Near North Side Unique & Unusual Halloween Events 2026

20 unique & unusual Halloween events in Near North Side and nearby.

For those seeking chills and thrills this Halloween season, consider the Haunted Halloween Half Marathon & 5km, an active outdoor pursuit. Alternatively, immerse yourself in a more theatrical experience with Late Nite Catechism: Holy Ghost Bingo, offering indoor amusement. Many other local happenings await your exploration, from historical tours to creative workshops, catering to diverse interests.

All Unique & Unusual Halloween Events Around Near North Side

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Illustration of small costumed children and a witch on a sunny autumn lawn with pumpkins, hay bales and orange trees

Family-Friendly Fall Activities

1 of 45 Haunted Halsted Halloween Parade Chicago

Chicago's Halloween night parade featuring a costume contest with cash prizes.

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 Illustration of a Halloween party at dusk with a ghost above string lights, two witches by a table, and glowing pumpkins

Food, Drink, and Parties

1 of 42 Memento Mori Halloween Gala Chicago

Haunting Halloween fundraiser inside a historic medical museum mansion.

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 Illustration of a small haunted cottage with glowing windows, ghosts, pumpkins and a black cat under a big pale moon

Haunted Experiences

1 of 5 Halloween Bash Medinah

Features a pumpkin patch, haunted trail hayride, and fireside s'mores.

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 Illustration of a small ghost and a jack-o'-lantern performing on a stage with red curtains, watched by a crowd at dusk

Movies, Theater, and Entertainment

1 of 8 BITE! by AirOtic Soirée Chicago

Dark Halloween burlesque and contemporary circus spectacle featuring world-class aerialists.

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Frequently Asked Questions

How long do ghost tours and walking events in Near North Side typically last?

The standard is 90 minutes covering about a mile at a stop-and-story pace; extended versions run two-plus hours and add interior visits. The pace is slower than a normal walk but heavy on standing, which tires people more than distance does. Plan the parking meter and babysitter around a hard two hours, and take the pre-tour restroom stop seriously, since routes rarely include one.

Can kids come on ghost tours in Near North Side?

Family-friendly early tours, usually the 7 pm slot, keep stories spooky but not graphic and welcome ages 8-plus; late-night tours lean into murder and macabre detail and often set 13+ or 18+ minimums. Check the tour's stated age guidance and pick the early slot for first-timers. Ninety minutes of night walking is the real limit for younger kids, so check the route length.

How should we dress for October outdoor events in Near North Side?

October is the swing month: afternoon events can be warm while anything after sunset drops fast, so the answer is always layers, base, zip layer, packable shell, plus closed shoes for grass and gravel venues. Toss gloves and a beanie in the bag after mid-October for night tours and outdoor screenings. Check the hourly forecast at event time, not the daily high.

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