Find flights
Deals
When to book
Airlines
FAQs

Cheap flights from Toronto to Chicago from £98

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 6/2. Fares are subject to change and may not be available on all flights or dates of travel.
YTO — CHI
7 Dec — 14 Dec1
1 adult
1 adult, Economy, 0 bags

Cheapflights Tip: The best prices from Toronto to Chicago are usually found in July or June, booked 77 days in advance, depart on a Friday or Thursday and return on a Monday

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 7 November 2025.

Round-trip from

£147

One-way from

£98

Popular in

October

Cheapest in

July

Average price

£221

Good round-trip deal

£502 or less

Good one-way deal

£76 or less
Air Canada
  • Air Canada
  • 13/2-22/2
  • 1 total stop
  • 11h 37m total
  • Toronto to Chicago
Search Deals
Delta
  • Delta
  • 6/2
  • 1 total stop
  • 7h 35m total
  • Toronto to Chicago
Search Deals
Highest demand for flights based on searches. 4% potential increase in price (£7 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (£3 potential savings vs. average return price).
Search Deals
Average for round-trip flights in November 2025
Search Deals
Price to beat on a round-trip flight from Toronto (YTO) to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Toronto (YTO) to Chicago (CHI).
Search Deals

Find flight deals from Toronto to Chicago

Enter your travel dates to find the best prices.

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 7 November 2025.

Wed 26/1117:30YYZ - ORD
Nonstop2h 09mUnited Airlines
Sun 30/1113:19ORD - YYZ
Nonstop1h 43mUnited Airlines
Deal found 7/11£153
Sat 6/1209:00YYZ - ORD
Nonstop2h 02mUnited Airlines
Sun 7/1207:10ORD - YYZ
Nonstop1h 48mUnited Airlines
Deal found 5/11£154
Tue 18/1121:00YYZ - ORD
Nonstop2h 05mMultiple Airlines
Tue 25/1114:00ORD - YYZ
Nonstop1h 39mMultiple Airlines
Deal found 4/11£154
Thu 25/1217:30YYZ - ORD
Nonstop2h 20mMultiple Airlines
Tue 6/120:30ORD - YYZ
Nonstop1h 39mMultiple Airlines
Deal found 5/11£157
Wed 24/1221:00YYZ - ORD
Nonstop2h 05mUnited Airlines
Thu 8/116:50ORD - YYZ
Nonstop1h 55mUnited Airlines
Deal found 5/11£157
Tue 18/1117:30YYZ - ORD
Nonstop2h 09mMultiple Airlines
Mon 24/1107:05ORD - YYZ
1 stop7h 29mMultiple Airlines
Deal found 4/11£158
Tue 2/1214:09YYZ - ORD
1 stop7h 29mDelta
Fri 5/1208:55ORD - YYZ
1 stop4h 53mDelta
Deal found 5/11£160
Sun 7/1209:52YYZ - ORD
1 stop7h 30mDelta
Thu 11/1206:45ORD - YYZ
1 stop7h 03mDelta
Deal found 5/11£160
Wed 24/1219:40YYZ - ORD
1 stop5h 04mUnited Airlines
Wed 7/118:28ORD - YYZ
Nonstop1h 53mUnited Airlines
Deal found 5/11£161
Fri 21/1114:45YYZ - ORD
1 stop9h 58mMultiple Airlines
Sat 22/1107:05ORD - YYZ
1 stop7h 29mMultiple Airlines
Deal found 5/11£165
Tue 18/1119:40YYZ - ORD
1 stop5h 03mUnited Airlines
Mon 24/1121:20ORD - YYZ
Nonstop1h 39mUnited Airlines
Deal found 4/11£166
Mon 8/1208:50YTZ - ORD
1 stop5h 01mAir Canada
Thu 11/1213:59ORD - YTZ
1 stop6h 29mAir Canada
Deal found 5/11£265

Cheapflights Fare Finder

 
Customise 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 858,174 searches. Data last updated 7 November 2025.
Use the filters below to find and compare flights from Toronto to Chicago that are best for you.

