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From masquerade balls to costumed segway tours, we've got the inside scoop on how Chi-town celebrates this holiday.

Jennifer Billock
October 14, 2015

Halloween in the Windy City isn't a single-day event—the city celebrates all month. If you're looking for some festivities that are off the beaten path, check out these events across town.

1. A new one on the scene this year, The Halloween Gathering is a full day of events put on by the Cultural Mile Association that promotes the city's creative initiatives. Beyond an afternoon arts festival, the main event is a nighttime parade along Columbus Avenue on October 24.

2. Hell in a Handbag Productions brings out the camp for Scream, Queen, Scream!, a show exploring the horrors of office work, through October 31 at Mary's Attic in Andersonville.

3. Centralia: The Bloody Rock Musical, plays through November 21 at pH Comedy Theater. The horror musical is about the town in Pennsylvania that sits over a burning coal mine, and performances include "blood zone" seating that comes with a free poncho.

4. Craving some Game of Thrones this Halloween Eve? Put on a character costume and head to Duet Dance Studio for the Halloween Game of Thrones Tango Dance Party.

5. The vaunted Drake Hotel is offering Nightmare on Walton this month, a series of Halloween events including movie viewings, a Mad Hatter tea, the hotel's annual Masquerade Ball on October 30,and Monster Bash on October 31.

6. Don a costume and join Absolutely Chicago or Steve's Segway Tours for a haunted Halloween segway tour.

7. The call is coming from inside the house—and you can have a front row seat for the bloodbath. BABYSITTERMASSACRE '78: The Musical plays through October 31 at The Public House Theatre.

8. Dress up the dogs and head to the Botanic Garden for a Spooky Pooch Parade on Halloween day.

9. True crime buffs won't want to miss the Chicago History Museum's 'Dark Side of History' tours, which explore the city's longstanding dark underbelly.

10. Forget karaoke—compete in FitzGerald's Nightclub's Ghosts of Rock Stars Past Halloween Costume Party and Lip-Sync Battle on October 24.

11. The city's oldest surviving house, the Glessner House, hosts Shadows on the Street: Haunted Tours of Historic Prairie Avenue on October 30 and 31. Join them on Halloween at the Clarke House for the annual Edgar Allen Poe reading.

12. Every year, the Monster Dash draws crazy crowds who view—or run—this lakefront race on the 31st.

13. Costumes and crab? The Heroes and Villains Costume Brunch at Shaw's Crab House on Halloween morning is a can't-miss event.

14. Later that night, glitz, glamour, and guts will reign supreme at the Virgin Hotel's Undead Disco.

15. The Northalsted Street Halloween Parade is an annual favorite, with zombie Thriller dances and costumed freaks dancing up and down the street.

16. Join 3,000 strangers for the Haunted Halloween Ball at Congress Plaza Hotel, said to be one of the world's most haunted hotels.

17. The fifth floor of the Godfrey Hotel transforms into a haunted house this Halloween. Explore the rooms alone or invite a group of friends for a private ghost hunt.

18. Spend a Rocky Horror-themed holiday surrounded by antique surgical implements at the Creatures of the Night Party in the International Museum of Surgical Science.

19. You also have your pick among the ever-popular bar crawl: the Wrigleyville Halloween Crawl; A Nightmare on Hubbard Street: The 4th Annual River North Halloween Costume Bar Crawl; the Halloween Day Crawl; the Zombies vs. Vampires Halloween Pub Crawl; the Chicago Halloween Pub Crawl Weekend; and the Halloween Trolley Bar Crawl.

Jennifer Billock lives in Chicago and covers the city for Travel + Leisure

Visit T+L's Travel Guide: What to Do In Chicago for more Chicago inspiration.

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