
Popular airlines from Toronto Pearson Intl. Airport (YYZ) to Chicago
- WestJet
WestJet
- Delta
Delta
- American Airlines
American Airlines
- Air Canada
Air Canada
- United
United
- Plan, book, fly with confidence
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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.

Thu, 6 Nov. - Wed, 12 Nov.
YYZ
Toronto
ORD
Chicago
NZ$300 Return, found 6 days ago
NZ$300
Return
found 6 days ago

Thu, 6 Nov. - Wed, 12 Nov.
YYZ
Toronto
ORD
Chicago
NZ$309 Return, found 6 days ago
NZ$309
Return
found 6 days ago

Thu, 6 Nov. - Wed, 12 Nov.
YYZ
Toronto
ORD
Chicago
NZ$316 Return, found 6 days ago
NZ$316
Return
found 6 days ago

Thu, 30 Oct. - Sun, 2 Nov.
YYZ
Toronto
ORD
Chicago
NZ$321 Return, found 1 day ago
NZ$321
Return
found 1 day ago

Thu, 6 Nov. - Wed, 12 Nov.
YYZ
Toronto
ORD
Chicago
NZ$326 Return, found 6 days ago
NZ$326
Return
found 6 days ago

Thu, 6 Nov. - Wed, 12 Nov.
YYZ
Toronto
ORD
Chicago
NZ$329 Return, found 6 days ago
NZ$329
Return
found 6 days ago

Thu, 30 Oct. - Sun, 2 Nov.
YYZ
Toronto
ORD
Chicago
NZ$331 Return, found 1 day ago
NZ$331
Return
found 1 day ago

Thu, 30 Oct. - Sun, 2 Nov.
YYZ
Toronto
ORD
Chicago
NZ$331 Return, found 1 day ago
NZ$331
Return
found 1 day ago

Thu, 30 Oct. - Sun, 2 Nov.
YYZ
Toronto
ORD
Chicago
NZ$337 Return, found 1 day ago
NZ$337
Return
found 1 day ago

Fri, 26 Sep. - Sun, 28 Sep.
YYZ
Toronto
ORD
Chicago
NZ$405 Return, found 6 days ago
NZ$405
Return
found 6 days ago
Origin airport | Pearson Intl. |
Destination airport | O'Hare Intl. |
Return price | NZ$299 |
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$193 and roundtrip prices from NZ$300. 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.
Explore a world of travel with Expedia
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Top Routes from Toronto
- Toronto to Mexico City (YYZ - MEX)
- Toronto to Auckland (YYZ - AKL)
- Toronto to Los Angeles (YYZ - LAX)
- Toronto to Calgary (YYZ - YYC)
- Toronto to Brussels (YYZ - BRU)
- Toronto to New York (YYZ - LGA)
- Toronto to Delhi (YYZ - DEL)
- Toronto to Istanbul (YYZ - IST)
- Toronto to Vancouver (YYZ - YVR)
- Toronto to London (YYZ - LHR)
- Toronto to Ahmedabad (YYZ - AMD)
- Toronto to Islamabad (YYZ - ISB)
Top Routes to Chicago
- Auckland to Chicago (AKL - CHI)
- Vancouver to Chicago (YVR - CHI)
- Los Angeles to Chicago (QLA - CHI)
- Honolulu to Chicago (HNL - CHI)
- Washington to Chicago (WAS - CHI)
- New York to Chicago (NYC - CHI)
- London to Chicago (LON - CHI)
- San Francisco to Chicago (SFO - CHI)
- Christchurch to Chicago (CHC - CHI)
Top Flight Destinations
- Flights to Las Vegas
- Flights to New York
- Flights to Orlando
- Flights to Chicago
- Flights to San Diego
- Flights to Myrtle Beach
- Flights to Panama City Beach
- Flights to Destin
- Flights to Los Angeles
- Flights to Miami
- Flights to Boston
- Flights to Nashville
- Flights to Atlantic City
- Flights to Atlanta
- Flights to San Francisco
- Flights to Virginia Beach
- Flights to Seattle
- Flights to Houston
- Flights to Honolulu
- Flights to San Antonio
Chicago Flight Deals
Chicago
NZ$299.30
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.