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Cheap Flights from Toronto to Chicago (YYZ-MDW)
Prices were available within the past 7 days and start at S$208 for one-way flights and S$351 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Sat, 18 Jan - Sun, 19 Jan
YYZ
Toronto
MDW
Chicago
S$351 Return, found 5 days ago
S$351
Return
found 5 days ago
Sat, 18 Jan - Sun, 19 Jan
YYZ
Toronto
MDW
Chicago
S$361 Return, found 5 days ago
S$361
Return
found 5 days ago
Mon, 16 Dec - Wed, 18 Dec
YYZ
Toronto
MDW
Chicago
S$425 Return, found 5 days ago
S$425
Return
found 5 days ago
Mon, 16 Dec - Mon, 16 Dec
YYZ
Toronto
MDW
Chicago
S$456 Return, found 5 days ago
S$456
Return
found 5 days ago
Mon, 16 Dec - Mon, 16 Dec
YYZ
Toronto
MDW
Chicago
S$504 Return, found 5 days ago
S$504
Return
found 5 days ago
Sat, 18 Jan - Sun, 19 Jan
YYZ
Toronto
MDW
Chicago
S$507 Return, found 5 days ago
S$507
Return
found 5 days ago
Mon, 17 Feb - Fri, 21 Feb
YYZ
Toronto
MDW
Chicago
S$513 Return, found 2 days ago
S$513
Return
found 2 days ago
Sat, 18 Jan - Sun, 19 Jan
YYZ
Toronto
MDW
Chicago
S$516 Return, found 5 days ago
S$516
Return
found 5 days ago
Sat, 7 Dec - Mon, 9 Dec
YYZ
Toronto
MDW
Chicago
S$520 Return, found 5 days ago
S$520
Return
found 5 days ago
Thu, 12 Dec - Fri, 13 Dec
YYZ
Toronto
MDW
Chicago
S$552 Return, found 5 days ago
S$552
Return
found 5 days ago
Origin airport | Pearson Intl. |
Destination airport | Midway Intl. |
Airlines serving | Delta |
Return price | S$351 |
Distance | 692 km |
Perfect flights from Toronto to Chicago
Your Journey from Toronto to Chicago
Start your unforgettable journey with Expedia. Our broad selection of flights from Toronto to Chicago caters to every travel need. Whether you're yearning for a romantic escape, a solo adventure, or a cultural immersion, we've got you covered.
Choosing Your Ideal Flight
With Expedia, you have access to a wide range of airlines, including Delta. Our selection of flights from Pearson Intl. to Midway Intl. caters to every traveler's requirements, ensuring your journey aligns with your schedule. With options from 20 airlines, you're bound to find the perfect flight.
Maximizing Value with Toronto to Chicago Flights
Experience the joy of finding cheap flights from Pearson Intl. to Midway Intl. that fit your budget. Keep an eye out for our special deals and discounts, and check our flexible one-way fares from S$208 and roundtrip prices from S$351*.
Pre-Flight Essentials
Ensure a smooth journey from Toronto to Chicago with Expedia. From information about check-in times and in-flight amenities to guidance on baggage policies, we provide all the essentials to prepare you for your flight.
Experience the Vibrant Chicago
Picture yourself stepping off the plane in Chicago and immersing yourself in the unique atmosphere of . From local markets to cultural festivals, each city offers its distinct charm. Make the most of your trip by exploring local attractions and indulging in the local cuisine. With Expedia, explore all this and more, tailored to your budget.
Added Convenience on Your Toronto to Chicago Flight
Traveling with Expedia is more than just a flight. We offer details about in-flight amenities, baggage policies, and more to ensure a smooth and hassle-free journey. Choose from our variety of airlines and embark on a memorable journey from Toronto to Chicago.
Beyond the Flight – Exploring Chicago
With Expedia, your adventure extends beyond the flight. Explore Chicago at your own pace by renting a car or booking a hotel. Discover hidden gems off the beaten path and create unforgettable memories.
Book Your Flight from Toronto to Chicago with Confidence
Planning your next great adventure is a breeze with Expedia. Our user-friendly platform, unbeatable prices, and round-the-clock customer support make your travel experience seamless and stress-free. Embark on your journey from Toronto to Chicago with confidence. Book your travel arrangements with Expedia today.
*Note: Prices may vary based on availability and are subject to change.
Frequently asked questions
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Chicago
S$343.00
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Ottawa to Vancouver (YOW - YVR)Newark Liberty Intl. Airport to Chicago (EWR - ORD)Seoul to Chicago (ICN - ORD)Ottawa to Toronto (YOW - YYZ)Los Angeles to Chicago (LAX - ORD)Singapore to Windsor (SIN - YQG)Singapore to Chicago (SIN - ORD)San Francisco to Chicago (SFO - ORD)Ottawa to Singapore (YOW - SIN)Singapore to Kingston (SIN - YGK)Montreal to Chicago (YUL - ORD)New York to Chicago (LGA - ORD)Yangon to Chicago (RGN - ORD)Toronto to Timmins (YYZ - YTS)Singapore to London (SIN - YXU)London to Toronto (YXU - YYZ)Vancouver to Ottawa (YVR - YOW)New York to Chicago (JFK - ORD)Singapore to Ottawa (SIN - YOW)New York to Ottawa (JFK - YOW)Singapore to Thunder Bay (SIN - YQT)Newark Liberty Intl. Airport to Ottawa (EWR - YOW)Timmins to Toronto (YTS - YYZ)Flights to Hometown
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