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

Our cheapest airline available from Toronto to Chicago is United Airlines. Our recent data shows that you can find tickets from as low as $233 on this airline. Additional options worth looking into are Porter Airlines and Air Canada, starting at $234 and $237 round-trip. United Airlines is currently priced 14% 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 Air Canada. According to our data, you can fly for as low as $140. Users have also found prices from $141 and $141 on United Airlines and Porter Airlines, respectively.

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

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.

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

Currently, August is the cheapest month in which you can book a flight from Toronto to Chicago (average of $245). Flying from Toronto to Chicago in March is currently the most expensive (average of $318). 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.

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

Travelers seeking maximum savings on their Toronto to Chicago flight should consider departing on Monday evenings when fares are most often at their lowest. Monday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Toronto to Chicago

The most flights from YTO to CHI are scheduled on a Monday (54 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (46 on average).

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

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 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 Pearson Intl - Chicago Midway and Toronto Island - Chicago Midway.

What are the cheapest flights from Toronto to Chicago?

Looking for the cheapest flight from Toronto to Chicago? While on average our users pay $817, our data indicates the cheapest price to be $155. The most popular route (Toronto Pearson Intl - Chicago O'Hare Intl), is priced around $233.

What are the most reliable airlines from Toronto to Chicago?

Consider Royal Jordanian (96%), Japan Airlines (95%) or Emirates (92%) when booking your flight. These represent the most reliable airlines when flying from Toronto to Chicago.

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 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 91% on this flight, we recommend booking at least 35 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 $292 1-2 weeks out and tickets from $486 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 $272 for the month, but tickets can be as low as $193. Due to multiple factors, prepare for potentially higher prices in December.

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 18% on your trip compared to booking a flight at noon.

Most accurate provider : When it comes to deals on Toronto-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Toronto-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Toronto-Chicago flight searches over the past month and is updated monthly.

Most trusted provider : When it comes to deals on Toronto-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Toronto-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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.

$140+ Flights from Toronto to Chicago

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1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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

Cheap flight deals from Toronto to Chicago

Most accurate provider	FlightHub 3 stars
Most trusted provider	FlightHub 3 stars
Round-trip from	$233 (United Airlines)
One-way from	$140 (Mytrip)
Popular in	December
Cheapest in	April
Average price	$285

Provider with most accurate pricing for Toronto (YTO)-Chicago (CHI) flight deals.

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Provider most trusted by Cheapflights users for Toronto (YTO)-Chicago (CHI) flights.

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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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High demand for flights, 7% potential price rise

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Best time to find cheap flights, 1% potential price drop

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Average for round-trip flights in January 2025

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Find flight deals from Toronto to Chicago

Cheapest flights from Toronto to Chicago
Explore the most affordable flight options available from Toronto to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 13, 2025.

Thu 2/612:20 pmYYZ - ORD

Nonstop1h 51mUnited Airlines

Thu 2/68:30 pmORD - YYZ

Nonstop1h 41mUnited Airlines

Deal found 1/12

$233

Fri 2/1411:20 amYTZ - MDW

Nonstop1h 50mPorter Airlines

Mon 2/171:05 pmMDW - YTZ

Nonstop1h 42mPorter Airlines

Deal found 1/13

$234

Sat 2/110:25 amYTZ - ORD

1 stop5h 20mAir Canada

Mon 2/31:55 pmORD - YTZ

1 stop5h 48mAir Canada

Deal found 1/11

$237

Thu 2/66:40 pmYYZ - ORD

Nonstop1h 57mAir Canada

Sun 2/911:35 amORD - YYZ

1 stop6h 00mAir Canada

Deal found 1/12

$238

Tue 2/47:05 amYYZ - ORD

1 stop14h 08mMultiple Airlines

Thu 2/66:55 amORD - YYZ

1 stop16h 00mMultiple Airlines

Deal found 1/12

$243

Thu 2/611:20 amYTZ - MDW

Nonstop1h 50mAir Transat

Sun 2/91:05 pmMDW - YTZ

Nonstop1h 42mAir Transat

Deal found 1/12

$246

Thu 2/63:30 pmYYZ - ORD

Nonstop2h 11mLufthansa

Sun 2/96:28 pmORD - YYZ

Nonstop1h 57mLufthansa

Deal found 1/12

$251

Thu 2/66:00 amYYZ - ORD

1 stop4h 16mDelta

Sun 2/94:58 pmORD - YYZ

1 stop4h 51mDelta

Deal found 1/13

$263

Thu 2/66:30 amYYZ - MDW

1 stop7h 12mDelta

Sun 2/95:05 pmMDW - YYZ

1 stop4h 44mDelta

Deal found 1/13

$263

Thu 2/136:00 amYYZ - ORD

1 stop5h 38mAmerican Airlines

Wed 2/198:11 amORD - YYZ

Nonstop1h 40mAmerican Airlines

Deal found 1/12

$279

Tue 2/47:00 amYTZ - ORD

2 stops14h 13mMultiple Airlines

Thu 2/66:55 amORD - YTZ

2 stops14h 20mMultiple Airlines

Deal found 1/12

$287

Mon 2/246:30 amYYZ - MDW

1 stop7h 12mWestJet

Wed 2/2610:19 amMDW - YYZ

2 stops12h 14mWestJet

Deal found 1/11

$293

Best flights from Toronto to Chicago
Discover carefully curated flight deals from Toronto to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated January 13, 2025.

