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Book Chicago tickets in October 2026

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All things to do in Chicago in October 2026

Showing 24 of 106 experiences in Chicago

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Chicago · October 2026

Chicago in October 2026

Crisp weather, Halloween tours at the Tower of London, and quieter attractions before the Christmas rush. 107 experiences in Chicago are confirmed bookable in October 2026 — book ahead for the best seats at West End theatre shows and flagship attractions.

Top picks for October 2026: The Art Institute of Chicago Tickets, Chicago River Architecture Cruise, and Navy Pier Centennial Wheel: Entry Ticket.

Average rating across these Chicago experiences sits at 2.9 stars.

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The Art Institute of Chicago Tickets, Chicago River Architecture Cruise, and Navy Pier Centennial Wheel: Entry Ticket lead the line-up. 107 experiences in total across West End theatre, attractions, tours and Thames cruises.

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