The best things to do in Chicago this weekend

The Congress Plaza Hotel hosts its annual Haunted Halloween Ball, inviting costumed attendees to spend a night dancing and celebrating in a building that some claim is haunted. Guests will be able to mingle with spirits and the not-yet-deceased in the hotel's ballrooms, which sport spooky decorations, zombie cocktail servers, go-go dancers and vampire bellmen. You'll have access to multiple cash bars, great views of the city's skyline and the chance to enter a costume contest and compete for $2,000 in cash and prizes.

The Izakaya at Momotaro is back again with its annual Halloween party and this year, the space is transforming into a haunted cinema. Step into a world of spine-tingling vintage horror movies brimming with thrills while feasting on izakaya bites and an array of delicious desserts. The bar team is also creating a menu of special cocktails that pay homage to classic films. Tickets are $95 per person.

Have a witchy night in Pilsen at this booze crawl throughout the neighborhood, where attendees can sip samples of beer and cocktails from 10 local bars and restaurants while enjoying live music and DJ tunes. Proceeds go toward Pilsen Fest, the neighborhood's annual summer street festival.

The first annual Will Run For Beer comes to Lincoln Park. After completing a 5K along the Chicago lakefront, runners will celebrate with a brewfest featuring 22 beers, brats and pretzels, and live music. Tickets for just the brewfest are also available if you don’t feel like working up a sweat before drinking.

Join Absolutely Anything Essential for a family-friendly fall fest. The event will have a kids zone, live entertainment, local vendors selling fruits, veggies and wares, a costume contest and more. This is Life, NFP will also be providing free haircuts and coats for children (must register for a complimentary coat).

Chicago's most adorable Halloween party happens every year at the MCA Sculpture Garden, where local dog (or cat) owners bring their costumed pets for a parade around the premises. The best-dressed furry friend is chosen by Alderman Brian Hopkins and Maureen Schulman and will receive prizes, but rest assured that everyone is a wiener! 

I|O Godfrey is transforming its fourth floor rooftop into a haunteed manor, filled with dark secrets, eerie encounters and ghostly sights at every turn. Guests can also book an igloo reservation that comes with expedited entry to the party and a bottle of booze, but general admission tickets are also available for those who prefer to wander around and explore dance performances, DJ sets and spooky refreshments.

The River North nightclub—which, by the way, is housed inside a Gothic greystone building that's long been rumored to be haunted—is going all out for Halloween and hosting a House of TAO party on October 27, featuring reality TV star and personality James Kennedy as well as a DJ set from fan favorite Lil John. The venue will be decked out in over-the-top decor, including everything from dragons to photo-worthy thrones throughout.

Arr, matey! The world’s largest rooftop is transforming its expansive space into a haunted sunken pirate ship this Halloween. Put your best costume on and prepare to walk the plank—the evening will feature a four-hour open bar, passed bites, a costume contest and plenty of dancing.

Celebrate Halloween at this lavish party hosted by LondonHouse Chicago, where you'll find a premium bar and live DJs spread between the LH on 21 Lounge, Etoile Ballroom and rooftop space. Stick around for the costume contest that commences at midnight—the first place winner will receive an overnight stay at the hotel and two tickets to the upcoming New Year's Eve party. 

See the Blue Man Group with a touch of spooky (yet family-friendly) flair during these special Halloween weekend performances, where kids and their families are invited to show up early for pre-show face painting, Halloween surprises and goodie bags for little ones who wear costumes to the theater. After the performance wraps up, head back to the lobby for photo ops with the Blue Men themselves.

Head to the suburbs this Halloween season to check out the second annual Schaumburg Halloween Carnival, a seasonal fun fair that spans two weekends full of spooky rides, trick-or-treating, themed arts and crafts, and snack vendors, among other attractions. This year, Wintrust Field will also transform into The House of Creeps haunted house. Entrance to the carnival is free, but you can also opt to purchase ride wristbands for unlimited runs on Krazy Kabin, Matterhorn, Sizzler and other classic rides. Parking is $5 per vehicle.

The Chicago Athletic Association is throwing several spooktacular Halloween parties throughout October. Put on your best outfit for Masha’s Monster Mash, a karaoke costume party hosted by Masha Potato, on October 21. If you’re into spirits and witches, stop by on October 28 for Bazaar of the Occult to shop wares from 50 artists and makers, plus enjoy tarot readers and live performers. Finally, live up your ‘90s fantasies as the CAA transforms its White City Ballroom into a bold and elegant world for a Romeo + Juliet Halloween Ball on October 29.

Navy Pier is the site of a spooky immersive experience this October. Guests will delve into the mysteries of a once-renowned genetic plant laboratory, now transformed by grief into the Garden of Decay, by donning headsets and exploring rooms while guided by actors. The experience has been meticulously crafted with help from talented local artists, who have infused unique elements into each room. Afterwards, you can check out a world of interactive art, themed vendors selling treasures, tantalizing botanical cocktails, tarot card readings and many more activities in the Garden of reCreation.

The Peninsula Chicago hotel is offering a pop-themed sushi experience at its Lobby restaurant on Fridays and Saturdays through November 18. Cocktails named after nostalgic pop songs and a DJ spinning hits from the ‘80s and ‘90s will take guests down memory lane as they enjoy fresh maki rolls—like Crunch Smoke Lobster Maki and Spicy Scallop Maki—sashimi and nigiri, and prepared starters and entrees. There’s also an option for a special tasting menu if you prefer to leave everything up to the chef.

