A dog and its owner pose in costumes at Cody's Public House
Photograph: Courtesy of Cody's Public House
Photograph: Courtesy of Cody's Public House

The best things to do in Chicago this weekend

Find the best things to do in Chicago this weekend with our guide to concerts, exhibitions, festivals and more.

Shannon Shreibak
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We’re probably not alone in saying that the weekend is always on our minds here at Time Out Chicago HQ. Like you (probably), we spend the workweek daydreaming about the next restaurant to obsess over and obsessively updating our concert calendars. Whether you’re museum-hopping, plotting a day trip to escape the city, or ready to ghost your original plans for something spontaneous, you’ll find plenty of ways to make the most of your weekend in Chicago.

Last updated October 22, 2025: Praise be—Chicago is finally settling into fall weather, and the city has the perfect events to pair with these crisp temps and changing leaves. Animal lovers can enjoy not one, but two animal-centric Halloween celebrations: the Streeterville Doggy & Kitty Halloween Party and a Howl-O-Ween Costume Contest at dog-loving bar Cody’s Public House. For those seeking boozy Halloween revelry, enjoy pop-ups like Nightmare on Clark Street, Black Lagoon and Curse of the Nile. If you’re saving all your festive energy for Halloween weekend proper, catch a flick at the Chicago International Film Festival or support local makers at KOVAL Distillery’s Ravenswood Makers Market.

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The best things to do in Chicago this weekend

  • Things to do
  • Quirky events
  • Streeterville

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—chosen by Alderman Brian Hopkins and Streeterville resident Maureen Schulman—will receive prizes. Donations support the the dogs, cats, kittens and puppies residing at PAWS Chicago.

  • Kids
  • Lincoln Park

Get your fall feels on at this free festival that begins at the tail end of September. You can snag a photo with a giant pumpkin, watch master carvers at work, enjoy live music and see all kinds of animals. The festival also includes several ticketed experiences such as carousel rides, a bounce house, harvest maze, a slide and more. 

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  • Shopping
  • Markets and fairs
  • Lake View

Head to KOVAL Distillery to shop a variety of goods from 25 local artisan makers. You’ll be able to peruse items like jewelry, knit goods, home decor, prints, paintings, candles and more. KOVAL will also be stocked with plenty of candy for those wanting to do a little little trick-or-treating, whether that be adults or kiddos.

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  • Things to do
  • Lake View

Chicago’s pups are taking center stage this spooky season at Cody’s Public House. Famous for its dog-friendly vibe both indoors and out, Cody’s will transform into a tail-wagging Halloween celebration with its Howl-O-Ween Costume Contest. At 4pm, furry friends and their humans can strut their stuff for a chance to win cash prizes. Guests can also enjoy raffles benefiting ALIVE Rescue, free pup cups and a special “pup-tail” menu.

  • Things to do
  • Quirky events
  • Washington Park

In addition to the regular Arts in the Dark parade on State Street, the arts organization LUMA8 is hosting a "reverse" parade—in which attendees pass through a stretch of costumed performance groups lining Russell Drive in Washington Park. Bonus: At the end of the route, attendees will get a complimentary candy bag and other goodies. Come wearing your best Halloween costume!

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  • Cocktail bars
  • Lincoln Park

Spooky season will get a bit boozier this year thanks to this horror-themed cocktail pop-up at the Albion Manor, where Halloween lovers can sip expertly mixed cocktails amid metal music and goth decor. Drinks are imbued with playful touches and include choices like Corpse Flower (tequila blanco, ube, Giffard Banane, lime, sherry) and Griselda’s Revenge (gin, vermouth, tarragon, thai spice). 

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  • Things to do
  • Performances
  • Loop

The masterminds behind the irreverent long-running comedy show Drunk Shakespeare are unleashing their latest monster mash-up, “Drunk Dracula,” on the city during the month of October. The premise is simple, but no less hilarious: Dracula gets drunk, unsuspecting citizens fight for survival and Bram Stoker’s vampire classic gets a boozy makeover that’s equal parts unhinged and fun.

