Lifestyle Events in Chicago

Check out happening lifestyle events all around Chicago, IL

2025 Chicago Top Shelf Tequila and Whiskey Tasting Festival (Sept 27) AE

 Sat, 27 Sep at 02:30 pm Downtown Chicago USD 25 to 89

Jerk, Seafood & Vegan Fest (JSVFest)

 Sat, 20 Sep Union Park (outside)- Chicago West Loop USD 10 to 65

Chicago St Patty Day Exotic Paintings BYOB Wine and Paint Male Model

 Fri, 10 Oct 5425 W Lawrence Ave USD 34

Tune-Up and Turnout: A Back-to-School Bike Ride

 Sun, 17 Aug at 11:00 am Stone Temple Baptist Church Free

JSVFest (Jerk, Seafood & Vegan Festival)

 Sat, 20 Sep at 12:00 pm West Washington Boulevard USD 12 to 535

Wine Crawl Chicago - Be a Tourist In Your Own Town

 Sat, 13 Sep at 01:00 pm TBD Free

Poetry Night at The Walk In

 Wed, 27 Aug at 08:00 pm The Walk In Free

Taste the Movies - Ratatouille (2007) 7 Course Immersive Dinner & Movie Experience

 Fri, 15 Aug at 05:30 pm The Drake Hotel (140 E Walton Pl, Chicago)

Pawlooza Chicago

 Sat, 23 Aug at 01:00 pm 1140 N Wells St Free

Le Dîner en Blanc Chicago

 Thu, 21 Aug at 07:00 pm Chicago

Real Housewives All-Stars Edition Trivia Night!

 Thu, 21 Aug at 07:00 pm Cultivate by Forbidden Root USD 18 to 23

West Town Night Market

 Thu, 21 Aug at 04:00 pm Midwest Coast Brewing Company Free

Adults Night Out: The Rewilding�

 Sat, 06 Sep at 06:30 pm N Cannon Dr at W Fullerton Pkwy, Chicago, IL, United States, Illinois 60614

Slow It Down Sundays “R&B in Pink”

 Sun, 17 Aug at 04:00 pm VU Rooftop Bar USD 0 to 351

2025 Chicago Top Shelf Tasting Festival: Tequila vs Whiskey (Sept 20)

 Sat, 20 Sep at 02:30 pm Downtown Chicago USD 0 to 440

Wicker Park Walking Tour

 Sun, 17 Aug at 03:00 pm Damen Blue Line USD 0 to 45

Half Magic x Ulta Beauty in Chicago, IL

 Sat, 25 Oct at 11:00 am Ulta Beauty Free

Above & Beyond

 Thu, 21 Aug Huntington Bank Pavilion at Northerly Island

Single N Minglin “Speed Dating Event “

 Sat, 23 Aug at 09:00 pm Privilege Restaurant Bar USD 26 to 38

Paint Nite Brand Creative Events

 Sat, 16 Aug at 12:00 pm Output Lounge USD 42

Single N Minglin “Speed Dating Event “ (AGE: 50 Plus Event)