Returning to a two-acre plot of land just west of Goose Island, Jack's Pumpkin Pop-Up saves you a trip to the suburbs by bringing a huge corn maze, more than 10,000 pumpkins, axe throwing, carnival games, food trucks, twinkling orange light displays and more fall fun to the city. A general admission ticket nets you access to the pop-up, but you can also opt for add-ons that let you take home a pumpkin, grab a drink at one of bars or go axe throwing. 

Hosted at tropical bar Bamboo Club, this annual Halloween-themed extravaganza features a multi-level haunted house as well an upstairs bar serving spooky cocktails. Tickets for the haunted house (which is open to attendees ages 16 and older) are $20 or $30 for VIP, which includes a drink and express entry.

Embark on a 75-minute boat tour that explores Chicago's spooky past while winding through some of the city's most gorgeous architecture. The nighttime tour is hosted by a costumed tour guide who highlights infamous incidents and supernatural occurrences.

Test your knowledge of all things holy and haunted during Holy Ghost Bingo: God, Goblins & Games, an interactive comedy bingo show at the Greenhouse Theater where audience members get quizzed on Halloween and Catholic traditions alike. FYI: You'll actually be playing bingo for this one, so Halloween candy and other spooky prizes are yours for the taking. 

This annual festival assembles luminaries from the fields of politics, journalism and the arts for a multi-week series of programming across the city, with events ranging from lectures and discussions to screenings and musical performances. Not sure which events to hit? Some of this season's biggest speakers include Millie Bobby Brown, Keegan-Michael Key and Elle Key, Bob Odenkirk and Henry Winkler. You can see a full schedule of programming on the Chicago Humanities Festival website. 

Hamilton, writer-composer-lyricist Lin-Manuel Miranda’s biography of Alexander Hamilton as refracted through a hip-hop, pop and R&B lens, is a sprawling, stunning, singular achievement. It returns to Chicago for another run this September through December. Check the official website for the full schedule.

Based on the family-favorite board game, this new immersive and interactive experience puts guests into the roles of beloved CLUE characters as they try to solve a murder mystery. The game starts at Block 37, where detectives are greeted by the Butler before being sent on their way to gather clues from popular Chicago sites and shops. You’ll be tasked with finding long-lost antiques and figuring out who did it, where and with what.

Rooftop Cinema Club, the open-air theater perched atop The Emily Hotel, is back for a second season. Guests can catch showings of hand-picked classics, cult films and recent releases while also enjoying sweeping views of the skyline and craft beverages. It’s the perfect summer cinema experience.

Originally established in the late 1800s, the Maxwell Street Market brought vendors, musicians and cooks to an open-air flea market where shoppers could find just about anything they wanted. The market introduced the Maxwell Street Polish sausage, provided a venue for rising Chicago blues musicians and was immortalized in a scene in The Blues Brothers. These days, the market sets up on nearby Desplaines Street (between Roosevelt and Howard) every Sunday, where visitors will find vendors hawking their wares, an abundance of delicious Mexican food and occasional performances by local bands and dance troupes. Don't let the cold or wet weather scare you away—the Maxwell Street Market takes place outdoors year-round.

Head to 360 Chicago on Saturdays for yoga with a killer view. Instructor Britta Eumann will lead an hour-long class on the 94th floor of 875 N Michigan Avenue (formerly the John Hancock Center) that’s suitable for all ages and skill levels—you just need to bring your own mat and arrived properly dressed. Registration is $50 and includes a cocktail or coffee, plus admission to the observation deck so you can stick around and snap some photos after you're done striking poses on the mat.

Displaying a 25-story-tall video installation on the side of the Merchandise Mart, ART on THE MART is the largest permanent digital art projection in the world, with programming that changes seasonally. ART on THE MART's array of 34 digital projectors show the creations after dusk every evening. It’s best viewed from the section of the Chicago Riverwalk between Wells Street and Franklin Street.

Bye Bye Liver combines two robust Chicago traditions: comedy and heavy drinking. The show opened a decade ago for a three-week run, then kept getting extended. A cast of four to six performers portray characters at the fictional "Franks Bar," telling stories that explore the city's robust drinking culture. Each show incorporates interactive audience drinking games, allowing you to sip a cocktail or beer while taking cues from the cast. And if you're up for a nightcap after the performance, you can stick around for the official after party and mingle with the cast.

Settle in for an evening of burlesque performers, belly dancers, drag artists and variety entertainers during this weekly show at Newport Theater. The hour-long show features speciality cocktails and intimate seating arrangements, making this feel like a clandestine speakeasy experience. Bring some singles so that you can tip performers throughout the night!

For more than 30-years, the Neo-Futurists have been delighting late-night crowds with performances that pack 30 miniature plays into a 60-minute show. Returning to in-person programming (attendees must be vaccinated and masked) after more than a year spent in the virtual realm, the company's signature show is more unpredictable than ever, with a handful of compact new plays premiering every week. Within the span of 10 minutes, you may be treated to a poignant monologue about everyday life or an irreverent diatribe delivered by a pantsless member of the cast—all inspired by the experiences of the performers on stage. Always changing and evolving, it's the rare show that truly offers something different everytime you show up to see it.

This weekly “live magazine” is a cavalcade of culture, politics and wit featuring journalists, actors, comedians and musicians offering idiosyncratic reports on the news of the day. Head to Uptown’s iconic Green Mill for drinks, hot takes and laughs; the longstanding Saturday afternoon edition tends to run about two and a half hours.