Spooky Season

Halloween In Chicago

A weekend that will good-haunt your memories.


Chicago is the city where fall comes alive, Halloween is fall’s best day and we’re proud to be at the epicenter of all of it – from the brilliant changing colors outside the Drawing Room windows to our central location that makes everywhere in the city easy to access. Whether you stay or stop by, it’s a great starting point to squeeze the life out of one of the most spooky and fun times of the year.  

90’s Halloween Skate Night at OUR very own Stagg Court

Don your best ripped jeans, neon jackets and tracksuits and leave your Discman at home because the 90s tunes will be spinning when the skates hit our historic Stagg Court for some dizzying fun. 90s attire and Halloween costumes welcome – book your slot and learn more here. Don’t forget that terrycloth headband – it’s gonna get real.

Arts in the Dark Parade

Halloween is for artists and this is their parade. On Saturday October 29 at 6pm experiencing this spectacle is easy as the parade route starts right around the corner from us. Set up camp early on State Street at Lake, then watch as the parade proceeds South to Van Buren. Unique floats, spectacle puppets and creative performances from Chicago’s renowned (Joffrey Ballet, Lookingglass Theatre) and lesser known art scene will roll down the historic backdrop of State Street. Make sure to book yourself a pre or post-parade table at Cindy’s or stool at the Milk Room early as Downtown will be hopping that night. 

Music Box of Horrors

Scared stupid. Perhaps you like to take your fear sitting down? Well, it’s your lucky day as the historic Music Box Theatre is showing fright-tastic favorites for the entire month of October. Ranging from ‘refined to ridiculous,’ this curated collection of films in this already spooky setting will have you all up in your feelings – and not the good kind. Check out the schedule here

Black Lagoon

You’ll find treats for adults only at this new immersive, horror-themed cocktail pop-up bar in River West. It’s real halloween – all goth no plastic pumpkins. Started last year in Toronto, this concept has finally landed in Chicago and was the brain child of bartenders Erin Hayes and Kelsey Ramage so the drinks are A+ – no apple cidertini’s here. Try the Blood Rage which combines beet juice, falernum and mezcal for a smoky, blood red sipper.

Graceland Cemetery

If you like your dead people real and you want a major dose of Chicago history (and we know all Chicago Athletic Association fans love this storied city) go for a walk around Graceland Cemetery. Many of the movers and shakers who originally made this city a powerhouse are spending their eternal rest in this beautiful space that’s one of the oldest monumental cemeteries in the US. Daniel Burnham, Potter Palmer, Charles Wacker, George Pullman – you name it, they’re all here. Take a tour Saturday, the 30 at 1:30 or visit yourself – it’s open every day until 4pm.

Looking for a place to tuck in this spooky season? We’ve got you covered.