 Sat, 13 Sep at 09:00 pm Privilege Restaurant Bar USD 26 to 38

Singles Events Ages 32-44 | Chicago Speed Dating | Speed Chicago

 Sun, 17 Aug at 06:00 pm Recess USD 39

Green City Market's 2025 Chef BBQ

 Thu, 04 Sep at 06:30 pm South End of Lincoln Park USD 37 to 659

Single N Minglin “Speed Dating Event “

 Sat, 27 Sep at 09:00 pm Privilege Restaurant Bar USD 26 to 38

CareFreeBlackGirl CookOut Chicago

 Sat, 30 Aug at 02:00 pm Park No. 540 USD 13 to 50

PUFF & PAINT

 Sat, 23 Aug at 07:00 pm GLOW UP CREATIVE ARTS STUDIO USD 45 to 82

Meet IRL | Friday Night Singles Mixer | Ages 25-35

 Fri, 22 Aug at 06:30 pm Verve Wine USD 29 to 39

Uncle Charlies R&B Cookout at Huntington Bank Pavilion at Northerly Island

 Sat, 06 Sep Huntington Bank Pavilion at Northerly Island

Marcus Bailey

 Fri, 15 Aug at 06:00 pm Cubby Bear

BXVL Market - Slider Fest

 Wed, 10 Sep at 04:00 pm Boxville Free

Reba Meyers

 Fri, 15 Aug at 06:00 pm Cobra Lounge

Latina Expo 2025 – Chicago | Empowerment, Innovation & Community

 Fri, 03 Oct at 09:00 am Malcolm X College USD 14 to 26

Lux Life Realty Anniversary Celebration

 Sat, 30 Aug at 12:00 pm The Robey Free

Sapori Presents Benzinger Wine Dinner

 Wed, 10 Sep at 06:30 pm Sapori Trattoria USD 109

Summer Dance Work Out

 Sat, 23 Aug at 11:00 am Dvorak (Anton) Park Free

Saturday Night Ages 25-39 | Chicago Speed Dating | Speed Chicago

 Sat, 16 Aug at 07:30 pm Time Out Market Chicago USD 44

Homemade Pasta Class - Fresh Pasta Carbonara

 Fri, 22 Aug at 06:30 pm Bettie's Chicago USD 151

Perfect Catering 2nd Supper Club

 Fri, 29 Aug at 07:00 pm 2529 N Milwaukee Ave USD 45

Ashley Gavin

 Fri, 22 Aug at 06:00 pm Vic Theatre

Pups & Palomas

 Sat, 23 Aug at 02:00 pm Somerset Patio Free

Solo Crowd Presents: You Only Live Once More

 Fri, 22 Aug at 09:30 pm The Newport Theater Free

Saturday Night Ages 25-39 | Speed Dating in Chicago | Speed Chicago

 Sat, 23 Aug at 07:30 pm Tabu USD 44

Mentors Who Run x RunTooHard - Humboldt/606

 Sat, 23 Aug at 08:00 am Drink happy thoughts Humboldt Free

✨ Amor y Picnic ✨

 Sun, 24 Aug at 12:00 pm Harrison Park Free

Hands-On: Gnocchi al Pesto

 Fri, 12 Sep at 06:00 pm Eataly Chicago USD 103

Buckle Up: Traditional belt making meets modern hands

 Sat, 16 Aug at 02:00 pm Dream Creeks - Artisanal Leather Goods and Workshops USD 71

Mini Wellness Expo with Emily Bond

 Sat, 16 Aug at 01:00 pm Passages Wine and Books USD 0 to 20

Paint Nite Brand Creative Events

 Sat, 23 Aug at 12:00 pm Output Lounge USD 42

Speed Dating in Chicago (Ages 24-36) | Speed Chicago | Singles Events

 Thu, 11 Sep at 07:00 pm Untitled Supper Club USD 39

Hands-On: Pasta Traditions from the South

 Sat, 30 Aug at 04:00 pm Eataly Chicago USD 103

Gen X Dance Party

 Sat, 20 Sep at 06:00 pm Biagio Events "Jada" Room USD 44

Sábado en la Plaza

 Sat, 16 Aug at 12:00 pm 1701 W 18th St Free

Saturday Night (Ages 25-39) | Speed Dating in Chicago | Speed Chicago

 Sat, 30 Aug at 07:30 pm Time Out Market Chicago USD 44

The California Honeydrops

 Sat, 27 Sep at 06:00 pm Thalia Hall

Dorothy

 Tue, 16 Sep at 06:00 pm House Of Blues - Chicago

The Collective Unified Presents: RUNWAY

 Sun, 17 Aug at 07:00 pm HOKA Chicago, IL Free

Chicago Speed Dating (Ages 25-39) | Speed Chicago | Saturday Night

 Sat, 13 Sep at 07:30 pm Time Out Market Chicago USD 44

BYOB Paint and Sip Event - “Colorful Lion"

 Sat, 16 Aug at 07:00 pm Sip & Paint USD 43

CHICAGO HALLOWEEN BAR CRAWL - 10+ Bars - Nov 1st

 Sat, 01 Nov at 07:00 pm Wrigleyville USD 19 to 35

Ground & Sound - A Courtyard Yoga Experience

 Sat, 16 Aug at 09:00 am Waldorf Astoria Chicago USD 82

Bend Over Buddy

 Fri, 22 Aug at 07:00 pm The Pleasure Chest Free

Singles Events (Ages 24-36) | Chicago Speed Dating | Speed Chicago

 Thu, 25 Sep at 07:00 pm Untitled Supper Club USD 39

Drink & Draw

 Mon, 18 Aug at 07:00 pm Beermiscuous Free

3238 WINE TASTING CLASS-BECOME A WINE CONNOISSEUR:

 Fri, 15 Aug at 07:00 pm Discovery Center USD 42

Yoga on the Patio at Kirkwood Bar

 Sun, 24 Aug at 09:45 am Kirkwood Chicago Free

Speed Dating in Chicago (Ages 25-39) | Speed Chicago | Saturday Night

 Sat, 06 Sep at 07:30 pm Tabu USD 44

Peephole

 Fri, 29 Aug at 06:00 pm Cubby Bear

Leatherworking Workshop: Make Your Own Leather Wallet

 Sat, 30 Aug at 02:00 pm Dream Creeks - Artisanal Leather Goods and Workshops USD 135

