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Celebrate Halloween in the Chicago Loop

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Posted  12 days ago  in  Loop List, Arts and Culture, Trending

2 MIN READ – Rather than being upset that another Chicago summer is over, prepare your favorite costume for a month of spooktacular Halloween festivities in the Chicago Loop. See our top picks for events, specials, and more below.


Arts in the Dark Parade

The 7th Arts in the Dark Halloween Parade will return to State Street on October 30 as the finale of the city's "Halloweek" program. This event has drawn together over 50,000 guests and participants for a magical evening parade that celebrates Halloween as the “artist’s holiday.” Past participants include world-renowned companies like the Joffrey Ballet, celebrated Chicago organizations like Lookingglass Theatre Company, important programs like After School Matters, and aspiring artists in every field. It is a dazzling event that delights the audience with unique floats, spectacle puppets, and creative performances – all set against the backdrop of historic State Street. Learn more about attending this free event here.10.19.19 Arts in the Dark 06 credit James Richard IV Photography

Chicago Loop Alliance Foundation’s Maskerade Gala

If you’d like a VIP viewing experience of the Arts in the Dark Parade and the opportunity to mingle with some of the Loop’s most influential movers and shakers, consider purchasing tickets to the Chicago Loop Alliance Foundation’s Maskerade Gala. The annual fundraiser takes place on October 30 at the Palmer House Hilton and will feature live entertainment, dancing, drinks, and bites. Your attendance supports the work of the Chicago Loop Alliance Foundation, including such fabulous public art projects and events as Sundays on State, the Loop Mural Walk, and more.

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Chicago Riverwalk

Celebrate Halloween on the Chicago Riverwalk with the Riverwalk Fall Festival now through October 31.   Get a passport from one of the participating vendors to get stamped throughout the month to win a Riverwalk goodie bag filled with treats. There are a ton of events to enjoy all month long! Bring your dog to The Northman for Puppyween Yappy Hour, an end-of-the-season costume party taking place on October 28. The Northman Pergola stage will also host a series of performances for Oktoberfest throughout the month. Or visit Island Party Hut’s pumpkin patch and take a floating hay ride out to the lakefront for a quick trip and amazing views of the Chicago skyline. And through mid-October, Chicago Electric Boat Company customers will captain their very own eco-friendly, fully enclosed boats along the Chicago River. Vendor specials, live music dates, and more details can be found here.

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Skydeck Chicago

Are you spooked by heights? Skydeck Chicago is both the highest observation deck in the U.S. at 1,353 feet and the city’s second most visited tourist destination. Visit Skydeck Chicago at Willis Tower in costume the week of Halloween (October 25-31) and receive a free 6x8” professional photo on The Ledge. Additionally, the first 100 visitors wearing a costume will receive a free donut at Do-Rite’s Willis Tower location. The revamped Skydeck Chicago opened on April 23 and provides a can’t-miss, one-stop attraction to discover and see all that the city of Chicago offers from an incomparable vantage point. The complete transformation encompasses the attraction’s lower level, delivering a brand-new interactive museum that celebrates the unique personality, history, neighborhoods, and sites of Chicago. The lower-level museum is further complemented by a visit to the internationally recognized observation deck to take in the city from 103 floors up and step out on The Ledge; the four thrilling glass floor balconies extending from the Tower. 

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Spooky Hours at Museum of Illusions

Something's brewing at the Museum of Illusions! Stop in for Spooky Hours every Thursday evening this October. The adults-only weekly event will feature exclusive after-hours access to the museum, a magician, and wine and beer provided by Left Coast. Events will take place every Thursday in October starting at 8 p.m. Tickets are available exclusively through Chicago Bucketlisters. As an added safety measure, all guests will be required to provide proof of vaccination for entry. Learn more here.

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American Writers Museum

The American Writers Museum rounded up some fun ways here for you to get into the spirit of the spooky season with horror writing, mystery and detective stories, Halloween reading, podcasts, and more. Discover more about Poe, Bradbury, and other writers of the past by carving out some time to visit the museum Thursday through Monday, 10 a.m. to 5 p.m.

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Halloween Brunch at Venteux

On Halloween from 10 a.m. to 3 p.m., eat, drink, and be scary! Come in costume to Venteux and enjoy complimentary bottomless mimosas and rose (with the purchase of an entrée and a 90-minute time limit) for their Halloween brunch. Learn more.

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Bar Allegro

The rhythm of The Allegro is the beat of Chicago itself – unique, exciting, and unmistakable – where timeless glamour meets a modern sophistication and classic elegance melds into a confident urban vibe. Visit Bar Allegro where they’re offering the Royal Pimm’s Cup this fall. The drink is inspired by the original Pimm’s Cup, which was enjoyed in the English countryside – with a Chicago twist! Bar Allegro’s Royal Pimm’s Cup has orange zest infused Pimm’s and banks rum, Demarara Lemon Juice, and Ginger Beer, delightfully garnished with an orange and brandied cherry flag. Perfectly festive!

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Sugar Bliss

We all love Halloween candy, but have you tried Sugar Bliss’ Candy Corn or Candy Bar Cupcakes, Mummy Brownies, Halloween Cookies, or Cake Pops? Sugar Bliss offers these Halloween treats and so much more, including cookie and cupcake decorating kits and Halloween sweets packages. Visit them at their retail location, 122 S. Wabash, or online for all their options!

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