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As we prepare for uncharted territory this winter, some concepts are taking Halloween as an opportunity to celebrate autumn with creative offerings. 


Halloween Cocktail (available in person only)

  • Burning Budd ($16, bourbon, pear, smoked tea, pistachio, basil)


  • Game Day Meals ($39, feeds 2) *Available for pick-up through their Tock every Saturday/Sunday between 11am-5pm 
    • Inclues: Italian sausage, red sauce, peppers & onions, pre-sliced buns, duck fat fries, side of homemade giardiniera, chocolate chip cookies
  • NY-Style Pizza *Just launched, Available everyday, served individually. (Slice $6, Whole Pie $28) 
    • Meatball and Giardiniera Mozzarella, Dried Oregano
    • Pepperoni, Mozzarella, White Truffle Oil, Fresh Oregano
    • Margherita, Bufala Mozzarella, Basil, Olive Oil, Maldon Salt
  • Lasagna *Launching soon  
  • Halloween Whimsical Candies and Treats *Available in person only ($3 per bag)
    • Ever-changing treats including: caramel apples, wrapped caramels, mini-ice cream sandwiches, Trixie Treats, raspberry & rose jellies, chipotle orange cake truffles


Halloween-inspired specials will be offered in person or ordered through Toast here

  • A Stake Through the Heart (beef heart skewers, lingonberry mustard, doenjang glaze). 
  • Honeycrisp Apple Salad (honeynut squash, pepper jelly, lime yogurt, pumpkin seed dukkah)
  • Turkey Leg Tostada (refried black beans, salsa negra, pickled red onion, queso fresco). 
  • Funnel Web Spider (funnel cake, black lime meringue, raspberry-rose coulis).   


Pumpkin Patch, Fall Menu, Fall Market Items. For bookings, reservations, online ordering, and more, visit their Tock page. 

  • Pumpkin Patch + Family Portraits
    • Pumpkins available for $10 each
    • Pumpkin Patch and Halloween family portrait sessions with various Chicago photographers on the following dates: 10/17, 10/24, 10/31. 
  • Fall Sandwiches *Available for lunch every Wednesday - Sunday starting at 11am
    • Sweet Potato Panini (fresh chèvre/calabrian chili/salsa verde). 
    • Italian Lamb (braised lamb/giardiniera/provolone) 
  • Fall Market Items *Market is open Wednesday - Sunday starting at 10 AM
    • This month they have fall produce favorites like apples, pears, squash, sweet potatoes, kale, and more. 
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The Turkey Leg Tostada at Gadabout (Courtesy of Gadabout)

Recess Chicago 

  • Recess Chicago is celebrating this Halloween, Saturday, Oct. 31, with “The Spirits of Halloween” – a reverse adult trick-or-treating experience with spirits and liquor sampling. Groups can purchase tickets for $35 per guest and receive spirit tastings and complimentary light appetizers, which will be delivered safely to each table (max. 6 guests). There are three two-hour time slots available for booking on the 31st: 5-7pm, 7:45-9:45pm and 10:30-12:30pm. The event will take place in the City Hall event space next door to Recess. 
  • A pop-up Halloween marketplace and Halloween cake competition is headed to Chicago’s Recess. Starting Monday Oct. 26 through Sunday Nov. 1, the daily programming includes spooky prepackaged candy bags and ghostly activities for the little ghouls from 2:30-4pm weekdays and 10-11:30am weekends, plus a fortuneteller, sinfully themed beverages and potions and merchants surviving up tricks and treats for days. Tickets for 1.5 hours time blocks start at $20 for adults, which includes one Halloween Cocktail plus 10% off food at Recess or free appetizer, $12 for kids under 13 and free for kids under three — available on Eventbrite. 
  • Give man’s best friend a reason to strut their stuff this Halloween at Recess’s first Dog Costume Contest. On Tuesday, Oct. 27 starting 5:30 p.m., bring your pooch in their most fashionable costume and strut their stuff on the way into the restaurant. A $15 donation is required to be entered into the contest and raffle tickets can be purchased for $5, of which proceeds will benefit Mission Compassion Paw. Entries close at 6:30 p.m. and the winner will be announced at 7 p.m. Raffle prices include Paw Naturals gift cards, an Airbnb weekend staycation in Wicker Park, booze basket, entry to Room 237, and more. 
  • Chicago’s 2nd annual Titan Walls Mural Festival is popping up at Recess’ patio this month, Oct. 16 & 17. Attendees can observe live painting on the patio’s shipping containers by two local artists, Caesar Perez and FEDZ. Muros is the agency behind the festival, as well as massive murals across the city. Recess and Muros partnered together earlier this summer to commission the “Dipso the Monkey” by Mosher and multiple other works of art on the shipping containers. 
  • Recess just installed more flat-screen TVs throughout the bar  — with no table time limits on Sundays. Guests will have space to cheer on their team while being offered drink specials just for game days on Sundays, including: $8 Absolut bloody marys, $8 Maestro Dobel cocktails, $10 Bacardi hurricanes, and $25 Truly buckets. Bonus for the Bears fans: they are raffling off a Bears jerseys during every Bears game this season. 

