Shopping Events in Chicago

Check out happening shopping events all around Chicago, IL

Pamper Your Pup Valentine's Day Event

 Sun, 15 Feb at 11:00 am Bosly's Backyard USD 30

Roscoe Village Wine Walk

 Fri, 13 Feb at 05:30 pm Roscoe St from Paulina to Western USD 49 to 61

Spring Vintage & Artisan Fest in Ravenswood presented by Windy City Market

 Sat, 21 Mar at 12:00 pm Artifact Events USD 0 to 9

Pickwick Vintage Show in Chicago | April 2026

 Sun, 19 Apr at 10:00 am Chicago Athletic Association - The Unbound Collection by Hyatt USD 12

Trinket Fest Valentine’s Special

 Sat, 14 Feb at 12:00 pm 1750 N Milwaukee Ave Free

Witch-O-Rama Market & Drag Show

 Sun, 22 Feb at 12:00 pm 3527 W. Grand Ave

2026 Chicago Business & Vendor Fair

 Fri, 27 Feb at 10:00 am Millennium Park Free

$5 Pop-Up Market & Brunch in West Loop

 Sun, 15 Feb at 12:00 pm City Hall (restaurant) - Chicago USD 7 to 39

CIRCLE Foundation's 17th Annual Gala

 Sat, 18 Apr at 05:30 pm Alhambra Palace Restaurant USD 0 to 141

SIP, SPA, SLAY BEAUTY EVENT: February 21, 2026

 Sat, 21 Feb at 11:00 am The Sculpt Spot

Thrifting Market - Support Ukraine and help the planet

 Sat, 07 Feb at 01:00 pm 2848 W Chicago Ave, Chicago, IL 60622-4409, United States

Viva La Mujer 2026 Chicago Market

 Sun, 22 Mar at 12:00 pm 1200 W 35th St USD 0 to 10

A Spooky Valentine’s Shopping Soirée

 Fri, 13 Feb at 03:00 pm The Pleasure Chest Free

Chicago Artisan Market

 Sat, 14 Feb at 11:00 am Artifact Events

Ravenswood Makers Market

 Sat, 14 Feb at 01:00 pm KOVAL Tasting Room Free

GALENTINE’S NIGHT AT THE HOLLY HOUSE

 Thu, 12 Feb at 05:00 pm 2438 N Clark St Free

Be Mine - Valentine's Day Market

 Sat, 14 Feb at 12:00 pm enid Free

Ladies Night Chi: For Girly Girls Only!

 Thu, 19 Feb at 05:00 pm 917 W 18th St Free

SPREAD THE LOVE: VALENTINE'S DAY JEWELRY MARKET

 Sat, 14 Feb at 11:00 am The Center of Order and Experimentation Free

Ilia Galentine’s Day Masterclass — Credo Beauty Bucktown

 Fri, 13 Feb at 05:30 pm Credo Beauty USD 15

ACTV Studio IRL: Vuori Southport x OrangeTheory

 Sun, 08 Feb at 08:30 am Vuori Southport Free

Roscoe Village Wine Walk

Fri, 13 Feb at 05:30 pm 2232 W Roscoe St., Chicago, IL 60618

The Shops - Back To School Edition

 Sat, 01 Aug at 11:00 am Water Tower Place (Level 3 Next to JJill and White House Black Market)

How to Walk In Heels Chicago, IL

 Sat, 07 Feb at 02:00 pm 3140 N Lincoln Ave USD 95

GLOW EVENT: Exclusive K-Beauty Experience

 Sat, 07 Feb at 11:00 am LULU LOUNGE USD 25

Handmade Market

 Sat, 14 Feb at 12:00 pm Empty Bottle Free

The Shops - Juneteenth Edition

 Sat, 30 May at 11:00 am Water Tower Place (Level 3 Next to JJill and White House Black Market)

FREE Community Pop-up Thrift Boutique

 Sat, 14 Mar at 12:00 pm Dunning Branch, Chicago Public Library Free

The Reclaimed Wellness Experience "Galentine's Edition"

 Sun, 08 Feb at 10:00 am 1137 S Delano Ct USD 39 to 87

Chicago Vintage Fest

 Sun, 15 Feb at 12:00 pm 622 W Roosevelt Rd Free

FREE Community Pop-up Thrift Boutique

 Sat, 09 May at 12:00 pm Mindy Blanco: Allstate Insurance Free

FREE Community Pop-up Thrift Boutique

 Sat, 27 Jun at 12:00 pm Chicago Police Department Free

Handmade Personal‑Care Artisan Market

 Sat, 21 Feb at 10:00 am Block House Gallery USD 6 to 11

One Less Lonely Pop Up Event

 Sat, 14 Feb at 09:00 am Solo Salon - Elizabeth USD 7

My Beautiful Fluff vending at Navy Piers Black Maker's Market

 Sat, 14 Feb at 12:00 pm Navy Pier Free

The Shops - Mother's Day Edition

 Sat, 09 May at 11:00 am Water Tower Place (Level 3 Next to JJill and White House Black Market)

