Keep those eyes peeled for Freddy Kreuger at this Wrigleyville bar’s Nightmare on Clark Street pop-up, which runs through Sunday, October 31. Staff are betting that thirsty reveler’s mouths will say yes, yes to Halloween drinks like the Monster Mash (Malibu, Midori, pineapple, Sprite) garnished with eyeball and worm candies and Jell-O shot syringes, plus sugary bites such as s’mores brownies. Reservations, which are free and available online, are capped at an hour and a half for parties of no more than six.

Craft brewery and taproom Hopewell on Saturday, October 30 will transform into a Bob’s Burgers pop-up starring cheeseburger taquitos (vegan options available) from Kite String Catina. The taproom is also a stop on a Beers for Fears trolley crawl that will also include Middlebrow, Solemn Oath, Marz Community Brewing, and Orkenoy. The trolley will stop at each brewery between 3 p.m. and 5 p.m., and patrons to visit all five breweries may earn a prize.

The team at Logan Square hit Longman & Eagle will host a pumpkin carving event from noon to 5 p.m. on Sunday, October 24 with seasonal treats like apple doughnuts and hot cider (they also promise lots of Jim Beam). Some complimentary pumpkins and carving kits will be available, but attendees can also BYOP to make sure they get in on the messy fun. Proceeds from food and drink will go to abortion-access nonprofit Texas Equal Access Fund.

Psychedelic rooftop spot Utopian Tailgate in Old Town is also applying a funhouse twist for Halloween, becoming “Dystopian Tailgate” on Friday, October 29 and Saturday, October 30 for a spooky circus party with food, drinks, and costume contests. Revelers can also have their tarot cards read and catch performances from acrobats, jugglers, and fire-twirlers. Ticket packages ($250-$500) and more details are available via Eventbrite.

This lauded cocktail bar will embrace the creepiest season with the Violet Hour Creature Feature, a two-day celebration of American horror and cinematic scares of the ‘70s and ‘80s — think Carrie, the Thing, and Sleepaway Camp. Costumes are highly encouraged (preferably one that allows for dancing), and patrons can expect an open bar with holiday-themed drinks, snacks, and possibly a slushy “as black as night.” Tickets ($125) and more details are available via Tock.

Cozy and casual, Heritage Restaurant & Caviar Bar will bring back its seafood chain-inspired pop-up Dread Lobster its second year, getting into the silly mood with costumed staff and a special menu featuring mini cheddar biscuits, High Life-battered cod with tobiko tartar sauce, and “tombstone-sized” mozzarella sticks with beet cocktail sauce. The special menu will be available from 4 p.m. to 9 p.m. October 25 - 31.

In a remarkably quick turnaround, this downtown cocktail spot aims to harness the power of South Korean TV sensation Squid Game starting at 8 p.m. on Friday, October 29. Free reservations are available via Eventbrite. True to its source material, the pop-up hasn’t shared many details save for a few key points: “All inhibitions will be eliminated. Anonymity is of the utmost importance. Mask wearing VIPs will receive welcome punch. I’ll repeat the instructions. All inhibitions will be eliminated. Anonymity is of the utmost importance. Mask wearing VIPs will receive welcome punch. No Cover. Green light.”

For a Halloween treat that is both ghoulish and gorgeous, pop into top-notch bakery Aya Pastry to and check out the special Halloween-themed bonbons from Elle Lei of SUGOi Sweets. Lei is hand-painting the bonbons to resemble jack o’lanterns, bloody eyeballs, spiders, and even Monsters Inc. cyclops Mike Wazowski. Inside, customers will find flavors like candy corn, green apple Pop Rocks, and pumpkin pie. Preorders boxes of six or 12 online for pickup at the bakery starting Saturday, October 23.

Massive West Loop patio spot Recess likes to go big, and this Halloween celebration is a case in point: at 8 p.m. on Friday, October 29, it will become an apocalyptic, zombie-ridden Las Vegas a la Netflix hit Army of the Dead. Partiers can count on holiday food and drink menus, games, and a costume contest with a $500 prize. Tickets ($10) and more details are available via Eventbrite.

Over-the-top River North venue Untitled will mark Halloween with “the Howling 20s,” a party designed to celebrate the “decadence, delight, and (sometimes) danger” of the era. Reps promise three rooms packed with contortionists, pole, and burlesque dancers, plus dance music from DJ Zebo. Costumes are strongly encouraged. Tickets ($10-15) and more details are available via Eventbrite.

Ace Hotel will this year throw a three-floor Halloween bash called “As Above, So Below” centered around raucous attractions like “illusions,” burlesque performances, tarot readings, a costume contest, and more. Don’t show up in a humdrum outfit — costumes are required for entry. Tickets and table reservations are available via Resy.

Adult Halloween and kid Halloween are not the same thing, so those in search of an occasion that’s appropriate for families may find success with a kids costume party at 5 p.m. on Friday, October 29 at Top Chef champion Stephanie Izard’s Little Goat Diner. Activities will include pumpkin painting, finger foods, dancing, and lots of treats from Izard’s kooky bakery Sugargoat. Tickets ($25) and more details are available via Tock.

This festive spot on Randolph Restaurant Row is spreading around the Halloween fun with daytime and evening celebrations. Details are still trickling out, but there’s a ‘90s MTV Music Video Awards-themed event slated for Friday, October 29 and Saturday, October 30. Those who would rather party early can try the Halloween Bottomless Brunch from noon to 3 p.m. on Sunday, October 31 with food, cocktails, and holiday activities like a costume contest and pumpkin decorating. Reservations and more details are available via Tock.

Maria’s annual Halloween dance party will return as “Gravedigger Disco” from 7 p.m. to midnight on Saturday, October 30 with music from DJ BLUNTGOD and Decept. Patrons will be required to show proof of vaccination.