Randolph Street Market Festival, 1341 W. Randolph St., returns to Chicago’s West Loop Saturday, September 26 and Sunday, September 27, from 10 am to 5 pm, for its “Best in Show: Tastemakers Choice for Charity” edition, bringing together more than 200 dealers for what’s been billed as America’s largest and liveliest urban antiques market. Since 2003, the market has drawn shoppers from across the country to its expansive outdoor vendor spaces and air-conditioned Beaux-Arts building, offering a rain-or-shine shopping experience spanning antiques, vintage and indie fashion, fine art, vinyl records, estate jewelry, home décor and global goods, and making it one of the nation’s premier urban antique and vintage shopping destinations.

With more than 200 dealers spread across the market’s outdoor grounds and air-conditioned Beaux-Arts building, shoppers can expect an ever-changing mix of vintage and antique furniture, decorative art, fine jewelry, vinyl records, indie designer fashion, global goods and one-of-a-kind finds from sellers across the country.

This September, the market adds a philanthropic twist with its “Best in Show: Tastemakers Choice for Charity” theme. A panel of 75 judges — well-known interior designers, fashion stylists and tastemakers — will roam the show awarding ribbons to their favorite booths across three categories: Fashion Styling, Interior Decor Styling, and overall Best in Show for standout individual items. Randolph Street Market will make a donation to each judge’s chosen charity in their name. Shoppers can look for the ribbons throughout the show to track down judges’ top picks and uncover some of the weekend’s best hidden-gem finds.

This September’s dealer lineup offers a particularly rich sampling of that variety for collectors and design lovers alike. Standout vendors include:

This Old Book – a wide selection of fun, collectible titles known for their eye-catching covers and quirky finds

Oscar Isberian Rugs – a gorgeous selection of legacy hand-knotted rugs sourced from around the world

Range Rider – the market’s biggest collector and seller of vintage cowgirl fashion and accessories

Lottie Dottie – a curated selection of vintage housewares spanning the 1950s through 1970s

Chicago Costume – a huge variety of vintage costumes representing every era

Doggy Doodles – adorable custom pet sketches drawn while you wait

Industrial Cottage – a master upholsterer showcasing his own line of handcrafted furniture creations

Beyond the shopping, Randolph Street Market Festival delivers a full day of eating, drinking and entertainment in the heart of the West Loop. A full on-site bar keeps guests refreshed with beer, wine, spirits and specialty cocktails, while a rotating lineup of food trucks and local restaurant vendors, including Pink Flamingo Cotton Candy, serves up everything from quick bites to full meals and sweet treats throughout the weekend. Live music plays across both days, from live bands to DJs spinning on the market floor, rounding out a festival atmosphere that keeps shoppers browsing, eating and lingering well past their first lap through the vendor stalls.

The full weekend entertainment lineup for both days includes:

Saturday, September 26

All Day

Poems-While-You-Wait – minstrel poets working on vintage typewriters

Museum of YOU – an artists collective creating custom art onsite, including Darling Homebody, Oddcade Oracle Reading, AnaMae Tarot and custom nail art

Darren on the Violin – performing at the Randolph entrance

Vintage Newspaper – a custom newspaper featuring market guests

Rosemary Fanti Fashion Sketches – in the ballroom from 11 a.m. to 1 p.m.

DJ Dave (House, Inside, Ballroom) – spinning fun covers and pop standards

DJ Crate Digga Hash (Inside Lower Hall) – an immersive artist DJ set

DJ BTiggs (Outside Band Stage) – keeping the outdoor stage moving all day

Band Stage

10am-11:30am: Woodstreet Bloodhounds – bluegrass and country swing with early Grand Ole Opry hits

11:30am-1:30pm: Chicago Rock Exchange

1:30pm-3:30pm: Contrabanda Latin Jazz Band – bringing salsa to the stage

3:30pm-5pm: Maxwell Street Blues Band with Lowreen – authentic Chicago blues

Sunday, September 27

All Day

The Traveling Typist – creating prose on the spot

Museum of YOU – an artists collective creating custom art onsite, including Darling Homebody, Oddcade Oracle Reading, AnaMae Tarot and custom nail art

Darren on the Violin – performing at the Randolph entrance

Vintage Newspaper – a custom newspaper featuring market guests

Rosemary Fanti Fashion Sketches – in the ballroom from 11 a.m. to 1 p.m.

DJ Dave (House, Inside, Ballroom) – spinning fun covers and pop standards

DJ Crate Digga Hash (Inside Lower Hall) – an immersive artist DJ set

DJ BTiggs (Outside Band Stage) – keeping the outdoor stage moving all day

Band Stage

10am-12pm: Tony Morrison Jazz Quintet with vocalist Robin Watson – a Frank Sinatra tribute set with mimosas

12pm-3pm: Feel Good 80’s and Classic Dance Covers

3pm-5pm: Michelle Billingsly – channeling the bravado of Nancy Sinatra

Randolph Street Market Festival takes place Saturday, September 26 and Sunday, September 27 from 10 am – 5 pm both days, rain or shine, at 1341 W. Randolph St. in Chicago’s West Loop. Tickets are $14 online in advance and $15 at the door, with discounted admission available for students, military and first responders ($5) and seniors 65+ ($10); children under 12 are always free. Group packages and additional discounts are available online. For tickets, vendor lists and more information, visit www.randolphstreetmarket.com and follow along on social media @randolphmarket.

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Tags: Chicago, near west side, Randolph Street Market Festival