Chicagoans have a seemingly endless number of Halloween parties, parades, and events. One could go mad trying to navigate through all of the options. We want to make it easier for you. Here are some of our top picks for Halloween weekend in Chicago. Looking for a Haunted House? Check out our Essential Chicago Haunted House Guide.

Titanic Masquerade
Date: October 27
Time: 11 p.m.
Location: Spirit of Chicago

The producers of Pier Pressure will transform the Spirit of Chicago into a haunted Titanic. Dance the night away surrounded by the spirits of history’s most famous sunken unsinkable ship.

Hotel Masquerade: Gilded
Date: October 27
Time: 8 p.m.
Location: Lyric Opera House

Grab your most extravagant costume and indulge in the glitz and glamour of the Lyric Opera House. Proceeds support the emerging operatic talent of The Patrick G. and Shirley W. Ryan Opera Center.

Halloween Trolley Bar Crawl
Date: October 28
Time: 8 p.m.
Location: Multiple (it’ a bar crawl!)

One of the finest Halloween bar crawls is the Halloween Trolley Bar Crawl. Why is it one of the finest? Because you don’t need to spend all night walking. Slip into your costume, hop on the trolley, and drink at bars all around the city. Are you a UpOut Insider? Snag free tickets for your group of four here. That’s a value of $108 on us.

Haunted Halloween Ball
Date: October 28
Time: 9 p.m.
Location: Congress Plaza Hotel

The Congres Plaza Hotel is considered one of the most haunted places in the United State, so what better place to scare up some demons by dancing the night away?

Wrigleyville Halloween Crawl
Date: October 28
Time: 7 p.m.
Location: Wrigleyville

Start your Halloween weekend off with a costumed crawl through Wrigleyville. Tickets include a dinner buffet (you gotta eat!) and gift card to use at participating bars (which is pretty much all of them).

Saints and Sinners Halloween Party
Date: October 28
Time: 9 p.m.
Location: Lucky Strike, 322 E. Illinois Street

Lucky Strike hosts one of the biggest Halloween parties in the city with dancing, bottle service, bowling, and more.

Haunted Hotel Bash
Date: October 28
Time: 10 p.m.
Location: Hard Rock Hotel, 230 N. Michigan

The Hard Rock’s Haunted Hotel Bash features dancing, costumes, prizes, and if you want to stay the night, discounts on rooms.

Mad River Halloween Party
Date: October 28
Time: 9 p.m.
Location: Mad River Bar & Grille, 2909 North Sheffield

Mad River will turn into a creepy campout with staff dressed like Fairytale creatures and Princes or Princesses but with a scary, zombified or absolutely Mad twist. Guests are encouraged to embrace the theme (but not required).

Logan Square Halloween Parade
Date: October 29
Time 5 p.m.
Location: Palmer Square Park

The popular Logan Square Halloween Parade returns for year 14. The parade will be led straight down the boulevard by Mucca Pazza.

Day of the Dead Xiacgo
Date: October 29
Time: 3 p.m. to 8 p.m.
Location: National Museum of Mexican Art

The National Museum of Mexican Art is celebrating Día de los Muertos. The Harrison Park soccer field will be transformed for a Day of the Dead festival. The surrounding area will be turned into an elaborate work of art, featuring visual displays that reveal the story of the Day of the Dead. Families and individuals will create one of a kind ofrendas for their dearly departed loved ones.

Halloween at Navy Pier
Date: Multiple Dates
Time: Multiple Times
Location: Navy Pier

Navy Pier has Halloween activities scheduled right up until All Hallow’s Eve, but the big event is on October 28. The Aon Ballroom will be open from 8 p.m. to 2 a.m. for a massive Halloween dance party, Amazing Chicago’s Funhouse Maze will be overrun by terrifying clowns starting on October 26, and, of course, don’t miss the spectacular firework festivities.

 

 


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