Morgan MFG. 

  • Morgan MFG. has been transformed to welcome you to “Room 237” — a pop-up experience and lounge inspired by The Shining, where you check-in as a guest to the Overlook Hotel. Guests can explore the multi-room pop-up experience, including a giant hedge maze and various interactive photo-ops such as the Redrum Door, Typewriter, Dogman, Bathtub, Staircase Battle, Hedge Maze, Trike Ride, Elevator, and of course: the Twins. Themed cocktails by mixologist Alex Brick include “Redrum,” “Come Play With Us,” “Hedge Maze,” “Apollo 11,” “Snowed In,” and “Timbuktu to Portland Maine.” Starting Thursday Oct. 15, Room 237 will be open Wednesdays to Sundays from 6 p.m. to 11 p.m. Tickets start at $35 per person and include one cocktail and can be purchased on OpenTable.

Artifact Events

  • Visit Artifact Events’ open-air courtyard for a three-hour Bocce Tournament hosted by Chicago's American Bocce Co. Each player will be offered a curated selection of seasonal craft beers to usher in the fall weather. Grab your fall sweater and your quarantine pod (think of a fun team name) for some fun spirited competitive Bocce play on Oct. 24 and 25. The Bocce Pros will guide your team through a bracket style tournament - enthusiasts and beginners are welcome, no prior experience needed. Group tickets for four are available here for $275 per team: 
  • Artifact Events is hosting the Metropolis Oboe Quartet for the trip of a lifetime during their concert, “We All Need a Vacation!” The voyage around the world starts in Austria with Mozart, before heading to a tango in Argentina, an Italian oboe concerto, Israel for the world premiere of Lee Kesselman’s “Hebrew Meditations,” and finally the English countryside for EJ Moeran’s “Fantasy Quartet.” On Sunday, Oct. 18, cocktails and the visual art display start at 2 p.m. before the concert begins at 3 p.m. Tickets are available for $35 per person HERE.

The Dearborn

The Dearborn Tavern is excited to officially welcome autumn this month with a variety of new, exciting offerings and programming at the restaurant. 

Pastry Chef Julianna Westor is kicking off fall with an elevated take on an essential dessert:  Pumpkin Pie. Available with 24 hour advance notice, diners can enjoy a whole Pumpkin & Vanilla Marble Cheesecake pie featuring cinnamon-graham cracker crust, vanilla and pumpkin cheesecake swirl, and sour cream custard topping for $30. Guests can pre-order by calling the restaurant at 312-384-1242, for dine-in or carryout. 

This month, The Dearborn proprietors, Clodagh and Amy Lawless, are part of the 16 Chicago women restaurateurs presenting “FLAVOR,” a series of collaborative four-course menus on Fridays and Saturdays throughout October. Guests can enjoy the menu highlighting French cuisine & local regional ingredients, including: The Dearborn’s Charcuterie Plate, which features country pâté & chicken liver mousse; a Ham & Raclette Danish from Genie Kwon of Kasama; Coq au Vin with seasonal mushroom and housemade linguine from Bistronomic; and an Upside-down Roasted Financier with apple cider caramel, candied almonds & quatre épices spiced whipped cream from Dana Cree of Pretty Cool Ice Cream. The menu titled ‘A Phenomenal French Affair’ is available for pre-order via TOCK here. ‘Let’s Talk” is an alliance of women restaurateurs, founded three months ago by Vermilion owner Rohini Dey to enable women to get to know each other, support each other, share resources and undertake collective action.

In honor of Election Night Nov. 3rd, The Dearborn is offering a special dinner package full of comfort food you can look forward to — available for carry-out or delivery for while you’re at home anxiously watching the coverage. For $75, guests will be able to pick their favorite two Dearborn tavern style pizzas, plus one old fashioned mac n cheese, 12 secret recipe Dearborn Chicken Wings served with celery and blue cheese dressing, and six patriotic USA themed frosted cookies. 

Finally, to celebrate October’s National Pizza Month, The Dearborn will offer a new speciality pie every weekend throughout the month. 

The Dearborn is located at 145 N. Dearborn St., on the corner of Dearborn and Randolph streets in Chicago’s downtown theatre district. Hours are 11:30 a.m. to 8:30 p.m. Monday through Thursday, 11:30 a.m. to 10 p.m. Friday, 3 p.m. to 10 p.m. Saturday and 3 p.m. to 9 p.m. Sunday. The team has plans to add weekend brunch service later this summer.

