Cheap flights to Canada from Chicago

Round trips from Chicago from $254. Cheapest dates, deal ratings and where to book.

• Edmonton: $254, 2026-11-23 to 2026-12-30
• Toronto: $313, 2026-10-30 to 2026-11-08
• Montréal: $350, 2026-10-19 to 2026-10-23
• Winnipeg: $498, 2026-11-02 to 2026-12-24
• Halifax: $529, 2026-11-07 to 2026-11-15

Nearby

• United States
• Bahamas
• Mexico
• Cuba
• Belize
• Jamaica
• Haiti
• Honduras