Fly from

Toronto

Fly to

Chicago

Route

Depart

Return

Price

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 28/11

11:00-12:05

Nonstop2h 05m

Chicago O'Hare Intl

Sun 30/11

21:20-23:59

Nonstop1h 39m

£154

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 26/11

15:30-16:52

Nonstop2h 22m

Chicago O'Hare Intl

Sun 30/11

08:00-10:40

Nonstop1h 40m

£154

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 30/12

09:00-10:05

Nonstop2h 05m

Chicago O'Hare Intl

Thu 1/1

21:20-23:59

Nonstop1h 39m

£154

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 18/11

21:00-22:05

Nonstop2h 05m

Chicago O'Hare Intl

Tue 25/11

14:00-16:39

Nonstop1h 39m

£154

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 21/11

21:00-22:05

Nonstop2h 05m

Chicago O'Hare Intl

Sat 29/11

08:00-10:40

Nonstop1h 40m

£154

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Mon 29/12

21:00-22:05

Nonstop2h 05m

Chicago O'Hare Intl

Thu 1/1

21:20-23:59

Nonstop1h 39m

£154

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 25/12

17:30-18:50

Nonstop2h 20m

Chicago O'Hare Intl

Tue 6/1

20:30-23:09

Nonstop1h 39m

£157

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 15/1

12:10-17:21

1 stop6h 11m

Chicago O'Hare Intl

Sun 18/1

13:54-19:08

1 stop4h 14m

£160

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 1/4

17:10-21:56

1 stop5h 46m

Chicago O'Hare Intl

Sat 4/4

10:35-15:20

1 stop3h 45m

£160

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 27/11

06:05-08:57

1 stop3h 52m

Chicago O'Hare Intl

Tue 2/12

10:45-17:15

1 stop5h 30m

£160

Flights are sorted by cheapest return flights first.

Deals found on 5/11

Showing 1-10 of 30 results
1
2
3

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 return 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.

Cheapflights Insights

Everything you need to know about your flight from Toronto to Chicago

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

Use this chart to determine the optimal time to book a return flight from Toronto to Chicago. Price data was last updated on 31 October 2025.

Booking 77 days in advance of your planned departure date is, on average, the best time to get cheap flights from Toronto to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

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

Currently, June is the cheapest month in which you can book a flight from Toronto to Chicago (average of £63). Flying from Toronto to Chicago in February is currently the most expensive (average of £145). 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 time of day to fly from YTO to CHI?

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 7 November 2025.

When flying from Toronto to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight in the morning, which can drop the price by up to 53% versus a flight at midday.

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

Use this chart to determine the cheapest time to fly return from Toronto to Chicago. Price data was last updated on 2 November 2025.

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

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 7 November 2025.

The most flights from YTO to CHI are scheduled on a Monday (62 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (39 on average).

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 7 November 2025.
Get a feel of what it's like to fly with Porter Airlines from Toronto to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very Good
387 reviews
Check prices

Entertainment

7.0

Food

7.6

Boarding

8.2

Overall

8.0

Crew

8.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Kelly,Nov 2025

YVR - YUL

I recently flew with Porter Airlines on Flight PD372 on October 30th, and unfortunately, had a very disappointing experience. At the gate, one of their attendants gave me two boarding passes. I assumed these were for my itinerary from Vancouver to Montreal and back, but one of the boarding passes unexpectedly included a connecting flight to Toronto, which was never part of my booking or invoice. As a result of this error, my checked baggage was mistakenly routed to Toronto. When I contacted Porter’s customer service, I spoke to an agent who apologized on behalf of the attendant (employee number 13209961) and promised to have my luggage flown back to Montreal. However, shortly after, I was told there was nothing they could do except for me to travel to Toronto myself to pick up my bag. This is highly unreasonable and unfair, considering the issue was caused by their staff printing the wrong boarding pass. This entire situation caused me significant inconvenience and stress. I expected Porter to correct the mistake and deliver my luggage as originally planned, but instead, I was left with the burden of fixing an error that was not mine. I even have a photo of the staff badge of the employee who made the promise, yet the company still failed to honor it. I hope Porter Airlines reviews their internal communication and baggage handling procedures to prevent this from happening to other passengers. Customer care and responsibility fell short in this experience, and I am still waiting for a satisfactory resolution.
Porter Airlines
8.0
Very Good
387 reviews
Porter Airlines
8.0
Very Good
387 reviews
Check prices

