Halloween Events and Date Ideas in Chicago

Halloween Events and Date Ideas in Chicago

Whether you’re dressing up in a couples costume or looking for your other half, Halloween is one of the best nights of the year in Chicago.

I’ve celebrated at private parties where we all dressed up as witches or warlocks. I’ve also gone bar hoping. And I usually end up going to book club’s scary movie night.

Whether you’re more into tricks or treats, here’s a round-up of events and some date ideas for Halloween in Chicago 2021. Here’s hoping it’s not snowing. That’s the scariest thought of them all.


Bites, Babes, Bachelors & Boo’s: A Singles Mingle

Chicago Burger Bible recently started throwing singles mixers and this time she has a special Halloween theme at Whiskey Business. Tickets includes food, and a special shot, plus some non-dorky Halloweenie activities.

Menu will have burger sliders and fries (because duh), but will also be classy with some chicken sliders and the ‘Sex and Candied Cauliflower’ . Costumes are not necessary – but if you want to wear one – have at it!

Get your tickets here: https://ticketstripe.com/CBBsinglemingle1027

Halloween Singles Mixer


Vikings-Themed Halloween Bash at The Graystone Tavern

  • Sunday, October 31
  • $5 to $25 drink specials

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. Table reservations are strongly recommended.

Location: 3441 N Sheffield Ave. Chicago, IL 60657 | (773) 666-5450 | www.graystonetavernchicago.com


Halloween Monster Bash & More at The Rambler 

  • Saturday, October 30
  • $5 to $20 specials; $40 party package

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 are encouraged by emailing events@theramblerchicago.com.

The Rambler Kitchen and Tap Photo: Windy City Cosmo

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 www.theramblerchicago.com. Reservations are encouraged by emailing events@theramblerchicago.com.

Location: 4128 N Lincoln Ave. Chicago, IL 60618 | (773) 799-8881 | https://theramblerchicago.com


Rewired Dresses as “Dominoes” for Halloween

  • Thursday, October 21 through Sunday, October 31
  • $9 to $24 themed food specials 

I just went on a great fall date night at Rewired Pizza Cafe & Bar in Edgewater and it was so fun and honestly delicious. They are 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.

Rewired Photo: Windy City Cosmo

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 enjoy an Orange Creamsicle Slushie cocktail along with other cocktails inspired by old school chains. 

Location: 1100 W Thorndale Chicago, IL 60660 | (773) 360-1621 | www.rewiredcafe.com


Photo: Uvae

Halloween Murder Mystery Wine Dinner at Uvae

  • Sunday, October 31 at 6 p.m.
  • $138 per person

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 enjoy dinner and show will they dine on a five course menu with wine pairings.

Photo: Uvae

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 https://tinyurl.com/yfhywj5x.

Location: 5553 N Clark St  | Chicago, IL 60640  | 773.654.1432  | 



Halloween Family and Adults-Only Costume Parties at WhirlyBall

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 www.whirlyball.eventbrite.com.

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 will enjoy 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.

Photo: Whirlyball

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: Whirlyball
Amanda Whitfield
Amanda Whitfield

Amanda Whitfield is a writer and speaker and a relationship builder. She believes that meeting people in person is important. After attending numerous fashion, startup, and creative events, she founded Windy City Cosmo is 2015 to help people make connections in the city as they build their businesses, start and end relationships and see and be seen. Over the past three years, the entrepreneurs she’s interviewed have become the most successful in Chicago and Windy City Cosmo won an award in 2017 for her work for female entrepreneurs.

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