  • Things to do
  • Quirky events
  • Wrigleyville

Hosted at Stolen Saddle—one of Chicago's newest and largest country bars—this annual Halloween-themed extravaganza features photo ops galore as well an upstairs bar serving spooky cocktails like Freddy’s Tequila and Monster Mash. With the Cubs clinching a playoff spot this year, there’s no haunted house this go-around—but that doesn't mean Nightmare on Clark Street won't be serving up scares this Halloween season.

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  • Things to do
  • Festivals

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. 

  • Shopping
  • Markets and fairs
  • Lake View

More than 140 artisan vendors show off handmade home decor, art, clothing, jewelry and more at the fall edition of Market for Makers, a two-day event that brings together crafty people from across the country. Every guest receives a tote bag, access to fun photo ops and a DIY Station where you can create a unique keepsake.

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  • Things to do
  • Quirky events
  • Lincoln Park

Every October, Rough House Puppet Arts creates a brand new immersive production to celebrate spooky season. House of the Exquisite Corpose, Chicago's one and only haunted house staffed by puppets, returns for its fifth year for a new immersive experience. For House of the Exquisite Corpse V: Blood & Puppets, six teams of Chicago artists orchestrate six unique and terrifying puppet-driven vignettes—all inspired by the theme “blood.” 

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  • Art
  • Film and video
  • Recommended

Displaying a 25-story-tall video installation on the side of THE 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. Running Thursdays through Saturdays beginning at 7:30pm, it’s best viewed from the section of the Chicago Riverwalk between Wells Street and Franklin Street.

  • Streeterville

A terrifying story set in the world of the Paranormal Activity film franchise, Felix Barrett (Sleep No More) and Chicago playwright Levi Holloway's latest endeavor promises chills and thrills. Here's what you need to know: James and Lou flee from Chicago to London in hopes of escaping the past, but they soon discover that it's not the city that was haunted—it's them. 

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  • Things to do
  • Exhibitions
  • Lincoln Park

Experimental Sound Studio's longtime partnership with the Chicago Park District and Lincoln Park Conservatory continues with “Semblance of Fern,” a new sound installation by composer Sarah Belle Reid. The immersive installation explores the formal connections between mathematical models and nature in the contemplative confines of the conservatory's Fern Room. After getting your fill of tropical palms and vibrant flowers, mosey over to the Alfred Caldwell Lily Pool, which is free to visit and recently reopened to the public.

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  • Comedy
  • Uptown
  • Recommended

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.

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  • Movies
  • Streeterville
  • Recommended

Some of the latest and greatest movies to hit the festival circuit arrive in the Midwest during the Chicago International Film Festival, which typically presents a lineup of around 100 dramas, documentaries, comedies and foreign films, plus 60 short film programs. In addition to CIFF's home base at AMC Newcity 14, the fest offers viewing opportunities across the city, with screenings at the Music Box Theatre, the Gene Siskel Film Center and more. 

  • Attractions
  • Parks and gardens
  • Suburbs

Get in the holiday spirit at this annual ghoulish makeover of the Chicago Botanic Garden. The event brings together more than 1,000 real pumpkins—some weighing up to 150 pounds—which are LED-lit creations and staged along the garden's pathway where other entertaining characters and activations await visitors. Seasonal snacks and drinks are available for purchase, in case all that wandering makes you hungry. 

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  • Things to do
  • Festivals
  • Suburbs

Round up your family for a wild, multi-weekend Halloween festival perfect for all ages to enjoy. Decorate a pumpkin, take a spin on the decked-out carousel or pose for photos amongst giant inflatables and wooden cut-outs of Halloween characters. The not-too-spooky event also treats some of the zoo's animals—including capybaras, polar bears and gorilla—to pumpkins that they can play with, nibble on and smash. 

  • Things to do
  • River North

This Halloween, the I|O Godfrey rooftop transforms into an ancient tomb unsealed, where ancient curses awaken and the dead stir beneath the stars. The event will include a winding labyrinth, immersive decor, themed cocktails, private igloos, live DJs and more. Enter if you dare...

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  • Things to do
  • Walks and tours
  • Streeterville

Step aboard City Cruises’ Seadog for a fun-filled journey through Chicago's history of ghosts, spirits, scandals and sins. As guests cruise along the Chicago River for 45 spooky minutes, expert—and costumed—docents weave stories of Chicago's darker side while cruising through the city's most iconic architecture. The cruise is BYOB, so be sure to bring a bevvy of your choice. 

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