Entertainment

7.0

Food

7.6

Boarding

8.2

Overall

8.0

Crew

8.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Kelly,Nov 2025

YVR - YUL

I recently flew with Porter Airlines on Flight PD372 on October 30th, and unfortunately, had a very disappointing experience. At the gate, one of their attendants gave me two boarding passes. I assumed these were for my itinerary from Vancouver to Montreal and back, but one of the boarding passes unexpectedly included a connecting flight to Toronto, which was never part of my booking or invoice. As a result of this error, my checked baggage was mistakenly routed to Toronto. When I contacted Porter’s customer service, I spoke to an agent who apologized on behalf of the attendant (employee number 13209961) and promised to have my luggage flown back to Montreal. However, shortly after, I was told there was nothing they could do except for me to travel to Toronto myself to pick up my bag. This is highly unreasonable and unfair, considering the issue was caused by their staff printing the wrong boarding pass. This entire situation caused me significant inconvenience and stress. I expected Porter to correct the mistake and deliver my luggage as originally planned, but instead, I was left with the burden of fixing an error that was not mine. I even have a photo of the staff badge of the employee who made the promise, yet the company still failed to honor it. I hope Porter Airlines reviews their internal communication and baggage handling procedures to prevent this from happening to other passengers. Customer care and responsibility fell short in this experience, and I am still waiting for a satisfactory resolution.

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 long is the flight from Toronto to Chicago?

    A quick flight from Toronto to Chicago can take about 2h 05m. United Airlines provides one of the quickest options available for as low as £154. Airlines will cover a distance of 436 mi. This flight may include one or multiple stops.

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

    Flying on Air Canada is currently your cheapest option to Chicago, with prices starting at £140. Air Canada is 28% cheaper than the average price of flights available within the next 90 days to this destination.

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

    Most travelers choose Hamilton - Chicago O'Hare Intl, Toronto Island - Chicago O'Hare Intl or Toronto Pearson Intl - Chicago O'Hare Intl when deciding on the best route from Toronto to Chicago.

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

    The top 3 most reliable airlines when flying from Toronto to Chicago are EVA Air (94%), Egyptair (92%) and ANA (88%).

  • What are the cheapest flights from Toronto to Chicago?

    Looking at all options, your cheapest flight can be booked for £76. While the most popular route (Hamilton - Chicago O'Hare Intl) can be booked for £457 on average, our data indicates £372 when flying from Toronto to Chicago.

  • 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 holiday 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.

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

    Currently, June is the cheapest month in which you can book a flight from Toronto to Chicago (average of £63). Flying from Toronto to Chicago in February is currently the most expensive (average of £145). 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.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Toronto to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Pearson Intl to O'Hare Intl flights

Top airline flying from Toronto to Chicago

Discover the top airline 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 858,174 searches. Data last updated 7 November 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest£140Average£175FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travellers 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 goes through 900+ travel sites to look for the best flight deals for flights from Toronto to Chicago. Too many options? Cheapflights also provides filters for things like airlines, price ranges, and number of stops to help you make a decision easily.

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

Cheapflights simply makes it quick and affordable to book flights from Toronto to Chicago by bringing together all flight options from hundreds of airlines and agencies online — and put it in one place for you to choose from. Plus, Cheapflights is 100% free to use for all.

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.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.