
Popular airlines from Toronto Pearson Intl. Airport (YYZ) to Chicago
- Porter Airlines
Porter Airlines
- Delta
Delta
- WestJet
WestJet
- American Airlines
American Airlines
- Air Canada
Air Canada
- United
United
- Be in the knowGet alerts if flight prices drop or rise*
- Book smarterSave up to 35% on select hotels after you book a flight*
Cheap Flights from Toronto (YYZ) to Chicago (CHI)
Prices were available within the past 7 days for one-way flights and round trip tickets for the period specified. Prices and availability are subject to change. Additional terms apply.

Fri, 10 Apr - Fri, 17 Apr
YYZ
Toronto
ORD
Chicago
NZ$319 Return, found 6 days ago
NZ$319
Return
found 6 days ago

Mon, 13 Apr - Tue, 14 Apr
YYZ
Toronto
ORD
Chicago
NZ$329 Return, found 6 days ago
NZ$329
Return
found 6 days ago

Thu, 29 Jan - Sun, 1 Feb
YYZ
Toronto
ORD
Chicago
NZ$359 Return, found 5 hours ago
NZ$359
Return
found 5 hours ago

Thu, 29 Jan - Sun, 1 Feb
YYZ
Toronto
ORD
Chicago
NZ$364 Return, found 5 hours ago
NZ$364
Return
found 5 hours ago

Thu, 29 Jan - Sun, 1 Feb
YYZ
Toronto
ORD
Chicago
NZ$368 Return, found 5 hours ago
NZ$368
Return
found 5 hours ago

Thu, 29 Jan - Sun, 1 Feb
YYZ
Toronto
ORD
Chicago
NZ$379 Return, found 5 hours ago
NZ$379
Return
found 5 hours ago

Thu, 29 Jan - Sun, 1 Feb
YYZ
Toronto
ORD
Chicago
NZ$385 Return, found 5 hours ago
NZ$385
Return
found 5 hours ago

Thu, 29 Jan - Sun, 1 Feb
YYZ
Toronto
ORD
Chicago
NZ$387 Return, found 5 hours ago
NZ$387
Return
found 5 hours ago

Thu, 29 Jan - Sun, 1 Feb
YYZ
Toronto
ORD
Chicago
NZ$389 Return, found 5 hours ago
NZ$389
Return
found 5 hours ago

Mon, 13 Apr - Tue, 14 Apr
YYZ
Toronto
ORD
Chicago
NZ$390 Return, found 6 days ago
NZ$390
Return
found 6 days ago
Origin airport | Pearson Intl. |
|---|---|
Destination airport | O'Hare Intl. |
Return price | NZ$319 |
Distance | 697 km |
Perfect flights from Toronto to Chicago
Embark on an unforgettable journey without breaking the bank with Expedia's incredible deals on cheap flights from Toronto to Chicago. Whether you're aching for a romantic escape with your partner, craving an adventurous solo expedition, or yearning to immerse yourself in the local history and culture, we've got you covered.
Picture yourself strolling through the streets of , surrounded by breathtaking architecture and absorbing the vibrant atmosphere of this captivating city. Indulge in the mouth-watering local specialties, from tantalizing street food to exquisite fine dining. With Expedia, you can experience all of this and more, without sacrificing your budget.
Our flexible Pearson Intl. to CHI-All Airports ticket options cater to your travel preferences, with incredible one-way fares from NZ$204 and roundtrip prices from NZ$319. Whether you're planning a short city break or a longer adventure, our dynamic pricing ensures that you find the best deals for your journey.
But the magic doesn't stop there. Expedia offers a range of partner services to enhance your trip. Rent a car at CHI-All Airports and explore and its surrounding areas at your own pace. Discover hidden gems off the beaten path, and create unforgettable memories. We also provide a handpicked selection of accommodations, from charming bed and breakfasts to luxury hotels, ensuring that you have a comfortable and memorable stay.
Planning your next great adventure is a breeze with Expedia. Our user-friendly platform, unbeatable prices, and round-the-clock customer support are designed to make your travel experience seamless and stress-free. So, why wait? Book your to travel arrangements today and embark on the journey of a lifetime in Chicago.
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Top Routes from Toronto
- Toronto to Chicago (YYZ - ORD)
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- Toronto to Delhi (YYZ - DEL)
- Toronto to Manila (YYZ - MNL)
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Toronto Airports
Toronto
Expedia's Latest Trends
Flights
- Boston to Auckland (BOS - AKL)
- Toronto to New York (YYZ - NYC)
- Seattle to Auckland (SEA - AKL)
- Houston to Orlando (HOU - MCO)
- Auckland to Las Vegas (AKL - LAS)
- New York to Las Vegas (NYC - LAS)
- Boston to New York (BOS - JFK)
- Auckland to New York (AKL - NYC)
- Las Vegas to New York (LAS - JFK)
- Honolulu to Las Vegas (HNL - LAS)
- Las Vegas to Auckland (LAS - AKL)
- Auckland to Seattle (AKL - SEA)
- Auckland to Philadelphia (AKL - PHL)
- Christchurch to Las Vegas (CHC - LAS)
- London to New York (LON - NYC)
- Auckland to San Diego (AKL - SAN)
- New York to Los Angeles (NYC - LAX)
- San Francisco to Las Vegas (SFO - LAS)
- Houston to New Orleans (HOU - MSY)
- Las Vegas to San Francisco (LAS - SFO)
- Auckland to Cincinnati (AKL - CVG)
- Miami to New York (MIA - NYC)
- Los Angeles to San Diego (LAX - SAN)
- Auckland to Boston (AKL - BOS)
- Auckland to Ottawa (AKL - YOW)
- Las Vegas to Los Angeles (LAS - LAX)
- Vancouver to Seattle (YVR - SEA)
- Hamilton to Tauranga (YHM - TRG)
- Los Angeles to Las Vegas (LAX - LAS)
- Los Angeles to Seattle (LAX - SEA)
*Available to Expedia members.