Howl-O-Ween Canine Cruise

Where are the pet parents who count down to dressing up their dog every Halloween? This one’s for you! Our 2026 Howl-O-Ween Canine Cruise is back, setting sail the second and third weekends of October aboard First Lady. Bring your pup in costume (humans can join the fun too!) for a 90-minute river and lake cruise featuring lively city highlights from our tour guide, pumpkin-flavored dog treats, an

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Open House Chicago 2026Sat–Sun, Oct 17–18More than 200 sites across Chicago, Downtown, the Loop & West LoopFree public festivalOne Weekend Only

Bad Momz of Comedy at The Comedy BarSaturday, October 17, 2026, 12:00 PM–2:00 PMThe Comedy Bar, Downtown, the Loop & West Loop$25 – $35One Day Only

Ballet of Lights: Sleeping Beauty in a Sparkling ShowSaturday, October 17, 2026, 4:00 PM–8:30 PMHistoric Main Stage at Athenaeum CenterOne Day Only

Ben Schwartz & FriendsSaturday, October 17, 2026, 7:00 PM–10:00 PMThe Chicago Theatre, Downtown, the Loop & West LoopOne Day Only