 6/279:20 amYTZ - MDW
Nonstop1h 47mPorter Airlines
Mon 7/18:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 6/1$224
Mon 6/173:30 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
Tue 6/1811:05 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/30$226
Fri 6/283:30 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
Sat 6/2912:30 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/31$229
Fri 6/148:50 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
Fri 6/218:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/31$233
Thu 6/273:30 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
Mon 7/18:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/31$234
Sat 6/296:15 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
Sat 7/68:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/30$236
Fri 6/147:55 amYYZ - ORD
Nonstop1h 56mAir Canada
Sat 6/159:15 pmORD - YYZ
Nonstop1h 43mAir Canada
Deal found 5/31$242

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 2,810,401 searches. Data last updated June 1, 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.
Sun 6/3010:30 amYTZ - MDW
Nonstop1h 47mPorter Airlines
Thu 7/48:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/30$222
Tue 6/189:20 amYTZ - MDW
Nonstop1h 47mPorter Airlines
Tue 6/185:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/30$223
Thu 6/279:20 amYTZ - MDW
Nonstop1h 47mPorter Airlines
Mon 7/18:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 6/1$224
Fri 9/273:30 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
Thu 10/38:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/30$225
Mon 6/173:30 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
Tue 6/1811:05 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/30$226
Wed 7/109:20 amYTZ - MDW
Nonstop1h 47mPorter Airlines
Thu 7/188:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/31$229
Thu 9/263:30 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
Sun 9/298:40 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/30$230
Thu 7/118:50 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
Fri 7/1911:30 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/31$231
Fri 6/148:50 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
Fri 6/218:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/31$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 2,810,401 searches. Data last updated June 1, 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.
Thu 6/279:20 amYTZ - MDW
Nonstop1h 47mPorter Airlines
Sun 6/308:40 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/30$217
Mon 7/18:50 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
Thu 7/411:30 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/31$218
Fri 6/143:30 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
Mon 6/178:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/31$220
Fri 7/128:50 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
Sun 7/218:40 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/31$221
Sun 6/3010:30 amYTZ - MDW
Nonstop1h 47mPorter Airlines
Thu 7/48:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/30$222
Tue 6/189:20 amYTZ - MDW
Nonstop1h 47mPorter Airlines
Tue 6/185:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/30$223
Thu 6/279:20 amYTZ - MDW
Nonstop1h 47mPorter Airlines
Mon 7/18:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 6/1$224
Fri 9/273:30 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
Thu 10/38:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/30$225
Mon 6/173:30 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
Tue 6/1811:05 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/30$226

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 2,810,401 searches. Data last updated June 1, 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.
Tue 6/1112:30 pmYYZ - ORD
1 stop7h 04mDelta
Sat 6/1512:35 pmORD - YYZ
1 stop9h 37mDelta
Deal found 5/30$281
Fri 6/75:58 pmYYZ - ORD
1 stop4h 00mDelta
Fri 6/218:30 amORD - YYZ
1 stop7h 38mDelta
Deal found 5/30$289
Sat 6/86:30 amYYZ - ORD
2 stops13h 02mMultiple Airlines
Tue 6/116:40 pmORD - YYZ
1 stop25h 45mMultiple Airlines
Deal found 5/31$299
Mon 6/104:15 pmYYZ - ORD
2 stops26h 25mMultiple Airlines
Fri 6/145:34 pmORD - YYZ
1 stop15h 19mMultiple Airlines
Deal found 5/31$306
Sat 6/87:50 pmYYZ - ORD
Nonstop1h 54mAir Canada
Tue 6/186:00 amORD - YYZ
Nonstop1h 48mAir Canada
Deal found 5/31$308
Thu 6/69:00 amYYZ - ORD
Nonstop1h 54mAir Canada
Thu 6/206:00 amORD - YYZ
Nonstop1h 48mAir Canada
Deal found 5/30$309
Fri 6/75:58 pmYYZ - ORD
1 stop4h 00mDelta
Sat 6/221:25 pmORD - YYZ
1 stop8h 25mDelta
Deal found 5/30$312
Thu 6/66:30 amYYZ - ORD
1 stop4h 31mAir Canada
Thu 6/206:00 amORD - YYZ
Nonstop1h 48mAir Canada
Deal found 5/30$314
Tue 6/112:00 pmYYZ - ORD
Nonstop1h 54mMultiple Airlines
Sat 6/156:00 amORD - YYZ
Nonstop1h 45mMultiple Airlines
Deal found 5/30$316

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 2,810,401 searches. Data last updated June 1, 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.
Thu 9/123:30 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
Deal found 5/31$131
Mon 6/178:50 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
Deal found 5/31$132
Sun 6/308:50 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
Deal found 5/30$133
Sun 8/1110:30 amYTZ - MDW
Nonstop1h 47mPorter Airlines
Deal found 5/31$134
Thu 6/279:20 amYTZ - MDW
Nonstop1h 47mPorter Airlines
Deal found 5/30$135
Fri 6/148:50 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
Deal found 5/31$136
Fri 7/263:30 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
Deal found 5/30$137
Sat 6/1510:45 amYTZ - MDW
Nonstop1h 47mPorter Airlines
Deal found 5/30$141
Fri 6/149:00 pmYYZ - ORD
Nonstop2h 02mAir Canada
Deal found 5/31$142

