Cheap flights from Toronto to Chicago from C$ 188
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 29/4. Fares are subject to change and may not be available on all flights or dates of travel.
The best prices from Toronto to Chicago are usually found in April or March, booked 77 days in advance, depart on a Friday or Thursday 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 20 February 2025.
Round-trip from | C$ 290 |
---|---|
One-way from | C$ 188 |
Popular in | December |
Cheapest in | April |
Average price | C$ 405 |
Good round-trip deal | C$ 282 or less |
Good one-way deal | C$ 175 or less |
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 20 February 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 20 February 2025.
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 629,999 searches. Data last updated 20 February 2025.
Fly from
Fly to
Route
Depart
Return
Price
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Thu 20/3
3:50 p.m.-4:40 p.m.
Nonstop1h 50m
Chicago Midway
Mon 24/3
5:35 p.m.-8:17 p.m.
Nonstop1h 42m
TorontoChicago
YTZ - ORD
YTZORD
Toronto Island
Fri 30/5
7:25 a.m.-11:24 a.m.
1 stop4h 59m
Chicago O'Hare Intl
Mon 2/6
10:40 a.m.-5:50 p.m.
1 stop6h 10m
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Fri 6/6
7:00 a.m.-7:59 a.m.
Nonstop1h 59m
Chicago O'Hare Intl
Sun 8/6
10:40 a.m.-5:58 p.m.
1 stop6h 18m
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Sat 22/3
7:55 p.m.-8:35 a.m.
1 stop13h 40m
Chicago O'Hare Intl
Tue 25/3
6:25 p.m.-11:55 p.m.
2 stops28h 30m
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Mon 17/3
9:30 a.m.-10:20 a.m.
Nonstop1h 50m
Chicago Midway
Thu 20/3
5:35 p.m.-8:17 p.m.
Nonstop1h 42m
TorontoChicago
YYZ - MDW
YYZMDW
Toronto Pearson Intl
Sat 12/4
6:30 a.m.-6:33 p.m.
1 stop13h 03m
Chicago Midway
Sun 20/4
10:20 a.m.-11:34 a.m.
1 stop24h 14m
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Sun 4/5
8:15 a.m.-9:10 a.m.
Nonstop1h 55m
Chicago O'Hare Intl
Mon 5/5
1:00 p.m.-3:46 p.m.
Nonstop1h 46m
TorontoChicago
YYZ - MDW
YYZMDW
Toronto Pearson Intl
Thu 20/3
10:20 a.m.-12:36 p.m.
1 stop3h 16m
Chicago Midway
Mon 24/3
2:55 p.m.-10:38 p.m.
1 stop6h 43m
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Fri 18/4
9:45 a.m.-4:08 p.m.
1 stop7h 23m
Chicago O'Hare Intl
Sat 19/4
5:00 p.m.-10:55 p.m.
1 stop4h 55m
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Fri 18/4
9:30 a.m.-10:20 a.m.
Nonstop1h 50m
Chicago Midway
Sat 19/4
12:55 p.m.-3:37 p.m.
Nonstop1h 42m
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.
Travel insights for flights from Toronto to Chicago
Get recent, data-driven insights about flights from Toronto to Chicago including ideal travel times, pricing trends, and more.
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 14 February 2025.
To ensure you get the cheapest price possible for a flight from Toronto to Chicago, you should look to book at least 77 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, January is the cheapest month in which you can book a flight from Toronto to Chicago (average of C$ 261). Flying from Toronto to Chicago in March is currently the most expensive (average of C$ 355). 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 20 February 2025.
Unlike in the afternoon, when flights are generally more expensive, you can save up to 66% on flights from Toronto to Chicago by exploring options for tickets in the evening.
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 30 June 2024.
Travelers seeking maximum savings on their Toronto to Chicago flight should consider departing on Friday evenings when fares are most often at their lowest. Wednesday afternoons 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 20 February 2025.
The most flights from YTO to CHI are scheduled on a Thursday (55 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (40 on average).
Rainfall in Chicago by month
Plan your trip to Chicago by taking into account the average rainfall totals by month.
In terms of precipitation, rainfall in Chicago ranges from 43.0 - 125.0 mm per month. August is typically the wettest month, when rainfall can reach 125.0 mm. January is typically the driest time to visit Chicago when rainfall is around 43.0 mm.
Temperature in Chicago by month
Plan your trip to Chicago by taking into account the average temperature totals by month.
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 20 February 2025.
Get a feel of what it's like to fly with Delta, Porter Airlines and Air Transat 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.
Comfort
Food
Crew
Boarding
Entertainment
Overall
Reviews
Aaron,Oct 2024
TUS - LAX
Comfort
Food
Crew
Boarding
Entertainment
Overall
Reviews
Aaron,Oct 2024
TUS - LAX
Comfort
Food
Crew
Boarding
Entertainment
Overall
Reviews
Aaron,Oct 2024
TUS - LAX
Comfort
Food
Crew
Boarding
Entertainment
Overall
Reviews
Aaron,Oct 2024
TUS - LAX
Comfort
Food
Crew
Boarding
Entertainment
Overall
Reviews
Aaron,Oct 2024
TUS - LAX
Comfort
Food
Crew
Boarding
Entertainment
Overall
Reviews
Aaron,Oct 2024
TUS - LAX
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.
Browse thousands of different options on Cheapflights for your next trip
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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 20 February 2025.
Top 5 airlines flying from Toronto to Chicago
Discover the top 5 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 629,999 searches. Data last updated 20 February 2025.
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.
Fly with Cheapflights
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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.