C$ 167+ Cheap flights to Chicago
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 24/9. Fares are subject to change and may not be available on all flights or dates of travel.
Flights to Chicago in 2024
Find the latest flights to Chicago in 2024, with up-to-date prices and availability. In the last 7 days, Cheapflights users made a total of 562,069 searches and data was last updated on 11 September 2024.
Cheap flights to Chicago in September & October 2024
Discover affordable flights and deals to Chicago in September and October 2024. In the last 7 days, Cheapflights users made a total of 562,069 searches and data was last updated on 11 September 2024.
The below flights offer some of the lowest fares to Chicago in September and October 2024. Be sure to check back soon as deals update often.
Chicago 2024 flight deals
Explore flight deals for Chicago in 2024, offering the best prices and options to suit your preferences. In the last 7 days, Cheapflights users made a total of 562,069 searches and data were last updated on 11 September 2024.
Listed are some of the best fares we've found on flights departing to Chicago in 2024. If these deals don't appeal to you, be sure to come back soon for more options.
Flights to Chicago departing soon
Discover available last-minute flight options to Chicago, providing immediate availability and potentially lower prices. In the last 7 days, Cheapflights users made a total of 562,069 searches and data was last updated on 11 September 2024.
Browse some of the best deals on flights leaving last minute to Chicago. Tip: double check your flight details before making your reservation.
One-way flights to Chicago
Explore one-way flight options to Chicago for greater flexibility in your travel plans. Find up-to-date pricing and availability for one-way flights. In the last 7 days, Cheapflights users made a total of 562,069 searches and data was last updated on 11 September 2024.
Take a look at some of the one-way flights departing to Chicago in the near future. Reserve a round-trip flight to Chicago instead by utilizing the search form above.
Direct flights to Chicago
Find flights to Chicago within your budget
Locate flights to Chicago that fit your budget, with regularly updated fares and availability. In the last 7 days, Cheapflights users made a total of 562,069 searches and data was last updated on 11 September 2024.
Fly from
Budget
C$ 278 - C$ 406
Route
Depart
Return
Price
Toronto IslandChicago Midway
YTZ - MDW
YTZMDW
Toronto Island
Thu 17/10
Nonstop1h 47m
Chicago Midway
Sun 20/10
Nonstop1h 39m
Toronto Pearson IntlChicago O'Hare Intl
YYZ - ORD
YYZORD
Toronto Pearson Intl
Wed 9/10
Nonstop1h 53m
Chicago O'Hare Intl
Sat 12/10
Nonstop1h 32m
Toronto Pearson IntlChicago O'Hare Intl
YYZ - ORD
YYZORD
Toronto Pearson Intl
Mon 28/10
Nonstop1h 57m
Chicago O'Hare Intl
Wed 30/10
Nonstop1h 41m
Toronto IslandChicago O'Hare Intl
YTZ - ORD
YTZORD
Toronto Island
Sat 5/10
1 stop5h 45m
Chicago O'Hare Intl
Sat 12/10
1 stop4h 54m
Toronto IslandChicago Midway
YTZ - MDW
YTZMDW
Toronto Island
Mon 28/10
Nonstop1h 50m
Chicago Midway
Tue 29/10
Nonstop1h 42m
Toronto Pearson IntlChicago O'Hare Intl
YYZ - ORD
YYZORD
Toronto Pearson Intl
Thu 3/10
1 stop5h 42m
Chicago O'Hare Intl
Sun 6/10
1 stop4h 50m
Toronto Pearson IntlChicago O'Hare Intl
YYZ - ORD
YYZORD
Toronto Pearson Intl
Sat 28/9
1 stop4h 31m
Chicago O'Hare Intl
Sun 29/9
Nonstop1h 32m
Toronto Pearson IntlChicago O'Hare Intl
YYZ - ORD
YYZORD
Toronto Pearson Intl
Sat 16/11
1 stop9h 13m
Chicago O'Hare Intl
Mon 25/11
1 stop5h 04m
Toronto Pearson IntlChicago O'Hare Intl
YYZ - ORD
YYZORD
Toronto Pearson Intl
Sat 12/10
1 stop16h 24m
Chicago O'Hare Intl
Tue 15/10
1 stop21h 50m
Best time to book a flight to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago with our price prediction graph.
Travel insights for flights to Chicago
Get recent, data-driven insights about flights to Chicago including ideal travel times, pricing trends, and more.
When is the best time to book a flight 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 6 September 2024.
To ensure you get the cheapest price possible for a flight 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.
How long is the flight to Chicago?
