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The Graystone Tavern

The Graystone Tavern in Wrigleyville will host a Vikings-themed Halloween party on Sunday, October 31 at 6 p.m. A Minnesota Vikings-affiliated bar, Graystone will broadcast the game vs. the Dallas Cowboys at 7:20 p.m., and guests who dress to impress in their best viking costume will receive a FREE Skol Bomb (Three Olives Grape with Red Bull Blue edition).

There will be a viking costume contest with the winner receiving a $200 Graystone gift card as well as game day raffles with proceeds benefiting the October charity of the month, The Lynn Sage Foundation. Drink specials will include $5 Skol Bombs, $5 Surly Furious Drafts, $20 Coors Light & Miller Lite Buckets, $25 Truly Hard Seltzer Buckets and $12 Juicy Lucy. 

The Rambler Kitchen + Tap

The Rambler Kitchen + Tap in North Center will host a full day of Halloween festivities beginning with a Big 10 Football Spooktacular for the Iowa vs Wisconsin game at 11 a.m. on Saturday, October 30. Specials will include $5 stadium food specials, $5 shots of Paddy’s and Skrewball Whisky and $20 Domestic Buckets. The game will be shown with sound on 24 TVs throughout the bar. Reservations can be had by emailing

From 8 p.m. to 12 a.m., The Rambler will host a Halloween “Monster Bash: Til Death Do Us Party” featuring a $40 drink package including all drafts, import, domestic beer and call liquor. There will be a costume contest with the best costume winning $100. The best group costume (2 to 6 people) will receive $200 or a full refund on their party package fee. Packages can be purchased at 

Rewired Pizza Cafe & Bar

Rewired Pizza Cafe & Bar in Edgewater is getting in on the Halloween fun this year by paying homage to classic restaurant chains and “dressing up” as owner Daniel Barat’s favorite pizza chain. From Thursday, October 21 through Sunday, October 31, Rewired will become “Dominoes” complete with fun decor in the signature red and blue color palette along with a themed menu available from 11 a.m. to close daily. 

The pop-up will feature specialty pizzas available in small ($16), medium ($20) and large ($24) like Hawaii Honolulu (bacon, pineapple, ham, red pepper and red sauce), Phil’s Cheesesteak (white sauce, steak, peppers and onion), S’pacific Veg (onion, roasted red pepper, baby spinach mushroom, tomato, black olives, feta and mozzarella), and Tennessee BBQ Chicky (roasted chicken, fresh onion, BBQ base, cheddar and mozzarella).

“Dominoes” will also serve a selection of Baked Rigatoni Pastas for $11.60 each including Alfredo Chicken, Carbonara Chicken and Primavera. Sandwiches for $9.49 each will include Spicy & Sweet Habanero Chicken (grilled chicken thighs, jalapenos, pineapple, sweet marinara and melted cheese), Phil’s Cheesy Steak (tender steak, cheese sauce, peppers and onions) and more.

Created by Beverage Director, Robert Christopher Schultz, guests can order a Orange Creamsicle Slushie cocktail along with other cocktails inspired by old school chains.

Uvae Kitchen & Wine Bar

On Halloween, Uvae Kitchen & Wine Bar in Andersonville will partner with The Dinner Detective team to host a five-course Murder Mystery Wine Dinner on Sunday, October 31 at 6 p.m. with seating starting 5:30 p.m. and 5:45 p.m. For $138 per person, guests will have dinner and show as they dine on a five course menu with wine pairings.

Highlights include Arugula & Fennel Salad with warm brie croutons, honey crisp apples, candied walnuts and fennel frond vinaigrette, Pumpkin Soup with crème fraiche, spiced pepitas and cilantro, and a choice of entree like Pan Seared Scallops, Roasted Duck Breast, Braised Short Rib, or Roasted Maitake Mushrooms served with truffle risotto and black currant reduction. A Salted Caramel Apple Tart will be served for dessert. 

