Chicago Halloween Happenings | Downtown Chicago Hotels

Days are beginning to get shorter; temperatures are slowly dropping; the leaves will soon start to change colors.  All of this means one thing:  it’s time to start planning for Halloween!  Fortunately, Chicago never misses an opportunity to celebrate in style. 

Arts in the Dark Halloween Parade

Festivities will kick off on October 21st with a parade celebrating Halloween put together by members of the city’s outstanding creative community.  The parade will feature floats, live music, puppets, and more.  In previous years, the event has spotlighted institutions such as The Field Museum, the Chicago Symphony Orchestra, local improv groups, and even a Thriller flash mob.  The parade is a family-friendly affair that begins at dusk and will run from the intersection of Columbus and Balbo north to Monroe Street.  What better way to start off Halloween than with a free parade?

Most of the other festivities will occur on Saturday, October 28th.  Why not use the week leading up to that day to satisfy some last-minute costume shopping and load up on candy? 


Chicago Costume Company consistently ranks as one of the top costume stores in the city.  They have two locations, but the most accessible from Best Western River North is their store at 1120 West Fullerton.  Its location is a short walk west of the Fullerton red line station, which means you can catch the red line train at Grand going north toward Howard and depart just four stops later.  Other favorites include Hollywood Mirror near the red line’s Belmont stop and Fantasy Costumes, located on the city’s west side. 


If you need to load up on candy, downtown Chicago has got you covered.  The Ghirardelli Ice Cream and Chocolate Shop is located just blocks away at 830 N. Michigan, while candy super store Candyality is just across the street inside Water Tower Place.  Dylan’s Candy Bar is just south of Water Tower Place at 445 N. Michigan and features an impressive selection covering two floors of sweets.  Fannie May is just south of Dylan’s at 343 N. Michigan, and you can never go wrong with Garrett Popcorn, with a multitude of locations downtown, including one at Navy Pier.  And if you’re at Navy Pier on October 28th, you might as well stay put.

Navy PIer

Navy Pier will feature “Fright Flicks” on October 21st and October 28th at 4 p.m. and 6 p.m., respectively.  The Chicago landmark will host these Halloween-themed movies outdoors and free to the public.  Details on movie titles will be released via their website soon. Make sure to stick around till early evening, as they will also continue their Halloween fireworks show tradition, starting at about 9:30 pm.  Although details have not yet been released, Navy Pier will hold a number of other family-friendly events throughout the days leading up to Halloween, so be sure to check their website for more information.

For adults 21+, Navy Pier will throw a Haunted Halloween Ball in their Grand Ballroom starting at 8 pm, featuring DJs, dancing, and more.  Tickets are around $25, and they are limited, so don’t wait long if you’d like to include this in your weekend schedule.

Spooky Zoo Spectacular

Another favorite family-friendly event takes place starting at 10:00 am on Saturday, October 28th, lasting till 1:00 pm, at the Lincoln Park Zoo.  Named the Spooky Zoo Spectacular, this city tradition caters to families and children and will feature costumes, a haunted house, and an early opportunity for trick-or-treating.  This year’s Spooky Zoo Spectacular will be the 31st anniversary of this city favorite.  Do be aware that this event traditionally draws large crowds.

Chicago Humanities Festival

During the weekend of the 28th, the Chicago Humanities Festival will be featuring authors, public servants, and speakers presenting societal issues and discussing their work at various locations throughout the city, so do expect the weekend to be bustling with activity.

It will be an action-packed week in Chicago, so start picking out your favorite events and enjoy all the city has to offer.



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