Flights from Windsor to Chicago

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Lowest fares from Windsor to Chicago 

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May 2026
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Jun 2026
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Jul 2026
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Displaying fares for May-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 Jul 01, 2026

    Starting from

    CAD202

    Seen: 2 minutes ago

    Toronto (YYZ)Calgary (YYC)One-way fare
    /
    Economy    		Depart Jun 19, 2026

    Starting from

    CAD141

    Seen: 1 minute ago

    Toronto (YTO)Vancouver (YVR)One-way fare
    /
    Economy    		Depart Jul 07, 2026

    Starting from

    CAD162

    Seen: 58 minutes ago

    Toronto (YTO)Halifax (YHZ)One-way fare
    /
    Economy    		Depart May 30, 2026

    Starting from

    CAD90

    Seen: 55 minutes ago

    Vancouver (YVR)Toronto (YYZ)One-way fare
    /
    Economy    		Depart Jul 07, 2026

    Starting from

    CAD183

    Seen: 44 minutes ago

    Toronto (YYZ)Halifax (YHZ)One-way fare
    /
    Economy    		Depart Jun 12, 2026

    Starting from

    CAD124

    Seen: 1 hour ago

    Ottawa (YOW)Halifax (YHZ)One-way fare
    /
    Economy    		Depart Jun 05, 2026

    Starting from

    CAD219

    Seen: 59 minutes ago

    Toronto (YTO)Calgary (YYC)One-way fare
    /
    Economy    		Depart May 26, 2026

    Starting from

    CAD163

    Seen: 24 minutes ago

    Ottawa (YOW)Vancouver (YVR)One-way fare
    /
    Economy    		Depart Jun 11, 2026

    Starting from

    CAD236

    Seen: 1 hour ago

    Toronto (YYZ)Las Vegas (LAS)One-way fare
    /
    Economy    		Depart Dec 03, 2026

    Starting from

    CAD232

    Seen: 1 day ago

    Vancouver (YVR)Toronto (YTO)One-way fare
    /
    Economy    		Depart Jul 03, 2026

    Starting from

    CAD183

    Seen: 1 hour ago

    Toronto (YYZ)Edmonton (YEG)One-way fare
    /
    Economy    		Depart May 29, 2026

    Starting from

    CAD204

    Seen: 1 hour ago

    Hamilton, CA (YHM)Halifax (YHZ)One-way fare
    /
    Economy    		Depart Jun 02, 2026

    Starting from

    CAD112

    Seen: 14 minutes ago

    Ottawa (YOW)Calgary (YYC)One-way fare
    /
    Economy    		Depart Jun 12, 2026

    Starting from

    CAD163

    Seen: 4 hours ago

    Edmonton (YEG)Toronto (YYZ)One-way fare
    /
    Economy    		Depart May 29, 2026

    Starting from

    CAD196

    Seen: 20 minutes ago

    Halifax (YHZ)Toronto (YTO)One-way fare
    /
    Economy    		Depart Jun 03, 2026

    Starting from

    CAD118

    Seen: 49 minutes ago

    Hamilton, CA (YHM)Vancouver (YVR)One-way fare
    /
    Economy    		Depart Jul 03, 2026

    Starting from

    CAD191

    Seen: 8 minutes ago

    Calgary (YYC)Toronto (YYZ)One-way fare
    /
    Economy    		Depart Jun 25, 2026

    Starting from

    CAD128

    Seen: 1 minute ago

    Halifax (YHZ)Ottawa (YOW)One-way fare
    /
    Economy    		Depart May 31, 2026

    Starting from

    CAD213

    Seen: 2 hours ago

    Halifax (YHZ)Toronto (YYZ)One-way fare
    /
    Economy    		Depart Jun 13, 2026

    Starting from

    CAD118

    Seen: 7 minutes ago

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