Halloween at Kit Kat Lounge features fabulous events for dining and drinking. On Saturday, Oct. 27, it's a 'Little Shop of Horrors' brunch followed by a "Once Upon a Time" dinner. The staff will be dressed as "Once Upon a Time" fairy tale characters, living out their fantasies and Kit Kat's mixologists will serve a bevy of creative and creepy fall cocktails, including the Black Widow, Hpno-Haunt and Voodoo Diva. On Sunday, they go all Rocky Horror for brunch. Then on Halloween, the staff will channel "Dead Presidents" just in time for election season. Guests at either party are invited to dress in the same theme or as anything they'd like - but go all out as the best costumed person will receive $300 in cash, and the runner up will receive a gift basket worth $250. Kit Kat's Divas will also dress the part and entertain the crowd.
Brown bagging your lunch downtown on Daley Plaza from Friday, Oct. 26 through Oct. 31 will find you in the middle of "FrankenPlaza". Midnight Circus will be performing stunts, dances and crazy comedy to entertain you.
Throw on your spookiest Halloween costume and join the Green City Market Junior Board for its Halloween Harvest Ball at Ravenswood Event Center on Sunday, October 28 from 4p.m. to 8p.m. The ghoulish event will feature many of Chicago's top chefs, pastry chefs and mixologists offering seasonal bites and drinks utilizing products from Green City Market farms. Tickets are $75, $65 for Friends of the Market.
A Chicago Avenue Halloween bar crawl starts at 8pm on Saturday, Oct. 27with three participating locations offering $3 Jameson shots and $4 select craft pints. The first official stop is at Cleo's at 9 p.m. Cleo's (1935 W. Chicago) with $100 in cash for the best Halloween costume at 10:30pm. The second stop is Roots Handmade Pizza at 10:30pm. With a $100 in cash for the best Halloween costume at midnight. The evening winds up at High Dive with a contest for the best Halloween costume, $100 in cash prize, at 1:30am.
Lottie's and The Pony are co-hosting a haunted house bus trip to Statesville Haunted Prison on Thursday, Oct. 25. After registration at both locations, the $40 per person package includes one hour of domestic drafts, transportation to Statesville Haunted Prison on a coach bus (with refreshments) and haunted house admission.
The Black and Boo Halloween Pawty on Sat., Oct. 13 at Durbin's 17265 Oak Park Ave. in Tinley Park is a benefit for Lulu's Locker Rescue. The $45 ticket includes dinner, premium open bar, raffles, door prizes, themed activities and DJ music till 11 p.m.
"Boneshaker" on Saturday, Oct. 27 at Redmoon Central features large-scale spectacles and performances, music by live bands The Talking Deads and Wild Jesus and DJs White Russian and Chaz Vrba, plus cocktails and a pancake breakfast by Babycakes food truck for $50.
Orso's in Old Town's Halloween Bash on Sat., Oct. 27, $20 in advance $25 at the door, includes with a costume contest, unlimited wine and beer until midnight and music by DJ Ruben Chilly.
Not really Halloween themed, but since one of the joys of early autumn is the abundance and variety of freshly harvested apples, Benny's Chop House is celebrating National Apple Month by serving a unique and delicious version of the all-American dessert, a beautiful Michigan Apple Tart ($9.99).