ACTV Studio IRL: Vuori Rush Street x V1 Leader Elijah Makonnen

 Thu, 19 Feb at 07:30 pm Vuori Rush Street Free

Leather, Lingerie, and Love

 Sat, 07 Feb at 01:00 pm 324 N Leavitt St Free

GLOW EVENT: Exclusive K-Beauty Experience

 Sat, 21 Feb at 11:00 am LULU LOUNGE USD 25

After Hours Fragrance Consultations

 Thu, 12 Feb at 06:00 pm The Shops at Merz USD 45

Fashion Photography Workshop - Learn Fashion Design (FOR KIDS 14 to 18YO)

 Sat, 20 Jun at 12:00 pm Water Tower Place ( Level 3 at FASHIONBAR) USD 342

Clothing Swap

 Sat, 14 Feb at 12:00 pm 3248 N Pulaski Rd USD 13

Yoga on the Courts + Cocktails

 Sun, 15 Mar at 09:00 am Royal Palms Chicago USD 20

The Chicago Vendor Market

 Sat, 21 Feb at 09:00 am The She Shed Free

Shut Up & Read: Silent Reading Party

 Fri, 20 Feb at 07:00 pm Da Book Joint USD 7

Another Vegan 'Lovers' Market by CVTK

 Sun, 08 Feb at 12:00 pm Emporium Arcade Bar

The Sustainable/Upcycle Fashion Basics 101 [Class] [March]

 Wed, 04 Mar at 04:00 pm FashionBar Headquarters USD 482

Strength In Motion - International Women's Day Event

 Sun, 08 Mar at 06:00 pm HAIBAYÔ USD 0 to 13

FREE Community Pop-up Thrift Boutique

 Sat, 28 Mar at 12:00 pm Onward Neighborhood House Free

Yoga on the Courts + Cocktails

 Sun, 29 Mar at 09:00 am Royal Palms Chicago USD 20

Fashion Photography Workshop - Learn Fashion Design (FOR ADULTS)

 Sat, 07 Feb at 12:00 pm Water Tower Place ( Level 3 at FASHIONBAR) USD 342

Pilsen Vintage Market

 Sun, 22 Feb at 12:00 pm 2317 W 18th St Free

Fashion Photography Workshop - Learn Fashion Design (FOR KIDS 14 to 18YO)

 Sat, 16 May at 12:00 pm Water Tower Place ( Level 3 at FASHIONBAR) USD 342

FREE Community Pop-up Thrift Boutique

 Sat, 25 Apr at 12:00 pm Onward Neighborhood House Free

FREE Community Pop-up Thrift Boutique

 Wed, 11 Feb at 10:30 am 4355 W Diversey Ave Free

The Sustainable/Upcycle Fashion Basics 101 [Class] [June]

 Wed, 03 Jun at 04:00 pm FashionBar Headquarters USD 482

Shut Up & Read: Silent Reading Party

 Fri, 06 Feb at 07:00 pm Da Book Joint USD 7

Macy's State Street Wedding Gift Registry Experience

 Sat, 21 Mar at 12:00 pm Macy's State Street Free

South Loop Doods in Pilsen: Le’ Paws + Cafe Solera

 Sun, 22 Feb at 10:00 am Le' Paws Boutique Free

The Sustainable/Upcycle Fashion Basics 101 [Class] [April]

 Wed, 08 Apr at 04:00 pm FashionBar Headquarters USD 482

The Sustainable/Upcycle Fashion Basics 101 [Class] [July]

 Wed, 01 Jul at 04:00 pm FashionBar Headquarters USD 482

Lux Delight Candle Co. Love & Passion Valentines Day Shopping Extravaganza

 Fri, 13 Feb at 06:00 pm AW Event Rental Space Free

Fashion Photography Workshop - Learn Fashion Design (FOR ADULTS)

 Sat, 11 Jul at 12:00 pm Water Tower Place ( Level 3 at FASHIONBAR) USD 342

The People's Market

 Sun, 28 Jun at 12:00 pm FOOD WEB Space Free

Scavenger Hunt Chicago

 Sat, 28 May at 10:00 am Chicago USD 28

"I LOVE YOU BUT I'VE CHOSEN COMICS" 25% OFF Storewide Sale

 Sat, 07 Feb at 11:00 am 1845 N Western Ave, Chicago, IL, United States, Illinois 60647

CHICAGO REDEMPTION WINTER MUSIC AND ART FEST

 Sat, 14 Feb at 10:00 am 220 E Chicago Ave USD 0 to 13

Fashion Photography Workshop - Learn Fashion Design (FOR KIDS)

 Sat, 21 Feb at 12:00 pm Water Tower Place ( Level 3 at FASHIONBAR) USD 342

Unscheduled Cash4RC Buying Event in Illinois

 Sat, 14 Mar at 03:00 pm Chicago, IL

Yoga on the Courts + Cocktails

 Sun, 01 Mar at 09:00 am Royal Palms Chicago USD 20

Open House: 235 W Van Buren

 Sat, 08 Jul at 12:00 pm 235 W Van Buren St Free