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 2,810,401 searches. Data last updated June 1, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$217 - $301

Route

Depart

Return

Price

Toronto IslandChicago Midway

YTZ - MDW

YTZMDW

Toronto Island

Thu 6/27

Nonstop1h 47m

Chicago Midway

Sun 6/30

Nonstop1h 42m

$217

Toronto IslandChicago Midway

YTZ - MDW

YTZMDW

Toronto Island

Mon 7/1

Nonstop1h 47m

Chicago Midway

Thu 7/4

Nonstop1h 42m

$218

Toronto Pearson IntlChicago O'Hare Intl

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 10/19

1 stop5h 01m

Chicago O'Hare Intl

Tue 10/22

1 stop7h 18m

$240

Toronto Pearson IntlChicago O'Hare Intl

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 9/4

Nonstop2h 05m

Chicago O'Hare Intl

Wed 9/11

Nonstop1h 37m

$242

Toronto Pearson IntlChicago O'Hare Intl

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 7/31

Nonstop1h 56m

Chicago O'Hare Intl

Tue 8/6

Nonstop1h 43m

$243

Toronto Pearson IntlChicago O'Hare Intl

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 6/18

Nonstop1h 55m

Chicago O'Hare Intl

Wed 6/26

1 stop8h 29m

$255

Toronto Pearson IntlChicago O'Hare Intl

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 9/5

1 stop4h 31m

Chicago O'Hare Intl

Mon 9/9

Nonstop1h 37m

$258

Toronto Pearson IntlChicago O'Hare Intl

YYZ - ORD

YYZORD

Toronto Pearson Intl

Mon 10/7

Nonstop1h 56m

Chicago O'Hare Intl

Thu 10/10

Nonstop1h 32m

$264

Toronto Pearson IntlChicago O'Hare Intl

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 6/22

1 stop4h 05m

Chicago O'Hare Intl

Tue 6/25

1 stop4h 33m

$301

Flights are sorted by cheapest first

Deals found on 5/30

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 May 24, 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

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 May 26, 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. Friday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
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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

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 June 1, 2024.
Read through reviews of airlines operating flights from Toronto to Chicago, such as Air Canada, United Airlines and Delta. 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
10,410 reviews
Check prices

Food

7.4

Comfort

7.9

Entertainment

8.0

Crew

8.6

Boarding

8.2

Overall

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
10,410 reviews
Delta
8.0
Very good
10,410 reviews
Check prices

Food

7.4

Comfort

7.9

Entertainment

8.0

Crew

8.6

Boarding

8.2

Overall

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
1,512 reviews
Delta
8.0
Very good
10,410 reviews
Check prices

Food

7.4

Comfort

7.9

Entertainment

8.0

Crew

8.6

Boarding

8.2

Overall

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
2,866 reviews
Delta
8.0
Very good
10,410 reviews
Check prices

Food

7.4

Comfort

7.9

Entertainment

8.0

Crew

8.6

Boarding

8.2

Overall

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
388 reviews
Delta
8.0
Very good
10,410 reviews
Check prices

Food

7.4

Comfort

7.9

Entertainment

8.0

Crew

8.6

Boarding

8.2

Overall

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.

United Airlines
7.4
Good
10,754 reviews
Delta
8.0
Very good
10,410 reviews
Check prices

Food

7.4

Comfort

7.9

Entertainment

8.0

Crew

8.6

Boarding

8.2

Overall

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 Porter Airlines for just $217, but on average you can expect to pay $229.

  • 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 $229.

  • 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: Tuesday, Saturday.

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

    8 flight departures from Toronto to Chicago per day on average.
    Early Morning (Midnight to 6am) - 63% of flight departures
    Afternoon (Noon - 6pm) - 38% of flight departures

  • How long is the flight from Toronto to Chicago?

    Porter Airlines, Delta, and Air Canada can get you from Toronto to Chicago in just under 1h 47m. Your travel time can differ by up to 3h 14m. There are 437 mi between Toronto and Chicago. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 Delta and Air Canada, starting at $240 and $242 round-trip. Porter Airlines is currently priced 25% below the average price you’ll pay for this route.

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

    For one-way options, check prices for Porter Airlines. According to our data, you can fly for as low as $131. Users have also found prices from $142 and $146 on Air Canada and United Airlines, respectively.

  • 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 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 $3,018, our data indicates the cheapest price to be $146. The most popular route (Toronto Pearson Intl - Chicago O'Hare Intl), is priced around $243.

  • 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 6/1.

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

    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 $326). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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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.

Pierre Elliott Trudeau Intl to O'Hare Intl flights
Pearson 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
Ottawa to O'Hare Intl flights
Pearson Intl to St. Louis flights
Hamilton to O'Hare Intl flights
London to O'Hare Intl flights
Pierre Elliott Trudeau Intl to St. Louis flights
Ottawa to St. Louis flights
London to Midway flights
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Pearson Intl to Peoria 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 2,810,401 searches. Data last updated June 1, 2024.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$206Average$286FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
Air CanadaCheapest$214Average$358FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
United AirlinesCheapest$233Average$349FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
American AirlinesCheapest$242Average$399FlexibilityNo 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 June 1, 2024.
10%of flight departuresEarly morningMidnight to 6 am
34%of flight departuresMorning6 am to noon
42%of flight departuresAfternoonNoon to 6 pm
14%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 June 1, 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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