Costumes are encouraged, and space is limited. For reservations, visit


Guests can visit WhirlyBall in Chicago, Naperville and Vernon Hills and choose from several Halloween party options including a kid-friendly costume party and a separate adults-only costume party. Complete details are available below and tickets can be purchased at the door or ahead of time by visiting

Family Fun Halloween Costume Party

  • Select from two dates: Sunday, October 24 or Saturday, October 30 from 10 a.m. to 1 p.m.
  • $30 adults; $20 kids

Activities included in the ticket price are WhirlyBall, LaserTag, Bowling and other pop-up games. From 10 a.m. to 12 p.m. guests can order a food buffet featuring assorted pizza, sliders, chicken fingers, and mac and cheese. For dessert, brownies and cookies will be available from 12 p.m. to 1 p.m. Soda and fountain drinks are included, while alcoholic beverages are cash bar.

Devil’s Night Adults-Only Costume Party 

  • Saturday, October 30 from 8:30 p.m. to 11 p.m.
  • $75 package

On Devil’s night, Saturday, October 30, WhirlyBall in Chicago, Naperville and Vernon Hills will host an adults-only costume party featuring a $75 per person package which includes food, activities, beer and wine from 8:30 p.m. to 10:30 p.m.

Activities will include WhirlyBall, LaserTag, Bowling and other pop-up games. Dinner will be served buffet-style from 8:30 p.m. to 10:30 p.m. and will include The Pivot Chopped Salad, assorted Pizza (cheese, sicilian, caprese, Italian sausage & peppers), Classic and Buffalo Chicken Sliders, and Pretzel Bites. A dessert station will be available from 9:30 p.m. to 10:30 p.m. with fresh-baked brownies and cookies. 

Photo courtesy of Uvae Kitchen & Wine Bar

Lottie's Pub

Lotties Pub (1925 W. Cortland St) is celebrating spooky season with Lottie's Camp of Horrors, a Halloween pop-up experience featuring seven decorated "Tents of Terror", starting Monday, October 11th. 

Guests can also partake in "Tent Flix & Thrill" movie nights, where groups can watch their favorite Halloween films in the comfort of a private heated tent. Movie nights will run from every Tuesday & Wednesday, from October 12th to October 27th, at 5:30 to 8 PM. Features include Friday the 13th, Scream, & Halloween, as well as Hotel Transylvania, Hocus Pocus & Monsters Inc for those looking for a family friendly film.

Lottie's full food and drink menu will be available. Tents can be reserved by emailing

Camp Of Horrors
Flyer courtesy of Lottie's Pub


Happy haunting. Offshore, located on the third floor of Navy Pier, 1000 East Grand Ave, is hosting two Halloween themed events throughout October to get Chicagoans spooked. The two inclusive events will include a themed Paint and Sip party with local studio Pinot’s Palette on Wednesday, October 20, along with a Halloween Costume Party for those looking to slay on Saturday, October 30. Tickets to both events are limited, and available now for purchase.  

First-time painters and experienced artists are invited to join Offshore as they partner with Pinot’s Palette for a spooky painting party on Wednesday, October 20 beginning at 6:30 p.m. Patrons will be led through a Halloween-inspired skyline painting led by a local artist from Pinot’s Palette. Tickets for the paint and sip event, each $68, include two glasses of house red, white, or rose wine, along with paint supplies, a blank canvas and aprons. Additional drinks will also be available for purchase during the event. The evening will take place indoors on the rooftop in Offshore’s airy glass atrium, which includes collapsible floor to ceiling windows that give a great indoor/outdoor atmosphere. Tickets are limited and can be purchased by clicking here 

Best buds and boos 21+ are also invited to Offshore’s Halloween Party on Saturday, October 30 beginning at 8 p.m. Tickets are $95 each, and include access to a premium four-hour bar, along with passed bites. Throughout the night, there will also be a costume contest with over $2,000 of prizes and a complimentary hotel stay at Sable at Navy Pier for the first-place winner who killed the competition, along with plenty music, dancing and more. Tickets can be purchased by clicking here. 

