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Cheap flights from Toronto to Chicago from £120

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 5/10. Fares are subject to change and may not be available on all flights or dates of travel.
YTO — CHI
17 Oct — 24 Oct1
1 adult
1 adult, Economy

Cheapflights Tip: The best prices from Toronto to Chicago are usually found in July or June, booked 68 days in advance, depart on a Thursday or Friday and return on a Thursday

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 17 September 2025.

Round-trip from

£169

One-way from

£120

Popular in

December

Cheapest in

July

Average price

£186

Good round-trip deal

£434 or less

Good one-way deal

£291 or less
30/10-6/11
  • 30/10-6/11
  • 2 total stops
  • 36h 54m total
  • Toronto to Chicago
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United Airlines
  • United Airlines
  • 5/10
  • Nonstop
  • 1h 58m total
  • Toronto to Chicago
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Highest demand for flights based on searches. 7% potential increase in price (£11 potential increase over avg. return price).
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Cheapest flight prices on average. 1% potential price decrease (£3 potential savings vs. average return price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Toronto (YTO) to Chicago (CHI).
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Price to beat on a one-way flight from Toronto (YTO) to Chicago (CHI).
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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 17 September 2025.

Thu 30/1007:00YYZ - ORD
1 stop10h 53mMultiple Airlines
Thu 6/1118:06ORD - YYZ
1 stop26h 01mMultiple Airlines
Deal found 15/9£169
Tue 30/906:30YYZ - ORD
1 stop12h 09mMultiple Airlines
Fri 17/1018:18ORD - YYZ
1 stop19h 07mMultiple Airlines
Deal found 16/9£191
Thu 30/1007:00YYZ - ORD
1 stop5h 18mAir Canada
Thu 6/1115:55ORD - YYZ
Nonstop1h 39mAir Canada
Deal found 15/9£195
Tue 23/907:45YYZ - ORD
1 stop12h 15mWestJet
Thu 25/907:10ORD - YYZ
1 stop7h 12mWestJet
Deal found 15/9£199
Sun 12/1006:15YYZ - ORD
1 stop4h 28mWestJet
Sat 18/1007:10ORD - YYZ
1 stop9h 09mWestJet
Deal found 16/9£201
Tue 14/1018:09YYZ - ORD
1 stop3h 14mWestJet
Fri 24/1007:10ORD - YYZ
1 stop3h 10mWestJet
Deal found 15/9£202
Sun 12/1009:00YYZ - ORD
Nonstop1h 55mUnited Airlines
Sat 18/1018:01ORD - YYZ
Nonstop1h 43mUnited Airlines
Deal found 15/9£202
Sun 12/1012:15YYZ - ORD
1 stop6h 59mWestJet
Mon 20/1007:10ORD - YYZ
1 stop9h 09mWestJet
Deal found 15/9£205
Fri 17/1006:15YYZ - ORD
1 stop5h 05mWestJet
Mon 27/1007:10ORD - YYZ
1 stop6h 35mWestJet
Deal found 16/9£206
Tue 21/1018:09YYZ - ORD
1 stop3h 14mWestJet
Mon 3/1110:30ORD - YYZ
1 stop3h 15mWestJet
Deal found 16/9£207
Fri 24/1007:00YYZ - ORD
Nonstop1h 58mUnited Airlines
Sun 2/1107:10ORD - YYZ
Nonstop1h 48mUnited Airlines
Deal found 15/9£208
Thu 30/1012:30YTZ - ORD
1 stop8h 30mAir Canada
Thu 6/1107:15ORD - YTZ
1 stop6h 40mAir Canada
Deal found 15/9£235

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 17 September 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

Sun 12/10

07:00-07:58

Nonstop1h 58m

Chicago O'Hare Intl

Fri 24/10

18:01-20:44

Nonstop1h 43m

£202

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 23/10

07:00-07:58

Nonstop1h 58m

Chicago O'Hare Intl

Sun 26/10

10:00-12:39

Nonstop1h 39m

£202

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 15/10

18:09-20:23

1 stop3h 14m

Chicago O'Hare Intl

Mon 20/10

18:59-08:55

1 stop12h 56m

£202

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sun 12/10

09:00-09:55

Nonstop1h 55m

Chicago O'Hare Intl

Sat 18/10

21:12-23:58

Nonstop1h 46m

£202

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 10/10

18:00-18:49

1 stop25h 49m

Chicago O'Hare Intl

Sun 12/10

18:59-08:55

1 stop12h 56m

£202

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 17/10

07:00-07:58

Nonstop1h 58m

Chicago O'Hare Intl

Sun 26/10

07:10-09:58

Nonstop1h 48m

£202

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sun 12/10

07:00-07:58

Nonstop1h 58m

Chicago O'Hare Intl

Sun 19/10

16:42-19:37

Nonstop1h 55m

£202

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 18/10

07:00-07:58

Nonstop1h 58m

Chicago O'Hare Intl

Sun 19/10

16:42-19:37

Nonstop1h 55m

£202

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 18/10

07:00-07:58

Nonstop1h 58m

Chicago O'Hare Intl

Fri 24/10

18:01-20:44

Nonstop1h 43m

£202

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 14/10

21:00-22:07

Nonstop2h 07m

Chicago O'Hare Intl

Wed 22/10

08:55-11:49

Nonstop1h 54m

£202

Flights are sorted by cheapest return flights first.

Deals found on 15/9

Showing 1-10 of 35 results
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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 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 12 September 2025.

Booking 68 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, January is the cheapest month in which you can book a flight from Toronto to Chicago (average of £595). Flying from Toronto to Chicago in July is currently the most expensive (average of £843). 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 17 September 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 58% versus a flight in the evening.

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 14 September 2025.

Travellers seeking maximum savings on their Toronto to Chicago flight should consider departing on Thursday mornings 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 17 September 2025.

The most flights from YTO to CHI are scheduled on a Monday (66 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (45 on average).

How much does it cost for a return flight from Toronto to Chicago?

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 1h 58m. United Airlines provides one of the quickest options available for as low as £202. 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 £135. Air Canada is 27% 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 Toronto Pearson Intl - Chicago O'Hare Intl, Toronto Island - Chicago O'Hare Intl or Hamilton - 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 (88%), Egyptair (85%) and Copa Airlines (85%).

  • What are the cheapest flights from Toronto to Chicago?

    Looking at all options, your cheapest flight can be booked for £226. While the most popular route (Toronto Pearson Intl - Chicago O'Hare Intl) can be booked for £205 on average, our data indicates £389 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, January is the cheapest month in which you can book a flight from Toronto to Chicago (average of £595). Flying from Toronto to Chicago in July is currently the most expensive (average of £843). 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

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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.
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 17 September 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest£135Average£185FlexibilityNo 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.

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