Flights from Toronto to Chicago starting from CAD201*

Promo Code

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Lowest fares from Toronto to Chicago 

May 2026
FromCAD201*
Seen: 16 hours ago
Flight Type One Way/Economy
Jun 2026
FromCAD201*
Seen: 16 hours ago
Flight Type One Way/Economy
Jul 2026
FromCAD217*
Seen: 3 hours ago
Flight Type One Way/Economy
cmp-daily-histogram-bars-legend-min-price-aria-label CAD201
cmp-daily-histogram-bars-legend-max-price-aria-label CAD517
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    • RangeCAD201-CAD517

    *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 23, 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: 16 hours ago
    One-way fare
    Economy

    Toronto (YTO)to

    Chicago (MDW)
    Depart May 23, 2026
    Starting from
    CAD202
    Seen: 1 day ago
    One-way fare
    Economy

    Toronto (YTZ)to

    Chicago (ORD)
    Depart Sep 08, 2026
    Starting from
    CAD206
    Seen: 18 hours ago
    One-way fare
    Economy

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    From
    To
    Fare Type
    Dates
    Price
    Toronto (YYZ)Vancouver (YVR)One-way fare
    /
    Economy    		Depart Jul 02, 2026

    Starting from

    CAD214

    Seen: 2 minutes ago

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

    Starting from

    CAD141

    Seen: 7 minutes ago

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

    Starting from

    CAD162

    Seen: 1 hour ago

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

    Starting from

    CAD90

    Seen: 1 hour ago

    Vancouver (YVR)Toronto (YYZ)One-way fare
    /
    Economy    		Depart Jul 08, 2026

    Starting from

    CAD183

    Seen: 50 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: 1 hour ago

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

    Starting from

    CAD163

    Seen: 30 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: 4 minutes ago

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

    Starting from

    CAD112

    Seen: 20 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: 26 minutes ago

    Halifax (YHZ)Toronto (YTO)One-way fare
    /
    Economy    		Depart Sep 21, 2026

    Starting from

    CAD105

    Seen: 4 minutes ago

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

    Starting from

    CAD191

    Seen: 4 minutes ago

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

    Starting from

    CAD128

    Seen: 7 minutes 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 15, 2026

    Starting from

    CAD118

    Seen: 13 minutes ago

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