Please note, tickets to both events are non-refundable, and masks are required upon entry, exit, and movement around the space. 

Screen Shot 2021 10 12 At 12 31 44 Pm
Photo courtesy of Offshore

The Gwen Hotel

Spooky szn is here and The Gwen Hotel in Chicago is celebrating with a Tarot Cocktail Menu available all month long along with programming like Halloween Classics on the Terrace, where guests can partake in some of cinema’s scariest films and have their Tarot cards read.

Austin Ryan, Director of Food & Beverage at The Gwen was inspired by an imagined Tarot card reading of Gwen Lux, the sculptor the hotel was named after when creating the Tarot Cocktail Menu.

Halloween Classics on the Terrace

·         Wednesday 10/13/2021 – 6:30p

o   Night of The Living Dead (1968)

·         Wednesday 10/27/2021 – 630p

o   House on Haunted Hill (1959)

Tarot Cocktails The Gwen 2
Photo courtesy of The Gwen Hotel

Pilot Project Brewing

  • Pilot Project will host Pilates & Pumpkin Painting on Saturday, 10.23 at 10am.

  • Alex Green, founder of Sweat to Reset, will lead a 45-minute Pilates HIIT Hybrid class. This movement session will immediately be followed by pumpkin painting and drinks. The ticket price ($28)  includes a 45-minute movement session, pumpkin, paint supplies and a beverage of choice!

  • Link to purchase tickets here.

You’re A Cookie!

  • Monster Mash Pop Up at the soon-to-open storefront (3053 N. California Avenue) on Friday, 10.29 (4pm-9pm), Saturday, 10.30 (2pm-9pm) Sunday, 10.31 (2pm-9pm). Stop by and get a Monster cookie, Triple Chocolate Chip or Vegan Chocolate Chip cookie. The pop up will have a spooky ambiance and include music, decorations and hot apple cider. Guests who stop by in costume will get 10% off.

    • The speciality item for sale will be the Monster Cookie (Chocolate and brown sugar swirled cookie packed with candy corn, marshmallows, pretzels and caramel chunk). The vegan version will also be available, along with ice cream sandwiches. Toppings include green fluff, graveyard dirt (chocolate cookie crumbs, candy eyeballs, gummy worms).

    • Monster Cookie Stacks $15

    • Monster Cookie Cake $30 (Our Monster cookie with spooktacular frosting, eyeballs + worms... Perfect for your halloween party). Pre order only.

    • Nationwide Shipping: Pre order online from 10.15-10.24. 

    • Local Pick Up: Pre order online from 10.15-10.27 -- Pickups will be at the pop up only.

  • Seasonal Cookies: Fall flavors available online now and in store (when it opens) through 11.15

    • Apple Cider Oatmeal (Fresh apples, Mexican cinnamon, vanilla, brown sugar)

    • Pumpkin Spiced Snickerdoodle  (Pumpkin pie, pumpkin spice sugar)

    • $3/ea (in store), $15/ stack (half dozen)  


  • Bringing back its Pumpkin Whoopie Pies for the month of October. 

  • On Halloween weekend, every costumed kid under the age of 12 will receive a special treat at the bakery.

Pumpkin Whoopie Pies
Photo courtesy of Hewn


Thrills turn to chills now through October 31 as 360 CHICAGO Observation Deck at the former Hancock Building introduces TILT Terror Nights with special tickets that include admission from 6 PM until close with views to die for, a more terrifying ride on TILT, and a creepy cocktail (or mocktail) from BAR 94.

Creepy Halloween cocktails at BAR 94 include:

  • Buffy’s White Russian

House vodka, Kahlua, half & half, infused with pumpkin spice flavor. Garnished with a stake through a marshmallow heart with cherry “blood.”

