18 of the Best Art Galleries in Chicago, According to a Gallery Director, a Local Artist and a Self-Proclaimed Aesthete

Most Famous

• Neighborhood: The Loop
• Key Artists: Vincent Van Gogh, Salvador Dalí, Andy Warhol

The Art Institute of Chicago is not only one of the oldest and largest galleries in Chicago, it’s one of the oldest and largest galleries in the country. So it should come as no surprise that you’ll find some of the world’s most famed pieces inside its walls. Both Grant Wood’s “American Gothic” and Pablo Picasso’s “The Old Guitarist” are on permanent display, and the rotating exhibits tend to feature names that draw big, big crowds: Vincent Van Gogh (through Sept. 4) and Salvador Dalí (through June 12) are currently showing, joining the ranks of previous featured artists like Andy Warhol and Rembrandt. A pro tip? Illinois residents can visit for free in the summer on Thursdays from 5 to 8 p.m.

312-443-3600, 111 S. Michigan Ave., Chicago, IL; 60603; artic.edu

Most Contemporary

• Neighborhood: River North
• Key Artists: Mona Hatoum,  Lotus Laurie Kang, Thomas Schütte

When it comes to contemporary art in the city, the long-standing Museum of Contemporary Art is unrivaled. Featuring works in just about every medium imaginable from the artists of our era, you’re just as likely to see a great photograph here as you are hanging, unfixed photographic film dubbed as a “skin” by artist Lotus Laurie Kang. The city’s residents are also privy to the museum’s Art in Free Spaces initiative, which sees it commissioning site-specific pieces, such as Thomas Schütte’s “Big Spirits XL” sculptures, which reside outside the building.

Best for Exploring New Artists

• Key Artists: Hebru Brantley, Sentrock, lefty OUT there
• Neighborhood: West Town

Both Alonzo and Jados cited Vertical Gallery among their favorite galleries. Now in its tenth year, this urban-contemporary haven in Ukranian Village focuses on “work influenced by street art, urban environments, graffiti, pop culture, graphic design and illustration.” “I love to see the diversity of the artists here,” Alonzo says. “The influence of urban environments and street art has earned its way into the art scene. I have experienced work by artists at Vertical Gallery for the first time and watched them grow and make their footprint in the art world.”

Alonzo cites Hebru Brantley, Sentrock and lefty OUT there as her top picks.

773-697-3846, 1016 N. Western Ave., Chicago, IL, 60622, verticalgallery.com

Most Unique

• Key Artists: Nick Cave, Bob Faust, Ragnar Kjartansson Song
• Neighborhood: River North

According to Alonzo, this is “not your traditional gallery,” and she’s right—it’s actually an art-filled museum and hotel that you can book stays in. Make no mistake, however—the art here is not merely decorative. “We designed the museum for art,” founder Steve Wilson says. With technical installations built into the building (which is open 24/7), like the site-specific video Holding Rhythm projection that features a tiger stalking its "landscape," and 10,000 square feet of exhibition space housing 100 multi-media artworks, this space is one Alonzo loves checking out for the rotating exhibitions, which see walls dressed by Nick Cave and Bob Faust (the pair’s Elevate wallpaper exhibition runs through December 2023). “This is always a happy place for me,” she gushes.

312-660-6100, 55 E. Ontario St. Chicago, IL, 60611, 21chicago.com

Most Diverse

• Neighborhood: West Loop
• Key Artists: Allana Clarke, Esmaa Mahamoud, Suchitra Mattai

Kavi Gupta’s reach goes far beyond the borders of Chicago—Alonzo has stopped at its booths in various exhibitions all over the world. “I am lucky to have this gallery right here in my neighborhood,” she says. “I love seeing who is in the storefront, [even if I don’t] have time to stop in. It is a wonderful space to discover new artists and immerse yourself in culture and art.” Alonzo also appreciates that Kavi Gupta focuses on underrepresented artists and diversity—something she calls “absolutely incredible.”

312-432-0708, 835 W. Washinton Blvd., Chicago, IL, 60607, kavigupta.com

Most Accessible

• Neighborhood: Ukranian Village
• Key Artists: Nicolas Jiminez, Sick Fisher, Karl Jahnke

Putting a stamp on the Chicago art scene in 2011 with its bold, colorful and even macabre pieces, this Chicago Avenue haunt is on a mission to make art accessible. So much so, in fact, it’s been hailed as the “anti-gallery,” with owner Sara Dulkin normalizing everything from buying art online to flash sales that make pieces affordable to the average customer in her hilarious Instagram Reels. “Chicago Truborn has one of the best social media games in the biz, and the gallery is exactly what you would expect—f-ing rad,” Jados says. “[It does] immersive exhibitions that haul you into the artist's world. Art for everyone, at every price point. One of Chicago’s finest, for sure.”