On average, a flight from Toronto to Chicago takes 5 hours 25 minutes. Flights to Chicago from other popular cities in Canada will vary in length. Below are a few examples of popular routes and their flight times.
When is the cheapest time to fly 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.
Users looking for the lowest fares to Chicago should consider flying on Sunday mornings, when prices are typically cheapest. Budget-minded travellers will want to avoid Sunday evenings, when prices are usually at their highest.
Weekly flight availability to Chicago
The most flights from Toronto to Chicago are scheduled on a Wednesday (57 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (37 on average).
What are the most popular airlines that fly to Chicago?
The most popular airlines flying from Toronto to Chicago are Air Canada, United Airlines and Porter Airlines.
What are the cheapest airlines that fly to Chicago?
The cheapest airlines flying from Toronto to Chicago are Porter Airlines, Air Canada and United Airlines.
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 11 September 2024.
Get a feel of what it's like to fly with United Airlines, Delta and Air Canada to Chicago by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
Comfort
Overall
Boarding
Food
Crew
Reviews
One of the worst flights ever. I got to the airport early for my 6:48 pm flight and tried to get on the 4:30 ish flight. The gate agent was one of the worst customer service people in my 20 yrs of flying Delta. Very rude and wouldn’t even talk to me about riding standby. Then flight took off 3 hrs late and when Landed in Atlanta, the gate people wouldn’t even try to get me on the plane. It was still there but door was closed. For all of my almost 2 million miles, the worst experience from Delta. I am highly disappointed as it was not my fault I have to sleep in Atlanta and not Jacksonville Florida
Entertainment
Comfort
Overall
Boarding
Food
Crew
Reviews
One of the worst flights ever. I got to the airport early for my 6:48 pm flight and tried to get on the 4:30 ish flight. The gate agent was one of the worst customer service people in my 20 yrs of flying Delta. Very rude and wouldn’t even talk to me about riding standby. Then flight took off 3 hrs late and when Landed in Atlanta, the gate people wouldn’t even try to get me on the plane. It was still there but door was closed. For all of my almost 2 million miles, the worst experience from Delta. I am highly disappointed as it was not my fault I have to sleep in Atlanta and not Jacksonville Florida
Entertainment
Comfort
Overall
Boarding
Food
Crew
Reviews
One of the worst flights ever. I got to the airport early for my 6:48 pm flight and tried to get on the 4:30 ish flight. The gate agent was one of the worst customer service people in my 20 yrs of flying Delta. Very rude and wouldn’t even talk to me about riding standby. Then flight took off 3 hrs late and when Landed in Atlanta, the gate people wouldn’t even try to get me on the plane. It was still there but door was closed. For all of my almost 2 million miles, the worst experience from Delta. I am highly disappointed as it was not my fault I have to sleep in Atlanta and not Jacksonville Florida
Entertainment
Comfort
Overall
Boarding
Food
Crew
Reviews
One of the worst flights ever. I got to the airport early for my 6:48 pm flight and tried to get on the 4:30 ish flight. The gate agent was one of the worst customer service people in my 20 yrs of flying Delta. Very rude and wouldn’t even talk to me about riding standby. Then flight took off 3 hrs late and when Landed in Atlanta, the gate people wouldn’t even try to get me on the plane. It was still there but door was closed. For all of my almost 2 million miles, the worst experience from Delta. I am highly disappointed as it was not my fault I have to sleep in Atlanta and not Jacksonville Florida
Entertainment
Comfort
Overall
Boarding
Food
Crew
Reviews
One of the worst flights ever. I got to the airport early for my 6:48 pm flight and tried to get on the 4:30 ish flight. The gate agent was one of the worst customer service people in my 20 yrs of flying Delta. Very rude and wouldn’t even talk to me about riding standby. Then flight took off 3 hrs late and when Landed in Atlanta, the gate people wouldn’t even try to get me on the plane. It was still there but door was closed. For all of my almost 2 million miles, the worst experience from Delta. I am highly disappointed as it was not my fault I have to sleep in Atlanta and not Jacksonville Florida
Entertainment
Comfort
Overall
Boarding
Food
Crew
Reviews
One of the worst flights ever. I got to the airport early for my 6:48 pm flight and tried to get on the 4:30 ish flight. The gate agent was one of the worst customer service people in my 20 yrs of flying Delta. Very rude and wouldn’t even talk to me about riding standby. Then flight took off 3 hrs late and when Landed in Atlanta, the gate people wouldn’t even try to get me on the plane. It was still there but door was closed. For all of my almost 2 million miles, the worst experience from Delta. I am highly disappointed as it was not my fault I have to sleep in Atlanta and not Jacksonville Florida