These are the artsy essentials you can reasonably fit into a long weekend in the Windy City.
In Chicago, the very weather urges exploration of the city’s expansive artistic offerings. Each of my visits has been during the deepest part of its no-nonsense winters when the warmth of one of its many museums can be lifesaving in a literal sense. And I’m told that the sticky heat and humidity of peak summer is similarly indoor-inspiring—why not cool off with some of the world’s greatest artworks?
Climatic motivations aside, it is easy for art lovers of any predilections to spend countless days on end wandering the vast artistic opportunities afforded by the Windy City. To see it all during a short visit is impossible, so let’s go through a few essentials that you can and should fit into, say, a long weekend in Chicago.
No matter your tastes, the Art Institute of Chicago should be the most essential addition to your itinerary. Depending on your breadth of interest, it can easily demand three to five hours to give it its proper due. Masterpieces spanning all eras, traditions, and regions abound. Edward Hopper’s Nighthawks. Van Gogh’s The Bedroom. Seurat’s A Sunday on La Grande Jatte. A smattering of Jacob Lawrence. O’Keeffe, Rivera, Matisse, Hokusai, Warhol, Bacon, Pollack, and so on and so forth. Ancient Buddhist statues. American Gothic. You get the idea.
From there take the #3 bus for fifteen minutes to the Museum of Contemporary Art, which famously hosted the first American exhibition of Frida Kahlo. Here again, you’ll encounter some of the greatest works by renowned artists like Francis Bacon, Cindy Sherman, Jasper Johns, Jeff Koons, Chuck Close, Dan Flavin, Kara Walker, Rauschenberg, Warhol and the rest. The MCA also tends to have outstanding visiting exhibitions from the most exciting names working today. Currently on view is a major survey exhibition, “Nicole Eisenman: What Happened,” which showcases 100 works produced by the artist from 1992 to today.
Between these two museums, you have a full day of art. The former requires more time than the latter, so I’d suggest seeing the Institute in the morning, breaking for lunch, then hitting up the MCA. For a hearty bite on the way between the two, you can’t go wrong with Crushed By Giants Brewing Company.
From here I recommend three places that you can pick and choose based on your available time, location and inclinations. They’re a bit more niche, disparately scattered across the city, and in one case may still be closed for renovations.
The National Veterans Art Museum was initially launched with the involvement of soldiers who had participated in the Vietnam War, and today it displays works from thousands of veteran artists who engaged across a range of conflicts. Three exhibitions stand out. Inspired by the Tim O’Brien novel of the same name, The Things They Carried portrays the personal narratives of artists from the Vietnam War. On a related note, Above and Beyond—one of the largest memorials to American troops killed in Vietnam—is comprised of 58,307 dog tags bearing the names of the dead and serves as a chilling reminder of the human meat grinder that is war. And then there’s Vonnegut, which displays fifty prints by the famed novelist that tend to be of a more playfully surreal nature.
The National Museum of Mexican Art is an absolute eruption of color thanks to the south-of-the-border tendency to incorporate vibrant hues. Home to nearly 20,000 pieces dating from today on back to the pre-colonial era, here you’ll find one of the most impressive collections of Mexican indigenous art outside of Mexico itself, as well as a slew of stunning pieces from leading artists of the past century. Added bonus: it’s free every day.
If you’re visiting after the summer of 2024, check if Intuit: the Center for Intuitive and Outsider Art has reopened. Dedicated to gathering works from artists on the fringes of society, it’s a truly one-of-a-kind collection spanning outsider figures like Miles Carpenter, Minnie Evans, Mr. Imagination, Purvis Young, and Chicago’s own Wesley Willis and Henry Darger, among many others.
Speaking of Chicago’s own, spend some time simply wandering around and taking in the fantastic architecture. A perfect encapsulation of this is the Driehaus Museum, a restored late 19th-century house that is a compact masterpiece of art nouveau. The gilded ceiling in the Chicago Cultural Center is the largest Tiffany glass dome in the world. The Wrigley Building stands like a castle teleported straight out of the Renaissance. The biomimicry of Aqua Tower. The Blade Runner imperiousness of 875 N. Michigan Ave. The Dutch/Brutalist fusion of TheMART. The Robie House designed by Frank Lloyd Wright. The list could go on and on.
Finally, Chicago is well known for its fine comedic arts, so plan to hit up a comedy club some evening. The Second City is its most famed stage, but Zanies, the iO and Laugh Factory are all reliably funny options.
In terms of where to stay in Chicago, the city is packed with stellar accommodations, but if you’re leaning into art experiences book 21c Museum Hotel. It’s a quality hotel by all the usual metrics, but you’re there for the art, which is all over the place and frequently unusual. Also, get a hot dog. Few places in the world make such artistry of tubed meat.