Thu 2/612:20 pmYYZ - ORD

Nonstop1h 51mUnited Airlines

Thu 2/68:30 pmORD - YYZ

Nonstop1h 41mUnited Airlines

Deal found 1/12

$233

Tue 2/1811:20 amYTZ - MDW

Nonstop1h 50mPorter Airlines

Fri 2/211:05 pmMDW - YTZ

Nonstop1h 42mPorter Airlines

Deal found 1/12

$234

Sat 2/110:25 amYTZ - ORD

1 stop5h 20mAir Canada

Mon 2/31:55 pmORD - YTZ

1 stop5h 48mAir Canada

Deal found 1/11

$237

Tue 2/47:05 amYYZ - ORD

1 stop14h 08mMultiple Airlines

Thu 2/66:55 amORD - YYZ

1 stop16h 00mMultiple Airlines

Deal found 1/12

$243

Thu 2/611:20 amYTZ - MDW

Nonstop1h 50mAir Transat

Sun 2/91:05 pmMDW - YTZ

Nonstop1h 42mAir Transat

Deal found 1/12

$246

Thu 2/63:30 pmYYZ - ORD

Nonstop2h 11mLufthansa

Sun 2/96:28 pmORD - YYZ

Nonstop1h 57mLufthansa

Deal found 1/12

$251

Thu 2/66:30 amYYZ - MDW

1 stop7h 12mDelta

Sun 2/95:05 pmMDW - YYZ

1 stop4h 44mDelta

Deal found 1/13

$263

Thu 2/136:00 amYYZ - ORD

1 stop5h 38mAmerican Airlines

Wed 2/198:11 amORD - YYZ

Nonstop1h 40mAmerican Airlines

Deal found 1/12

$279

Mon 2/246:30 amYYZ - MDW

1 stop7h 12mWestJet

Wed 2/2610:19 amMDW - YYZ

2 stops12h 14mWestJet

Deal found 1/11

$293

Thu 2/66:40 pmYYZ - ORD

Nonstop1h 57mAir Canada

Sun 2/911:35 amORD - YYZ

1 stop6h 00mAir Canada

Deal found 1/12

$238

Tue 2/112:00 pmYTZ - ORD

2 stops17h 07mMultiple Airlines

Tue 2/187:51 pmORD - YTZ

2 stops22h 02mMultiple Airlines

Deal found 1/12

$277

Fri 2/142:45 pmYYZ - ORD

1 stop8h 13mDelta

Mon 2/176:59 amORD - YYZ

1 stop3h 57mDelta

Deal found 1/13

$290

Last-minute flights from Toronto to Chicago
Discover last-minute flight deals from Toronto to Chicago. Data last updated January 13, 2025 and is based on user searches.

