Top Chicago Halloween Activities and Events for 2019

halloween pumpkin

From Trader Joe’s fully stocked up on all things pumpkin to a viral rumor surfacing that White Claw would debut a “Pumpkin Spice” version of the popular canned drink, we have never been more ready for the Halloween season to arrive. Heron Agency, Chicago’s premiere public relations and social media agency, has rounded up the top places and events for you to visit and attend this year to celebrate this holiday including a futuristic party at the South Loop’s hottest rooftop bar and an “IT” themed pop-up bar in Lincoln Park. Now grab last year’s cat ears and start making your plans!

Get Caught “Clowning Around” at ROOF on the Wit

ROOF on theWit, Chicago’s original rooftop perfectly set 27 stories above it all in the heart of downtown at 201 N State St, is getting in the spooky spirit this Halloween season. Featuring back to back special events, Chicagoans will enjoy a Madonna Tribute Party this Saturday, October 19 during her exclusive weeklong concert at the Chicago Theatre, followed by A Funhouse Halloween Party on Saturday, October 26, where guests are highly encouraged to dress in theme or risk being fed to the lions. Doors for both events open at 9 p.m. Tickets can be purchased at and

Spend a Night in the Future at VU’s One Year Anniversary Party

VU Rooftop Bar, the South Loop’s very first rooftop bar, located at 133 E. Cermak Rd., is celebrating its one year anniversary, 22 stories above the city with a futuristic themed party just in time for the Halloween season on Thursday, October 24 from 6:00 p.m. to 9:00 p.m. Step into VU (without the DeLorean) and enter the world to come with VU’s intense décor that will have guests looking to the future. Tickets to this exclusive celebration are now available and include live music, a beauty station by &BlowDry, drink specials, hors d’ouvres created by Executive Chef Nolan Narut, and much more. Themed costumes are not mandatory, but highly encouraged. Tickets to this event may be purchased on Eventbrite.

Trade in Your Mask for a Mullet and Your Broomstick for a Boom Box at Casati’s

Casati’s, 444 W. Fullerton Parkway, the family owned, modern Italian restaurant in Lincoln Park, is bringing Halloween back to the 80’s this year with their Hallo’s Eve 80’s Throw Back Bash on Wednesday, October 30. From 9:30 p.m. – midnight, Casati’s DJ will be spinning 80’s music and guests are encouraged to attend in their best 80’s threads. In addition to serving a new seasonal menu, Casati’s will offer Halloween cocktails for just $10 during the party, including The Prince (vodka, St. Elder liquor, fresh lemon juice, and muddled blackberries), The Cindy Lauper (muddled strawberries, Chambord, and fizzy ginger ale, finished with a squeeze of a fresh lemon), and more. For more information, please visit

Enjoy a Spooky Flick Poolside with the Whole Family

In the spirit of Halloween, the InterContinental Chicago Magnificent Mile Hotel, located at 505 North Michigan Ave, is extending its Dive-In Movie Series throughout the month of October with kid-friendly movie selections inspired by the upcoming “spooky” holiday. Each Saturday night, now through October 26, guests can grab a bag of freshly popped popcorn and a complimentary inflatable floaty before enjoying a full-length feature film projected on the hotel’s 80-foot jumbo screen while relaxing in the property’s historic indoor pool. Featured films include Frankenweenie, Beetlejuice, Paranorman and Hocus Pocus. In addition to the movie, guests may order bites and beverages from the hotel’s new poolside menu. For more information, please visit

Visit a Fright-Filled Pop-Up at Replay Lincoln Park

Get ready to hang with Georgie and the “The Losers Club” gang just in time for Halloween with Replay Lincoln Park, Chicago’s favorite arcade bar, 2833 N. Sheffield Ave., and the bar’s newest pop-up: It, based on the popular Stephen King novel and horror films. Beginning Friday, October 11, Replay Lincoln Park will transform into the disquieting town of Derry, Maine, home of Pennywise the Clown, eponymous being who emerges from the sewer to scare all the children. The pop-up will feature custom artwork and several scary photo opportunities including the abandoned house near the train yard at 29 Neibolt Street, an 80s aesthetic area with Tube TVs and various knick-knacks, a funhouse and more. On top of this, there will also be specialty cocktails like The S.S. Georgie and A Pennywise Punch, plus several events including It trivia, a Derry Afternoon Day Party, various costume contests and karaoke. For more information,

Enjoy a Mysterious Performance at the Historic Mayslake Peabody Estate

To open its 24th season, First Folio Theatre will begin with the literary-inspired production SHERLOCK’S LAST CASE, by Charles Marowitz. A threat hangs over the world’s most famous detective as he faces an opponent he never expected. This thrilling adventure mixes suspense, humor, and breath-stopping surprises. Directed by Janice L. Blixt, SHERLOCK’S LAST CASE previews October 2-4, opens October 5 and runs through November 3, 2019. Tickets are on sale now and may be purchased by calling the box office at 630.986.8067 or online at

Drink, if you Dare, at the World’s Largest Rooftop in the World 

Offshore, recognized by The Guinness Book of World Records as the World’s Largest Rooftop Bar, sitting on the third floor of Navy Pier at 1000 East Grand, is bringing the screams this Halloween season by decking out their over 52,300 square foot space with spooky décor throughout, complemented with three frightening cocktails named Hocus Pocus, Trick & Treat, and the Corpse Reviver II, available the month of October only. For more information, please visit