By GINNY VAN ALYEA

As we head into another Memorial Day weekend, thoughts will be on summer art hallmarks like some of the city's longest running art fairs and markets, several of which have been taking place for decades. Each weekend is an opportunity to travel around the city and spend time in its neighborhoods being a part of these traditions and creative gatherings.

View CGN's full calendar of events taking place all summer long. More events, including art fairs and festivals will be added each week.

Randolph Street Market – May 24 & 25 in West Loop

The Randolph Street Market opens in the West Loop on Saturday May 24 and runs on Sunday the 25th as well. The summer market takes place outside as well as inside of Plumber's Hall, making for a true treasure-hunting expanse. Open 10am to 5pm both days (with a charity preview on Saturday at 9am) the 2025 Garden Party features 200 sellers offering the best vintage, antique & repurposed furniture, art, decor, ephemera, vintage fashion and global goods. Tariffs be damned! There's also continuous live music & DJ’s as well as fun food and libations to keep the party going and the wallet open...

This year RSM founder Sally has gotten extra creative and there are festive ticket packages for families (drinks for adults, snacks for kids) as well as outings with your girlfriends (Prosecco for everyone!) and for students (cheap tickets that mean you can buy your own drink!)

May 24 and 25

1341 W Randolph St

Indoor & Outdoor

Details

57th Street Art fair – June 7 & 8 in Hyde Park

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Kick off the summer at the first major art fair of the season, located in the beautiful Hyde Park neighborhood on the South Side of Chicago. The 57th Street Art Fair is THE place to buy art, whether you’re a seasoned collector or new to the art scene.

Listen to some of Chicago's best Blues music at the Buddy Guy's Legends Stage, meet friends, bring your family, enjoy the day at this historic, welcoming, fun event. All artists exhibiting at the Fair are stationed in their booths throughout the weekend to discuss their work.

Saturday, June 7, 11–6 and Sunday, June 8, 10–5

Admission is always FREE

Gold Coast Art fair – June 7 & 8, Downtown

Amdur Productions puts on a nonstop run of art fairs in the city and the suburbs from Memorial Day onward (view full schedule here)

During the first weekend in June the long-running Gold Coast Art Fair marks its 67th year and returns to Chicago’s Grant Park. Featuring over 200 juried artists from across the country, with a diverse range of original works in painting, sculpture, jewelry, ceramics, mixed media, and more, thousands of visitors are expected.

Set in the heart of Chicago, between the Art Institute and Lake Michigan, the Gold Coast Art Fair offers an exciting atmosphere with live music throughout the weekend, and a variety of food, wine, beer, and sangria at three oases in Grant Park’s Butler Field. The fair also includes Paint and Sip classes, henna art, caricatures, personalized poems, and interactive art booths for kids. The Kids Art Zone is packed with fun activities, including face painting, sand art, giant bubbles, and more.

Saturday, June 7 and Sunday, June 8, 10a-5p daily.

Tickets are $15, with $2 from each sale benefiting WINGS Program, Inc., a non-profit organization dedicated to providing housing, integrated services, education, and advocacy to end domestic violence. Children 12 and under are admitted free.

Fox River Arts Ramble, June 7 & 8 in St, Charles

The Fine Line Creative Arts Center invites you to The Fox River Arts Ramble, a one-day ramble through the Fox River Arts area, showcasing the amazing art and artists in this creative community west of Chicago. Fine Line's ever-popular Outdoor Artisan Market will feature new and returning artists, live music, and art demonstrations. Riverlands Brewing Company and Inches Taco Truck will offer great beer and great food! There is a music lineup and there will be dozens of local artists offering affordable art.

Saturday, June 7, 10 am - 4 pm

St. Charles, IL

No Admission Fee. Includes the Fine Line Art Festival.

Open Rain or Shine

Old Town Art Fair - Jun 14 & 15 in Old Town

Chicago’s legendary Old Town Art Fair, now celebrating its 75th Anniversary, returns to the heart of the historic Old Town Triangle Historic District the second weekend in June. Established in 1948, the Old Town Art Fair is one of Chicago’s oldest juried art fairs and one of the first fine art fairs of its kind in the country.

Organized by the non-profit Old Town Triangle Association and completely volunteer-run, this year’s Fair will be the most festive in its milestone 75-year history, attracting over 230 artists from across the country plus live music on two stages; an array of classic Chicago food and beverage options from local vendors; a dedicated Children’s Corner featuring interactive activities and crafts for kids; and the return of self-guided Garden Walks in over 50 gardens in the Old Town Triangle neighborhood. Annually, the Fair introduces artists to an estimated 30,000 art lovers over the course of the two-day event. 

Chris Nelson, Old Town Art Fair 2025 Chair, noted that a record number of artists applied to exhibit this year. “We have world class artists across all media showing with us,” he said. “We continue to expand our search for new exhibitors to ensure talented contemporary and upcoming artists are well represented, bringing a fresh feel to each year that has contributed to the Fair’s longevity and legacy over the past 75 years. From exceptional art to strolling Old Town’s historic gardens, there will be something for everyone to discover in this year’s Fair!”

Along with the visual art offerings, the Garden Walk--an attendee-favorite year after year--offers visitors the opportunity to tour over 50 gardens, many of which are private and only viewable during the Art Fair. Organizers provide historical information, fun facts, and anecdotes about the homes, architecture, and past and present residents. Old Town’s quaint green spaces make the neighborhood a charming and delightful destination for locals and tourists alike. 

Proceeds from the suggested donation of $12 for adults (free for children) go directly back into local schools, arts, and cultural programs in the area, including historic and architectural preservation clubs; the Menomonee Club; and the Old Town Triangle Association.

Saturday, June 14, 10am-7pm, and Sunday, June 15,10am-6pm.

OldTown Triangle Historic District - Main Gate at the intersection of Lincoln and Wisconsin Streets

Takes place, rain or shine

Art Fair on the Square, Jul 12 and 13, Madison, WI

One of the Midwest’s most popular and highly regarded outdoor celebrations of the arts will return to the Capitol Square on Saturday, July 12 and Sunday, July 13, 2025, as MMoCA presents the 67th annual Art Fair on the Square.

With its mix of music, entertainment, and outdoor dining, as well as over 500 artists exhibiting paintings, prints, photographs, sculpture, jewelry, handmade clothing and accessories, and fine craft, the fair draws nearly 200,000 visitors to Madison’s Capitol Square.

Madison, WI

Saturday, July 12, (9 AM–6 PM)

Sunday, July 13, (10 AM–5 PM)

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View CGN's full calendar of events taking place all summer long. More events, including art fairs and festivals will be added each week.