Flights from Toronto to Chicago starting from CAD200*

Promo Code

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Lowest fares from Toronto to Chicago 

Mar 2026
FromCAD275*
Seen: 8 hours ago
Flight Type One Way/Economy
Apr 2026
FromCAD201*
Seen: 7 hours ago
Flight Type One Way/Economy
May 2026
FromCAD201*
Seen: 5 hours ago
Flight Type One Way/Economy
CAD206
CAD968
Displaying fares for March-2026
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    • RangeCAD206-CAD968

    *Fares displayed have been collected within the last 48hrs and may no longer be available at time of booking. Learn more about this offer. Additional baggage fees and charges for optional products and services may apply.

    Flights from Toronto to Chicago

    Great deals from Toronto to Chicago

    CAD
    FromToDatesFare TypePrice

    Toronto (YTZ)

    Chicago (MDW)

    Jun 07, 2026

    		One-way fare/Economy

    *Fares displayed have been collected within the last 48hrs and may no longer be available at time of booking. Learn more about this offer. Additional baggage fees and charges for optional products and services may apply.

    Related Links

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    CAD

    Toronto (YTZ)to

    Chicago (MDW)
    Depart Jun 02, 2026
    Starting from
    CAD201
    Seen: 5 hours ago
    One-way fare
    Economy

    Toronto (YTO)to

    Chicago (MDW)
    Depart Apr 20, 2026
    Starting from
    CAD201
    Seen: 4 hours ago
    One-way fare
    Economy

    Toronto (YTZ)to

    Chicago (ORD)
    Depart Sep 15, 2026
    Starting from
    CAD200
    Seen: 7 hours ago
    One-way fare
    Economy

    URL Parameter Context to Context - Mary

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    From
    To
    Fare Type
    Dates
    Price
    Toronto (YYZ)Vancouver (YVR)One-way fare
    /
    Economy    		Depart Apr 08, 2026

    Starting from

    CAD186

    Seen: 13 minutes ago

    Toronto (YYZ)Las Vegas (LAS)One-way fare
    /
    Economy    		Depart Apr 10, 2026

    Starting from

    CAD204

    Seen: 8 minutes ago

    Toronto (YTO)Vancouver (YVR)One-way fare
    /
    Economy    		Depart Apr 12, 2026

    Starting from

    CAD149

    Seen: 27 minutes ago

    Toronto (YYZ)Calgary (YYC)One-way fare
    /
    Economy    		Depart Apr 17, 2026

    Starting from

    CAD170

    Seen: 16 minutes ago

    Toronto (YYZ)Fort Lauderdale (FLL)One-way fare
    /
    Economy    		Depart Apr 20, 2026

    Starting from

    CAD213

    Seen: 25 minutes ago

    Vancouver (YVR)Toronto (YYZ)One-way fare
    /
    Economy    		Depart Apr 09, 2026

    Starting from

    CAD167

    Seen: 17 minutes ago

    Toronto (YTO)Halifax (YHZ)One-way fare
    /
    Economy    		Depart Apr 16, 2026

    Starting from

    CAD111

    Seen: 25 minutes ago

    Ottawa (YOW)Fort Lauderdale (FLL)One-way fare
    /
    Economy    		Depart Apr 14, 2026

    Starting from

    CAD229

    Seen: 29 minutes ago

    Ottawa (YOW)Orlando (MCO)One-way fare
    /
    Economy    		Depart Jun 08, 2026

    Starting from

    CAD224

    Seen: 11 hours ago

    Ottawa (YOW)Halifax (YHZ)One-way fare
    /
    Economy    		Depart Apr 14, 2026

    Starting from

    CAD228

    Seen: 26 minutes ago

    Halifax (YHZ)Toronto (YTO)One-way fare
    /
    Economy    		Depart Apr 24, 2026

    Starting from

    CAD118

    Seen: 25 minutes ago

    Toronto (YYZ)Halifax (YHZ)One-way fare
    /
    Economy    		Depart Apr 05, 2026

    Starting from

    CAD124

    Seen: 29 minutes ago

    Ottawa (YOW)Vancouver (YVR)One-way fare
    /
    Economy    		Depart Apr 13, 2026

    Starting from

    CAD230

    Seen: 25 minutes ago

    Toronto (YYZ)Orlando (MCO)One-way fare
    /
    Economy    		Depart Mar 27, 2026

    Starting from

    CAD214

    Seen: 2 minutes ago

    Hamilton, CA (YHM)Vancouver (YVR)One-way fare
    /
    Economy    		Depart Apr 15, 2026

    Starting from

    CAD149

    Seen: 26 minutes ago

    Ottawa (YOW)Calgary (YYC)One-way fare
    /
    Economy    		Depart May 21, 2026

    Starting from

    CAD173

    Seen: 16 minutes ago

    Halifax (YHZ)Orlando (MCO)One-way fare
    /
    Economy    		Depart Jun 15, 2026

    Starting from

    CAD219

    Seen: 1 day ago

    Toronto (YTO)Calgary (YYC)One-way fare
    /
    Economy    		Depart Apr 16, 2026

    Starting from

    CAD143

    Seen: 16 minutes ago

    Vancouver (YVR)Toronto (YTO)One-way fare
    /
    Economy    		Depart Apr 14, 2026

    Starting from

    CAD141

    Seen: 1 minutes ago

    Halifax (YHZ)Ottawa (YOW)One-way fare
    /
    Economy    		Depart Apr 21, 2026

    Starting from

    CAD222

    Seen: 26 minutes ago

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