Mayambo Summer Gala

 Sat, 16 Aug at 09:30 pm Dance Center Chicago

Willi Carlisle

 Sat, 27 Sep at 06:00 pm Lincoln Hall

Dine Out On Broadway

 Fri, 15 Aug at 03:00 pm Dine Out on Broadway

Ceramadicks: DIY Dildo Workshop

 Fri, 22 Aug at 07:00 pm Pink Giraffe Art Studio USD 32

All White Attire R&B Vs House RoofTop Party @ Vu (Chicago)

 Sun, 31 Aug at 05:00 pm VU Rooftop Bar USD 18 to 962

Chicago Style Deep Dish Pizza Making Class

 Thu, 28 Aug at 06:30 pm Bettie's Chicago USD 146

Christmas Wonderland Mini Photoshoots | Chicago, IL

 Sat, 27 Sep at 10:00 am Chicago, IL

Dinner & Dancing: Tapas Making Class & Dancing Lessons!

 Fri, 15 Aug at 07:00 pm Get in the Kitchen USD 97

Colony House VIP Experience // Chicago, IL Sept 19

 Fri, 19 Sep at 05:30 pm Thalia Hall USD 66 to 189

The Sister Circle of Chicago Launch Tea Party

 Sun, 24 Aug at 06:30 pm Connect Gallery Free

Randa Rose: Disco Dreams & Designer Things

 Sun, 17 Aug at 12:00 pm Good Night John Boy USD 36 to 1,705

Ky Newman at The Outset

 Sat, 20 Sep at 10:00 pm The Outset

The Market Shop: Summer Reset Edition Weekend 1

 Sat, 16 Aug at 10:00 am Time Out Market Chicago Free

Sourdough for Beginners with Baker Bettie

 Sun, 17 Aug at 10:30 am Bettie's Chicago USD 242

TW Training x Summer House Cookie Run

 Sun, 24 Aug at 09:15 am Summer House Santa Monica Free

Picnic & Paddle w/ Lathrop Ambassadors (Fall Session)

 Sat, 27 Sep at 03:30 pm Lathrop Boathouse Free

Cheese 101: Guided Italian Cheese Tasting

 Thu, 28 Aug at 05:30 pm Eataly Chicago USD 66

Modern Fiction Lilliput Bookclub in August: Bel Canto

 Tue, 26 Aug at 06:30 pm Lilliput Books Free

Elevated Evenings: 6-Course Infused Dinner Party Experience

 Sat, 16 Aug at 07:00 pm Prohibition THCafe USD 143

DIY denim painting workshop

 Fri, 15 Aug at 07:00 pm Luvsick Plus USD 60

FRIDAYZ- Afrobeats, Amapiano, Dancehall At Masada

 Fri, 15 Aug at 09:30 pm Masada USD 0 to 215

The Social Chef - Craveable China Session 2

 Sun, 24 Aug at 04:00 pm 215 W Washington St USD 85 to 160

Shut Up & Read: Silent Reading Party

 Fri, 22 Aug at 07:00 pm Da Book Joint USD 7

Ohenewaa’s AfroBrunch Series

 Sun, 17 Aug at 01:00 pm 1125 W Van Buren St USD 66 to 77

Salsa in the Sky

Sat, 16 Aug at 05:00 pm 210 N Racine Ave, Chicago, IL, United States, Illinois 60607

Cocktail Happy Hour

 Fri, 22 Aug at 06:00 pm WineStyles Chicago Free

SATURDAYZ @ MASADA - Afrobeats, Amapiano, Dancehall

 Sat, 23 Aug at 10:00 pm Masada USD 0 to 189

Own it Experience Beginner Chair Dance & Kava Ceremony

 Sat, 16 Aug at 07:00 pm Wildlight Yoga USD 34

WHITE & SILVER (Grown & Sexy) PARTY

 Fri, 15 Aug at 09:00 pm Row 24 Chicago USD 0 to 355

An Exploration of the Willamette Valley

 Tue, 19 Aug at 06:00 pm Grand Cru Chicago USD 60

SATURDAYZ @ MASADA - Afrobeats, Amapiano, RnB, Dancehall

 Sat, 16 Aug at 10:00 pm Masada USD 0 to 189

Weekly Wine Tasting

 Thu, 21 Aug at 06:00 pm WineStyles Chicago USD 13