773-420-9764, 1741 W. Chicago Ave., Chicago, IL, 60622, chicagotruborn.com

Most Inviting

• Neighborhood: Wicker Park
• Key Artists: Donald Topp, Howard Finster, Peter Mars

Despite the fact that this intimate space has been bringing art to the masses for more than three decades, having opened in 1991, owner and artist David Leonardis still has plenty of passion—something Jados says is infectious. “His energy and love for art are contagious,” she says. “He can turn anyone into a collector!” As for what to pick up here, Jados points to “old-school artists, like Howard Finster, Matt Lamb and Peter Mars,” as well as “up-and-coming pop artists, like Donald Topp”—aka the guy behind those above-pictured tattooed Disney princesses.

312-863-9045, 1346 N. Paulina St., Chicago, IL, 60622, dlgalleries.com

Best Hidden Gem

• Neighborhood: Logan Square
• Key Artists: Ariel Sinha, JC Rivera, Kayla Mahaffey

“All-Star Press is a Logan Square gem,” Jados says of this all-inclusive print studio, gallery and retail space. “[It features] countless artists…and [fuses] a love for music, film and sports into the art world.”  While sports fans will find plenty of Chicago team-based prints courtesy of artists like JC Rivera (go Bulls),  you’ll also see stunning portraits, like this one of Frida Kahlo by local designer and illustrator Ariel Sinha, pass through its door. “[It’s a] great place to find unique, limited-edition prints and discover new artists,” Jados shares.

773-766-4060, 2775 N. Milwaukee Ave., Chicago, IL, 60647; allstarpresschicago.com

Best Photography

• Neighborhood: River North, Bridgeport
• Key Artists: David Yarrow, Jeff Koons, Paul Nicklen

Photography and film are the key focuses here, with the gallery citing little divide between the two. “They are the most immediate and indelible way to document the history of cultures, of people, of nations and of our planet,” the site reads. The subject matter runs the gamut, however, ranging from iconic models in reimagined settings, à la David Yarrow (Cindy Crawford in the Wild, Wild West, anyone?) to arctic wildlife (Paul Nicklens).

312-475-1788, 716 N. Wells St., Chicago, IL, 60654, hilton-asmus.com

Most Curated

• Neighborhood: River North
• Key Artists: Tyler Shields, Brandon Boyd, Lea Fisher

Alonzo serves as the Gallery Director for Samuel Lynne, a Dallas-based gallery with an in-house art sales division in Chicago’s River North neighborhood. There’s a good chance you’ll recognize a name or two from its heavily curated roster of contemporary artists from the 21st century: The gallery counts Incubus singer Brandon Boyd and celebrity photographer Tyler Shields, once heralded as “the Andy Warhol of his generation” by Sothebys, among them.

312-279-2776, 215 W. Huron St., Ste. 1, Chicago, IL, 60654, samuellynne.com

Most Unconventional

• Neighborhood: Old Town
• Key Artists: Mary Lou Zelazny, Fred Stonehouse, CJ Pyle

With a focus on self-taught, “outsider” artists, or those with few ties to the conventions of the art world, Carl Hammer Gallery yields some mighty interesting finds. In addition to the traditional acrylic oil on canvas, you might come across a sheet of flash tattoos, a set of vintage sideshow banners, a carved and painted wood sculpture or a newspaper print from the New York Times here—the selection is vast and varied. While reviewers say this isn’t the type of gallery you bring your kids to peruse, its wares are unique enough to warrant a trip off the beach River North gallery path.

312-266-8512, 740 N. Wells St., Chicago, IL, 60654; carlhammergallery.com

Best Large-Scale Installations

• Neighborhoods: Streeterville, West Town
• Key Artists: Jaume Plensa, Alex Katz, Torkwase Dyson

With three locations to visit (including one in NYC) and a “globally recognized team of art professionals” working together to develop what the gallery calls “historically important artists” from around the world, the level and range of talent here is broad. Richard Gray doesn’t shy away from larger installations either, so you may see a large-scale exhibit in cast aluminum depicting  a row of heads (Jaume Plensa) or Torkwase Dyson's larger-than-life geometric sculptures next to a painting or drawing by renowned artist Alex Katz. If it’s a special piece in the wild you’re after, the gallery may also be able to use its wide-spanning connections to help you track it down.

