1. Halloween Masquerade: Gilded: Hosted by Lyric Opera of Chicago, this classy gathering promises to make Halloween a glamorous night to remember. Guests are encouraged to come dressed in their most extravagant costumes and elaborate masks to properly celebrate the masquerade, with all event proceeds going to The Patrick G. and Shirley W. Ryan Opera Center. The soiree will include live music, hors d'oeuvres and a costume contest. VIP guests receive access to a hidden speakeasy on the American Airlines Mezzanine with an expansive view of the party below. Oct. 27, 8PM, VIP tickets $200, 20 N. Upper Wacker Dr.
2. Godfrey Haunted Hotel: Join the Godfrey Hotel in celebrating its third annual Halloween bash. Held on the rooftop lounge, guests can enjoy music and speciality potions such as the Dia de los Muertos margarita. Only the bravest of party-goers can explore the fifth floor and 20 haunted rooms, with different spooky spectacles behind every door. Oct. 28, 8PM, tickets from $20, 127 W. Huron St.
3. Haunted Halloween Ball: Known for being one of the most haunted hotels in the country, the Congress Plaza Hotel, along with some help from B96 Chicago, will host a night of thrills and chills at Chicago’s biggest costume party. The annual event will offer performances by renowned DJs and a killer costume contest—and maybe even a surprise appearance by Al Capone's ghost, who is known to roam the haunted halls. Oct. 28, 9PM, tickets from $20, 520 S. Michigan Ave.
4. A Twilight Zone: The Chicago Athletic Association Hotel has created an opening to a new dimension with its annual Halloween event. For those daring enough to attend, the hotel’s rooftop bar will feature a downtown dance party with a live DJ, along with an adventure through the spooky suites on the hotel’s thirteenth floor. Oct. 28, 9PM, tickets $75, 12 S. Michigan Ave.
5. LondonHouse Disco Halloween: Enjoy a blast to the past at LondonHouse Chicago’s exclusive disco-themed Halloween party. Dressed in their grooviest ‘70s attire, attendees can sip on specialty-themed cocktails like the “Witches Brew” while overlooking the city from the stunning tri-level rooftop bar. The best costume has the chance to win a weekend stay at the glitzy hotel. Oct. 28, 9PM, tickets $25, 85 E. Upper Wacker Dr.