Flights from Windsor to Chicago

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Lowest fares from Windsor to Chicago 

Try updating your route (origin and/or destination) or interact with individual dates below in order to find offers.
Mar 2026
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Apr 2026
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May 2026
No fares searched this month
Displaying fares for March-2026
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    • Flights from Windsor to Chicago

    Great deals from Windsor to Chicago

    CAD

    There are no flight results that match your filtered criteria. Please adjust your search criteria.

    *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.

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    From
    To
    Fare Type
    Dates
    Price
    Toronto (YYZ)Vancouver (YVR)One-way fare
    /
    Economy    		Depart Apr 25, 2026

    Starting from

    CAD186

    Seen: 2 minutes ago

    Toronto (YYZ)Las Vegas (LAS)One-way fare
    /
    Economy    		Depart Jun 08, 2026

    Starting from

    CAD204

    Seen: 3 hours ago

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

    Starting from

    CAD158

    Seen: 32 minutes ago

    Toronto (YYZ)Calgary (YYC)One-way fare
    /
    Economy    		Depart Apr 10, 2026

    Starting from

    CAD170

    Seen: 25 minutes ago

    Toronto (YYZ)Fort Lauderdale (FLL)One-way fare
    /
    Economy    		Depart Apr 26, 2026

    Starting from

    CAD213

    Seen: 1 hour ago

    Vancouver (YVR)Toronto (YYZ)One-way fare
    /
    Economy    		Depart Apr 13, 2026

    Starting from

    CAD167

    Seen: 20 minutes ago

    Toronto (YTO)Halifax (YHZ)One-way fare
    /
    Economy    		Depart Apr 25, 2026

    Starting from

    CAD111

    Seen: 2 minutes ago

    Ottawa (YOW)Fort Lauderdale (FLL)One-way fare
    /
    Economy    		Depart Apr 27, 2026

    Starting from

    CAD229

    Seen: 1 hour ago

    Ottawa (YOW)Orlando (MCO)One-way fare
    /
    Economy    		Depart May 11, 2026

    Starting from

    CAD190

    Seen: 1 minute ago

    Ottawa (YOW)Halifax (YHZ)One-way fare
    /
    Economy    		Depart Apr 11, 2026

    Starting from

    CAD228

    Seen: 1 hour ago

    Halifax (YHZ)Toronto (YTO)One-way fare
    /
    Economy    		Depart Apr 07, 2026

    Starting from

    CAD118

    Seen: 15 minutes ago

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

    Starting from

    CAD124

    Seen: 45 minutes ago

    Ottawa (YOW)Vancouver (YVR)One-way fare
    /
    Economy    		Depart Apr 08, 2026

    Starting from

    CAD176

    Seen: 7 minutes ago

    Toronto (YYZ)Orlando (MCO)One-way fare
    /
    Economy    		Depart Apr 07, 2026

    Starting from

    CAD214

    Seen: 1 hour ago

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

    Starting from

    CAD158

    Seen: 14 minutes ago

    Ottawa (YOW)Calgary (YYC)One-way fare
    /
    Economy    		Depart Jun 25, 2026

    Starting from

    CAD208

    Seen: 2 hours ago

    Halifax (YHZ)Orlando (MCO)One-way fare
    /
    Economy    		Depart Jun 08, 2026

    Starting from

    CAD220

    Seen: 1 day ago

    Toronto (YTO)Calgary (YYC)One-way fare
    /
    Economy    		Depart Apr 24, 2026

    Starting from

    CAD135

    Seen: 4 minutes ago

    Vancouver (YVR)Toronto (YTO)One-way fare
    /
    Economy    		Depart Apr 11, 2026

    Starting from

    CAD141

    Seen: 31 minutes ago

    Halifax (YHZ)Ottawa (YOW)One-way fare
    /
    Economy    		Depart Apr 30, 2026

    Starting from

    CAD222

    Seen: 20 minutes ago

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