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A dynamic duo of drinks at Recess (Courtesy of Recess)

The Goddess and Grocer

  • The Goddess and Grocer celebrates this spooky season with an assortment of themed cookies for Halloween. Guests can customize their order with options from The Goddess and Grocer’s haunting designs--ranging from pumpkins, monsters, the macabre, and more--or request a dealer’s choice assortment. A selection of cookies will also be available in-stores at its Bucktown, Gold Coast, and River North locations. Minimum orders of six are $5 each and must be made 48 hours in advance. 
  • The Goddess and Grocer is now offering seasonally-inspired dishes, soups, sweets, and drinks. The autumnal specials include fall-forward items like Harvest Kale + Quinoa Bowl with roasted brussels sprouts + sweet potatoes, curry chickpeas, manchego, pepitas, shaved red cabbage, and cilantro lime dressing; Short Rib Grilled Cheese with butterkase cheese, arugula, pickled red onions, and horseradish sauce on a grilled challah; and a selection of hearty soups like Gumbolaya, Thai Corn Chowder, and Butternut Squash. Newly added cafe drinks include a Black Pepper Chai, Pumpkin Spice Latte, and a Hot Apple Cider and featured pastries include the Salted Caramel Chocolate Cupcake and a Pink Ribbon Cupcake, a devil’s food cake with marshmallow, pink buttercream, and a pink breast cancer ribbon. In honor of Breast Cancer Awareness month, The Goddess and Grocer will donate $1 from every Pink Ribbon Cupcake to the Lynn Sage Foundation.
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Get your Halloween-themed treats at The Goddess and Grocer (Courtesy of The Goddess and Grocer)

Hubbard Inn

Haunted Dining in the Dark

  • Select dates Wednesday, October 14 through Sunday, November 15
  • Two seatings at 6 p.m. or 8:30 p.m. 
  • $80 per person 

Chicagoans can get in the Halloween spirit with a Haunted Dining in the Dark experience at Hubbard Inn. Located in Masq on Hubbard Inn’s third floor, guests will be offered a multi-sensory, surprise 3-course meal in total darkness. Guests will choose from a vegan, seafood or poultry chef-driven dinner paired with wine in which they will taste without the sense of sight. Each course will be revealed after diners take their first bite in pitch-black. Haunted surroundings will add an extra thrill to the meal. Tickets are $80 per person and include dinner and wine pairings as well as an amuse-bouche upon entry. For tickets, visit:

Joy District

Halloween Drag Brunch

  • Saturday, October 31 from 11 a.m. to 3 p.m.
  • $30 per person 

Joy District will host a Halloween Drag Brunch on Saturday, October 31 from 11 a.m. to 3 p.m. For $30 per person, guests will be offered a bottomless mimosa or domestic beer package with the purchase of a brunch entree. Dynamic performances will begin at 12 p.m. featuring a cast of some of Chicago drag entertainers including Dida Ritz, Serena Fierce, Gina Belle, Lila Star, Khloe (host), and Ruff ‘n Stuff. There will be a raffle for prizes and a cash giveaway. Space is limited. Email to reserve.

Brunch highlights include a Breakfast Croissant with crisp Applewood smoked bacon, scrambled egg, provolone cheese and Bearnaise on a toasted croissant served with brunch taters ($15), Chicken & Waffles with pearl sugar Belgian waffles, buttermilk marinated crispy chicken breast, maple butter sauce and fresh strawberries ($17), and Breakfast Tacos with pork sausage, scrambled egg, provolone cheese, and chipotle crema in a white corn tortilla served with brunch taters ($15).

The Rambler

Oktoberfest Stein Hoisting Contest

  • Saturday, October 24 at 3 p.m.
  • $5 food and drink specials

Guests are invited to celebrate Oktoberfest at The Rambler on Saturday, October 24 with a “socially distant” stein hoisting contest at 3 p.m. along with $5 specials all evening. The contest is open to anyone 21 and older and is first come, first served to sign up starting at 2:30 p.m. The winner will receive an exclusive Sam Adams cooler. Food and drink specials will include $5 Sam Adams Oktoberfest Half Liter Stein, $5 Brats with grilled onion and sauerkraut, and $5 Jumbo Pretzels.

Halloween Football Spooktacular & More

  • Saturday, October 31, starting at 11 a.m.
  • $5 to $30 specials, $35 drink package

On Saturday, October 31 at 11 a.m., The Rambler will host a Big Ten Football Spooktacular with $5 stadium food specials, $5 Paddy’s Irish Whiskey and Skrewball Whiskey, $16 domestic buckets and $30 mega buckets. Perfect for all the Big Ten action, The Rambler has 20 TVs that will show the games with sound on.