  • Cranberry Zombie

Three types of rum – white, dark, and spiced – with pineapple juice, orange juice, grenadine, dried cranberry “brains,” sugar eyeballs, and passion fruit “blood

Pricing is (Adult/Youth):

  • Valid 6 p.m. and later every night through Oct. 31
  • All Access includes Admission, TILT and BAR 94 Cocktail: $49/$39
  • TILT & View Only: $40/$30


Screen Shot 2021 10 13 At 10 56 28 Am
Photo courtesy of 360 CHICAGO

Azul Mariscos

Azul Mariscos is offering their Torre de Margaritas (Patron Margarita Tower) which will be available all Halloween weekend for $75

Takito Street

In celebration of Dia de los Muertos (Day of the Dead,) Mexican Hot Chocolate (served with a Giant Marshmallow) will be available all Halloween Weekend. 

Fame Supper Club

Fame Supper Club's, Lady In The Ashes, is a spooky cocktail inspired by a historic murder. Made with Ron Matusalem Dark Rum, Muddled Cantaloupe, Coconut Cream, Simple Syrup, Fresh Lime Juice & Activated Charcoal.


The Halo-Halloween dessert is available the entire month of October. A spooky take on the Filipino restaurant’s signature Halo Halo Dessert, the Halo-Halloween is a cold, layered dessert of shaved ice and condensed milk, ube jam, Kaong, Nata de Cocoa, rice crispies & housemade ice cream.

Halo Halloween
Photo courtesy of Cebu
Halloween Cocktail 2021 Ambassador Chicago
Photo courtesy of Ambassador Chicago

Boxcar Betty's 

This Halloween weekend, Boxcar Betty’s will award one adult with BOGO For Life and one child (age 12 or under) with Free Nuggets until age 18 with their spooktacular “BooGo” promotion. On Friday, Oct. 29 and Saturday, Oct. 30, any guest who visits the Bucktown restaurant and purchases one of Boxcar’s Betty’s fried chicken sandwiches will automatically receive an additional free sandwich of their choice. Guests are able to mix and match their “BooGo” sandwiches by purchasing either the Boxcar, Chicken “Not So Waffle”, Buffalo or The Betty and selecting any of the four sandwiches for their additional free item.

Guests who wear a Halloween costume in the restaurant when placing their order will automatically be entered into the raffle to win one of the two prizes. Adults in costume will have a chance to win ‘BOGO For Life’, allowing the guest to have access to the BOGO promotion 365 days a year for the rest of their life. Children, in costume and age 12 or under, whose parents purchase a sandwich, will be entered into a separate raffle to win ‘Free Nuggets until age 18.’ One adult winner and one child winner will be selected at random during the course of the promotion.  

*Note: the promotion is not available at the Ogilvie location, only Bucktown. 

Screen Shot 2021 10 15 At 4 05 57 Pm
Photo courtesy of Boxcar Betty's

Cocoa + Co.

Cocoa + Co., a coffee and chocolate café nestled in Chicago’s historic Old Town neighborhood, will be offering a number of seasonal treats in anticipation of Halloween this month.

Executive Pastry Chef and Partner, Meg Galus, will be preparing a limited edition Halloween Pastry Box, which will include Black & White Marble-Frosted Sugar Cookies, Charcoal Black Cookies & Cream Croissant, Black Sesame Pumpkin Doughnut and a Ghostly Rum and Vanilla Bean Canele. Boxes can be pre-ordered beginning Monday, October 18th on Cocoa + Co.’s website (, and will be available for pick-up at the cafe over Halloween weekend.

Additionally, for service in the cafe, they’ll be featuring their signature Pumpkin Drinking Chocolate (made with real pumpkin puree), Pumpkin Whoopie Pies, colorful Halloween Chocolate Bark, intricately decorated Day of the Dead Cookies and a Spider Web Cake, as well as a selection of Ghoulish Bonbons, Splatter Skulls and Eyeballs (among other themed confections).

Cocoa Co Skull Cookies
Photo courtesy of Cocoa + Co.


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