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- Daily Email - Monday - 10/20/2025
Daily Email - Monday - 10/20/2025
At some point, Halloween stopped being about candy and became a month-long marathon with dressing up and themed cocktails. And honestly? We support it. From drag brunches to haunted parades, the city’s full of ways to scare hot and party harder. Here’s your game plan.
What if you could enjoy bottomless brunch and serve final-girl realness at the same time? Enter to win tickets to this horror-themed drag brunch, where the queens slay harder than Freddy. Enter if you dare.*
JUST ANNOUNCED
Raise a glass, Maple & Ash is celebrating a decade of unforgettable wines! Join them on October 25th for Taste the List, a curated tasting of award-winning bottles and rare gems. Be part of this milestone evening and enter to win free tickets.*
Kindred the Family Soul brings smooth harmonies and heartfelt energy to Chicago. Feel the love live, we’re giving away 2 tickets to this soulful night. Enter now to win.*
Grizzly Bear returns to The Salt Shed on November 9th with lush harmonies, layered soundscapes, and indie perfection. Experience their mesmerizing live show in one of Chicago’s most stunning venues. Enter to win tickets now.*
The energy is wild, the paddles are fast, and yes, it’s pretty hardcore. Major League Table Tennis hits Chicago for week 4 of their national series, and it’s weirdly intense in the best way. Win a 4-pack of courtside tickets.*
DATE NIGHT IN CHICAGO
Photo: Garfield Park Conservatory Facebook
Do you play it safe with the usual go-to, or try to impress with something spicy and unhinged? Either way, date night in Chicago has range. If planning is stressing you out (or your last idea involved another brewery), we got you.
COOKIES CANNABIS DISPENSARY PRESENTS:
$250 BALLER BAG | OCTOBER GIVEAWAY
Cookies Chicago isn’t just a dispensary, it’s a whole vibe. And right now, they’re giving away a $250 Baller Bag to one lucky text and email subscriber. Enter by October 31st to win. No purchase necessary. Must be 21+ w/ valid ID. Find Cookies at 215 N. Clinton St., West Loop, steps from Union Station.*
EVENTS TO LOOK OUT FOR
🖋️ The Living Canvas
Saturday, November 1st at SevenStar Vanue (5PM)
See tattoo artistry elevated to the max. The Living Canvas is a curated gallery night featuring Chicago’s top tattoo artists, live models, music, food, and giveaways, including free tattoo time! Win tickets for the experience.*
🎃 The Nightmare Before Christmas In Concert
Saturday at Auditorium Theatre (7:30PM)
The Chicago Philharmonic plays Danny Elfman’s iconic score live while Jack Skellington spirals on screen. Come in costume, and relive the classic. Halloween, but make it orchestral. Enter to win tickets to the upcoming philm.*
🍸 Pillow Talk: A Showgirl Affair
Thursday at Broken Shaker (9PM)
Slip into something comfy, Pillow Talk is settling into Broken Shaker on Thursday . Hosted by Opal, this night blends sultry sounds, soft lighting, and dreamy DJ sets from Jaxx and more. Enter to win a pair of tickets.*
🇬🇧 Michael McIntyre: MACNIFICENT
Friday, April 17th at The Chicago Theatre (8PM)
Britain’s biggest comedy export, Michael McIntyre, lands at The Chicago Theatre with a brand new tour. Expect high-energy chaos, face-cramp laughter, and at least one bit about his kids. Enter to win tickets to catch him live.*
🔥 Akaash Singh
Friday, April 24th at The Chicago Theatre (7PM)
Akaash Singh is bringing his razor-sharp takes and rapid-fire comedy to Chicago this April. The Generational Triumph Tour hits The Chicago Theatre on April 24th. Enter to win a pair of tickets and laugh your ass off.*
FEATURED CALENDAR
 | TOM 10/21 • Los Fabulosos Cadillacs THU 10/23 • Lorna Shore FRI 10/24 - SUN 10/26 • My Morning Jacket FRI 10/31 • Lil Tecca SAT 11/1 • Jeff Tweedy WED 11/5 • Little Simz |
LOCALS ONLY
We stopped by Woodie’s Flat to try their latest Malört wings. See our review + enter to win a Malört-themed giveaway.
A pool. A projector. A crowd yelling at the screen. The Rocky Horror Picture Show comes to the Intercontinental this weekend. More here.
This one’s for the makers. A day bringing together Chicago creators at Drip Collective. Plus, it’s free.
Chicago will literally give you donuts, drinks, and free things just for surviving another year. Here's everywhere to milk your birthday for all it's worth.
🎟️ BINGE LIFE!
You read Do312 to know about the best things to DO in Chicago, but are you ready to Do312 MORE???
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Or just keep sitting on your couch, scrolling through streaming sites pretending like you’re going to find something to watch at home on your own, like these two,
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FEATURED
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