Sun 1/199:00 pmYYZ - ORD

Nonstop2h 13mUnited Airlines

Tue 1/284:51 pmORD - YYZ

Nonstop1h 54mUnited Airlines

Deal found 1/12

$345

Sun 1/197:40 amYYZ - MDW

1 stop8h 41mMultiple Airlines

Tue 1/285:31 pmMDW - YYZ

2 stops28h 02mMultiple Airlines

Deal found 1/12

$385

Mon 1/206:30 amYYZ - ORD

1 stop16h 28mWestJet

Fri 1/312:35 pmORD - YYZ

1 stop7h 20mWestJet

Deal found 1/12

$376

Mon 1/2011:31 amYYZ - ORD

Nonstop2h 00mAmerican Airlines

Sun 1/2611:53 amORD - YYZ

1 stop4h 31mAmerican Airlines

Deal found 1/13

$377

Wed 1/227:50 pmYYZ - ORD

1 stop14h 49mMultiple Airlines

Sat 1/255:35 amORD - YYZ

1 stop17h 24mMultiple Airlines

Deal found 1/11

$262

Wed 1/2211:20 amYTZ - MDW

Nonstop1h 50mPorter Airlines

Sat 1/251:05 pmMDW - YTZ

Nonstop1h 42mPorter Airlines

Deal found 1/11

$276

Wed 1/221:05 pmYTZ - ORD

3 stops22h 12mMultiple Airlines

Sat 1/255:35 amORD - YTZ

2 stops11h 23mMultiple Airlines

Deal found 1/11

$302

Wed 1/227:45 amYYZ - MDW

1 stop6h 23mDelta

Sun 1/269:34 amMDW - YYZ

1 stop5h 38mDelta

Deal found 1/12

$331

Wed 1/226:30 amYYZ - MDW

1 stop12h 17mWestJet

Sat 1/256:59 pmMDW - YYZ

1 stop17h 49mWestJet

Deal found 1/11

$359

Wed 1/227:45 amYYZ - ORD

1 stop6h 10mDelta

Thu 1/231:40 pmORD - YYZ

1 stop4h 29mDelta

Deal found 1/13

$383

Thu 1/2310:25 amYTZ - ORD

1 stop5h 20mAir Canada

Sun 1/263:35 pmORD - YTZ

1 stop5h 15mAir Canada

Deal found 1/12

$310

Thu 1/239:00 amYYZ - ORD

1 stop6h 45mAir Canada

Sun 1/264:51 pmORD - YYZ

Nonstop1h 54mAir Canada

Deal found 1/12

$311

One-way flights from Toronto to Chicago
Search for one-way flight options from Toronto to Chicago. Find affordable one-way fares based on user searches. Data last updated January 13, 2025.

Tue 2/117:05 amYYZ - ORD

1 stop17h 27mMultiple Airlines

Deal found 1/11

$140

Wed 2/1210:25 amYTZ - ORD

1 stop5h 20mAir Canada

Deal found 1/13

$140

Wed 2/129:00 amYYZ - ORD

Nonstop2h 10mUnited Airlines

Deal found 1/13

$141

Fri 3/143:50 pmYTZ - MDW

Nonstop1h 50mPorter Airlines

Deal found 1/12

$141

Thu 2/611:20 amYTZ - MDW

Nonstop1h 50mAir Transat

Deal found 1/13

$143

Wed 2/1210:00 amYYZ - ORD

1 stop5h 45mAir Canada

Deal found 1/12

$146

Tue 2/42:00 pmYTZ - ORD

2 stops16h 31mMultiple Airlines

Deal found 1/13

$147

Mon 2/36:20 pmYYZ - ORD

Nonstop2h 00mAmerican Airlines

Deal found 1/12

$153

Sun 2/29:00 amYYZ - ORD

Nonstop2h 10mLufthansa

Deal found 1/12

$154

Mon 2/37:00 amYYZ - MDW

2 stops9h 43mMultiple Airlines

Deal found 1/12

$154

Mon 2/101:20 pmYYZ - ORD

1 stop8h 55mDelta

Deal found 1/12

$156

Wed 2/126:30 amYYZ - MDW

1 stop7h 12mDelta

Deal found 1/13

$159

Find flights from Toronto to Chicago within your budget

Fly from

Fly to

Route

Depart

Return

Price

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 2/6

12:20 pm-1:11 pm

Nonstop1h 51m

Chicago O'Hare Intl

Thu 2/6

8:30 pm-11:11 pm

Nonstop1h 41m

$233

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 2/14

11:20 am-12:10 pm

Nonstop1h 50m

Chicago Midway

Mon 2/17

1:05 pm-3:47 pm

Nonstop1h 42m

$234

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Thu 2/6

10:25 am-2:45 pm

1 stop5h 20m

Chicago O'Hare Intl

Sun 2/9

11:35 am-5:50 pm

1 stop5h 15m

$237

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 2/6

2:00 pm-2:51 pm

Nonstop1h 51m

Chicago O'Hare Intl

Sun 2/9

11:35 am-6:35 pm

1 stop6h 00m

$238

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Mon 2/3

7:00 am-5:20 pm

1 stop11h 20m

Chicago O'Hare Intl

Thu 2/6

6:55 am-11:55 pm

1 stop16h 00m

$247

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 2/6

11:20 am-12:10 pm

Nonstop1h 50m

Chicago Midway

Sun 2/9

1:05 pm-3:47 pm

Nonstop1h 42m

$250

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 2/6

2:00 pm-2:51 pm

Nonstop1h 51m

Chicago O'Hare Intl

Sun 2/9

9:50 am-12:25 pm

Nonstop1h 35m

$254

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 2/6

6:00 am-9:16 am

1 stop4h 16m

Chicago O'Hare Intl

Sun 2/9

4:58 pm-10:49 pm

1 stop4h 51m

$263

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 2/6

7:45 am-1:05 pm

1 stop6h 20m

Chicago Midway

Sun 2/9

5:05 pm-10:49 pm

1 stop4h 44m

$263

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 2/25

6:20 pm-7:20 pm

Nonstop2h 00m

Chicago O'Hare Intl

Thu 2/27

6:15 am-1:00 pm

1 stop5h 45m

$274

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/11

Showing 1-10 of 37 results

$140+ Cheap flights from Toronto (YTO) to Chicago (CHI)

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 2/11. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Toronto to Chicago with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

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

Cheap flight deals from Toronto to Chicago

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Find flight deals from Toronto to Chicago

Cheapest flights from Toronto to ChicagoExplore the most affordable flight options available from Toronto to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 13, 2025.

Explore the most affordable flight options available from Toronto to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 13, 2025.

Find flights from Toronto to Chicago within your budget

Cheapest flights from Toronto to Chicago
Explore the most affordable flight options available from Toronto to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 13, 2025.