312-642-8877, 875 N. Michigan Ave., Ste. 3800, Chicago, IL, 60612; richardgraygallery.com

Most Naturalistic

• Neighborhood: River North
• Key Artists: John James Aububon, Mark Catesby, Abbe Laurent Berlese

Wildlife enthusiasts will go gaga for this fine arts gallery, which focuses on natural history art from the seventeenth and nineteenth centuries. (Read: You’ll find bird, botany and animal prints galore, some of which are so realistic, they look like they were plucked from the backyard and placed onto the prints.) In addition to the highly skilled reproductions of some of Mother Nature’s most colorful subjects, this is a great place to visit if you’ve got a beloved piece that’s a little worse for wear—as the gallery proclaims, its staff can perform corrective treatments on “anything on paper or canvas.”

312-642-5300, 10 E. Ohio St., Chicago, IL, 60611; audubonart.com

Best Virtual Exhibitions

• Neighborhood: Bronzeville
• Key Artists: Andre Guichard, Akin, Pearlie Taylor

You don’t even have to live in the Windy City to enjoy the offerings at Gallery Guichard (though it's certainly worth a visit)—co-owners Andre and Frances Guichard host virtual exhibitions that can be viewed any time day or night in a effort to fulfill the gallery's mission of bringing "multicultural artists specializing in African diaspora" to the people. Their offerings allow viewers can get to know the gallery’s copious global artists, check out collections via 3D photographs (the likes of which allow you to zoom in for a far more up-close-and-personal view of the pieces than you’d get in-person) and hear insider stories behind the works.

773-791-7003, 436 E. 47^th St., Chicago, IL; 60653; galleryguichard.com

Best Surrealist Art

• Neighborhood: Wicker Park
• Key Artists: Laura Lee Junge, Will Armstrong, Justin Miller, Irena Sarpenis

Jackson Junge largely revolves around co-owner Laura Lee Junge’s art, which is both surrealist, marked by abstract, free-flowing scenes, and expressionist in nature, but the 3,500 square-foot showroom is also home to several other contemporary artists. There’s Will Armstrong, for instance, who does his drawings with a series of pens and Chinese lettering quills, and Chicago artist Justin Miller, who explores “surreal interpretations of natural landscapes, wildlife, and architecture.” While larger pieces will cost you a pretty penny, the gallery sells its own artist-approved giclee prints in order to bring prices down for those with smaller budgets.  

773-227-7900, 1389 N. Milwaukee Ave., Chicago, IL 60622, j2gallery.com

Most Female-Centric

• Neighborhood: Pilsen
• Key Artists: Setsuko Aihara,  Carol Burin, Karin Fike

No topic is too taboo when it comes to artistic themes at this Pilsen gallery—particularly when it comes to the female experience. Featuring pieces that touch on everything from reproductive laws and sexuality to mental health, the exhibits are bold and powerful, just like the women and non-binary artists it represents from all over the world—key artist Aihara is from Japan while Burin and Fike hail from Chicago. Like Gallery Guichard, Woman Made also hosts virtual exhibitions, though you can also visit in person if you prefer to to opt for the full sensory experience.

312-738-0400, 2150 S. Canalport Ave. #4A-3, Chicago, IL, 60608; womanmade.org

Most Educational

• Neighborhood: Pilsen
• Key Artists: Frida Kahlo, Olga Costa, Ester Hernández

The National Museum of Mexican Art was founded in Chicago in 1982 to “stimulate knowledge and appreciation of Mexican art and culture.” It has since grown into its 48,000 square-foot space in Pilsen, where 69 artists across film, visual and performing mediums and 18,000 seminal pieces are currently on display to visitors. The museum also has rotating exhibitions: even Frida Kahlo’s works passed through its doors from April to August 2022. (Psst: It’s also free of charge except for events, like the upcoming “Bidi Bidi Boom Boom: The Selena Tribute Dance Party,” $30, May 11.)

312-738-1503, 1852 W. 19^th St., Chicago, IL, 60608; nationalmuseumofmexicanart.org

Best Street Art

• Neighborhood: Chinatown
• Key Artists: Sleepy Kitty Arts, Greg Gossel

With a specialization in street art and printmaking, this Logan Square transplant comes highly recommended by Jados, who loves its ultra-cool vibe that effectively captures Chicago’s graffiti art style into smaller prints, trinkets and more. With new material regularly making its way into the shop, there’s always plenty to see, even if you’ve visited before. Prices starting at $5 for a notecard, too, so finding something in your budget won’t be a problem: There’s even a payment system available for larger purchases.  

312-519-1972, 211 W. 23^rd St., 2^nd Floor, Chicago, IL, 60616; galerif.com