On Halloween night, The Rambler will offer a $35 package from 8 p.m. to 12 a.m. that includes an open bar with choice of draft beer, imports and domestic bottles, call liquor and any one food menu item. The evening will also feature a costume contest for best solo costume (winner receives $100 cash), and best group costume for two to six people (winner receives $200 cash or full refund on package fee). Limited space is available. Tickets can be purchased by visiting their website.

Uvae Kitchen& Wine Bar

Halloween Murder Mystery Wine Dinner at Uvae

  • Saturday, October 31 at 7 p.m.
  • $120 per person

On Halloween, Uvae Kitchen & Wine Bar in Andersonville will partner with The Dinner Detective team to host a four-course Murder Mystery Wine Dinner on on Saturday, October 31 at 7 p.m. Costumes are encouraged and guests will be offered bubbles upon arrival. The dinner is $120 per person and menu highlights include Duck Pâté paired with Terres Blondes Gamay, Seared Scallops paired with Cambria Viognier, Short Rib Wellington paired with La Garrigue Cabernet Sauvignon and more. The complete menu with wine pairings is available upon request. Space is limited. For reservations, visit:

In accordance with CDC and City of Chicago guidelines, the dinner will be socially distanced with no more than 25 guests, no tables over six guests and all tables will be spaced six feet apart. Masks are required when not eating or drinking.


Halloween Special at WhirlyBall

  • Friday, October 30 & Saturday, October 31 starting at 12 p.m.

Guests who visit WhirlyBall in Chicago, Naperville or Vernon Hills during Halloween weekend and book an activity on Friday, October 30 or Saturday, October 31 will receive a special gift to take home featuring festive candy and a bounceback coupon redeemable for two free games of WhirlyBall on their next visit. Customers can choose from activities like Bowling (Chicago & Naperville only) and HyperBowling (Naperville only), LaserTag, Ping Pong, WhirlyBall, Giant Connect Four, and Giant Jenga. 

WhirlyBall in Chicago’s Bucktown neighborhood and Naperville will also offer “Beauty is in the Eye of the Beerholder” custom beer flights. Available now through October 31, guests can enjoy four 5-ounce beer selections for only $5. Customers can design their own beer flight from a choice of 24 rotating craft beers on tap with a focus on local and regional brewers. Highlights include Solemn Oath Death by Viking, 3 Floyds Alpha King, Pipeworks Ninja vs Unicorn, Pollyanna Eleanor, SweetWater 420 Strain G13, Buckledown Fritzicuffs Pilsner, Lagunitas Lucky 13, Bell’s Special Double Cream Stout and more.

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Dine in the dark at Hubbard Inn (Courtesy of Hubbard Inn)

Greater Ravenswood Chamber of Commerce and Ravenswood Neighbors Association

Costume & Candy Caravan | Drive-Thru Trick or Treating! - Saturday, October 21st
Calling all ghouls and goblins! The Greater Ravenswood Chamber of Commerce and Ravenswood Neighbors Association is hosting their very first drive-thru trick-or-treating event on Halloween. The caravan will have 10 total stops along the East and West sides of Ravenswood Avenue with candy and treats for all. All attendees are required to wear masks and must remain in the vehicle. No walk-up trick-or-treating is permitted.

There are two time slots for the caravan: 12pm - 1pm and 1pm - 2pm. Families are asked to only select one time slot. The caravan is $5 per vehicle and registration closes at 12AM on Saturday, October 31st. For more information and to sign up, visit

KOVAL Distillery

Spooky Cocktails Class with KOVAL Thursday, October 29th 
KOVAL is hosting a frightful cocktail class on October 29th at 6:30pm. Class will range from learning the magical addition of smoke to your cocktails, as well as fun twists to classics like a Bloody Manhattan and Gummy Worm Martini. Tickets for the class are $10 and can be purchased here

Commonwealth Barbershop

Free Haircuts for Veterans Day - Wednesday, November 11th
Commonwealth Barbershop is offering free haircuts to US Military Veterans for Veterans Day on November 11th. Appointments can be booked online and to receive a free haircut, guests can use promo code "Veteran" at checkout.


Lillstreet is hosting holiday-themed family workshops through December. The workshops are an opportunity to work together on theme projects and bring laughter, smiles, and great new crafts into your life. All workshops are meant for adults and children to participate together and are priced per person. Various workshops include Soup & Chili Bowls, Halloween Candy Dishes, Autumn Mugs, Mini Menorahs, Punch Pot Santa & Eleves, Family Wheelthrowing Fun, Cookie Plates, and more. To view the selection of workshops and sign up, visit

Spooky Cocktails Class
Take a Spooky Cocktails Class with KOVAL (Courtesy of KOVAL)


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