Explore flight options from Toronto to Chicago with competitive pricing starting from $277.
Toronto
YTZ
→
Chicago
MDW
11/05/2025 – 11/12/2025
Cheap flight deals from Toronto to Chicago
Average price start from:
i
$206
Round-trip flights from Toronto to Chicago starting at $206. Book now for the best deals!
One-way from:
i
$133
One-way flights from Toronto to Chicago starting at $133. Great for flexible travel!
Cheapest day:
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Wednesday
Wednesday is the cheapest day to fly from Toronto to Chicago. Save more by booking on this day!
Cheapest In:
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$157
May 2025
May 2025 is the cheapest month to fly from Toronto to Chicago with prices starting at $157.
Find flight deals from Toronto to Chicago
Cheapest flights from Toronto to Chicago
ONEWAY FLIGHTS
LAST MINUTE
CHEAP FLIGHTS
BEST FLIGHTS
Explore the cheapest oneway flights from Toronto to Chicago spotted daily.
YTZ
Toronto
YTZ - Toronto • 2025-11-05 • 09:00
Unknown
60 min
MDW
Unknown City
$133
Non-stop • 60 min
YTZ
Toronto
YTZ - Toronto • 2025-11-05 • 09:00
Unknown
60 min
MDW
Unknown City
$134
Non-stop • 60 min
YTZ
Toronto
YTZ - Toronto • 2025-11-05 • 09:00
Unknown
60 min
ORD
Unknown City
$135
Non-stop • 60 min
YTZ
Toronto
YTZ - Toronto • 2025-11-05 • 09:00
Unknown
60 min
MDW
Unknown City
$142
Non-stop • 60 min
YTZ
Toronto
YTZ - Toronto • 2025-11-05 • 09:00
Unknown
60 min
ORD
Unknown City
$142
Non-stop • 60 min
Price Trends & Analysis
Monthly Price Trends
Best time to book flights from Toronto to Chicago is during April.
Weather & Climate Information
Temperature
Chicago experiences a humid continental climate, with cold winters averaging temperatures between 20°F to 30°F and warm summers ranging from 70°F to 85°F. The best times for comfortable travel are late spring (May) and early fall (September to October), when temperatures are mild and outdoor activities are most enjoyable.
Rainfall
The best time to visit Chicago is during late spring (May to early June) or early fall (September to October) when the weather is mild and pleasant. These seasons also feature vibrant local events, such as the Chicago Blues Festival in June and the Chicago Gourmet Festival in September, making for an enjoyable experience without the summer crowds.
Airlines at MDW
Book your journey from Toronto to Chicago with leading airlines including Porter Airlines, Air Canada, Air Transat. These carriers provide excellent connectivity and multiple daily options for convenient travel.
The typical flight time is about 10-15 hours, with most flights featuring one stopover for better pricing and route optimization. When traveling from Toronto to Chicago, these airlines ensure a smooth and comfortable experience with their modern fleet and professional service.
Places to Visit in Chicago
Chicago, the Windy City, enchants with its stunning skyline, vibrant arts scene, and rich history. Stroll along the iconic Navy Pier, marvel at the masterpieces in the Art Institute, and savor deep-dish pizza in the historic Pilsen neighborhood. Visitors will be captivated by the city's dynamic culture, from jazz and blues music to its remarkable architecture, offering an unforgettable blend of urban adventure and Midwestern charm.
About Chicago
Explore the wonders of Chicago on your journey from Toronto. This remarkable destination blends cultural treasures with modern amenities, creating an enriching travel experience. Consider visiting during off-peak seasons for better value and fewer crowds.
Airlines Flying from Toronto to Chicago
Book your journey from Toronto to Chicago with leading airlines including Porter Airlines, Air Canada, Air Transat. These carriers provide excellent connectivity and multiple daily options for convenient travel.
The typical flight time is about 10-15 hours, with most flights featuring one stopover for better pricing and route optimization. When traveling from Toronto to Chicago, these airlines ensure a smooth and comfortable experience with their modern fleet and professional service.
Hotels in Chicago
If you're traveling to Chicago and need convenient accommodations near MDW Airport, several excellent hotel options are available. These hotels near Chicago airport not only provide easy access for travelers but also ensure a comfortable experience. When planning your trip, be sure to check for shuttle services and book in advance for the best rates.
Hotel
Category: Standard
Comfortable accommodations with modern amenities.
Location: Near airport
Hotel ID:
About Chicago
Explore the wonders of Chicago on your journey from Toronto. This remarkable destination blends cultural treasures with modern amenities, creating an enriching travel experience. Consider visiting during off-peak seasons for better value and fewer crowds.
Places to Visit in Chicago
Chicago, the Windy City, enchants with its stunning skyline, vibrant arts scene, and rich history. Stroll along the iconic Navy Pier, marvel at the masterpieces in the Art Institute, and savor deep-dish pizza in the historic Pilsen neighborhood. Visitors will be captivated by the city's dynamic culture, from jazz and blues music to its remarkable architecture, offering an unforgettable blend of urban adventure and Midwestern charm.
Hotels in Chicago
If you're traveling to Chicago and need convenient accommodations near MDW Airport, several excellent hotel options are available. These hotels near Chicago airport not only provide easy access for travelers but also ensure a comfortable experience. When planning your trip, be sure to check for shuttle services and book in advance for the best rates.
Hotel
Category: Standard
Comfortable accommodations with modern amenities.
Location: Near airport
Hotel ID:
Airlines Flying from Toronto to Chicago
Book your journey from Toronto to Chicago with leading airlines including Porter Airlines, Air Canada, Air Transat. These carriers provide excellent connectivity and multiple daily options for convenient travel.
The typical flight time is about 10-15 hours, with most flights featuring one stopover for better pricing and route optimization. When traveling from Toronto to Chicago, these airlines ensure a smooth and comfortable experience with their modern fleet and professional service.
Frequently Asked Questions
What is the cheapest flight from Toronto to Chicago?
The cheapest fare is $133. For the best deals, consider booking during April and flying on Wednesday.
How long is the flight from Toronto to Chicago?
Average flight time is around 10-15 hours, depending on layovers and the chosen route. Most flights include one stopover for optimal pricing.
Which airlines fly from Toronto to Chicago?
Multiple airlines operate this route including Porter Airlines, Air Canada, Air Transat. Check current schedules and availability for the best options.
What is the best time to book flights?
Booking 2–3 months in advance usually gives the best prices. Consider flying during April for additional savings.
Are there hotels near MDW Airport?
Yes, several hotels are conveniently located near MDW Airport, including options with shuttle services for easy airport access.
What should I know about Chicago?
Chicago offers a perfect blend of culture, history, and modern attractions. The best time to visit is during pleasant weather months for optimal experiences.
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