This small West Side museum takes self-taught artists seriously. The creators of the artworks displayed here might draw on knowledge gleaned from TV, pulp novels, ancient archaeology, country churches, or jails. These artists all come from outside the art world, and are forging their own visual vocabulary. That was especially true for Henry Darger, whose cramped studio has been recreated in the back of the gallery. His trademark blend of nostalgia, gore, horror, and camp consumed reams of paper and near every corner of his bleak apartment. Consider Intuit’s rotating exhibitions a monument to self-expression.

As you head out to Lake Shore Drive, you’ll drive past the Couch Tomb. Today, the stone mausoleum, built in 1858 for the hotelier Ira Couch, is the lone vault in green, grassy Lincoln Park. It wasn’t always this way: The tomb is the most visible reminder of the park’s past as a public cemetery. The vault is often described as being the oldest structure still standing in the path of the fire that tore through the city in 1871. Mysteries abound about why the structure stayed put, and just how many bodies are interred inside. You won’t solve them as you breeze by, but it’s worth a look.

Inside this stately museum—housed in a chateau inspired by Le Petit Trianon at Versailles—is a mix of hard science and compelling curios. There’s tons to see. Don’t miss the diorama of an operating theater, where a patient’s body would be on display to hundreds of onlookers, or the jumble of stones that once clustered in kidneys and other organs and now look more than a little like pieces of coral. Peruse the snake oil tonics on offer in a recreated apothecary, and gawk at the wacky ways people once used X-rays and ether as party tricks.

Some of Chicago’s most prolific and prominent architects and cultural figures were laid to rest in this rambling cemetery, and it’s got the dramatic (and odd) graves to prove it. Download a map from the cemetery’s website, or pick one up upon arrival to plot a course to the Ryerson Tomb, designed by Louis H. Sullivan and inspired by an Egyptian pyramid. Pay a visit to William Hulbert, too. He was part-owner of the Chicago White Stockings, which predated the Cubs, and, fittingly, his gravestone is in the shape of a baseball. When you return to the land of the living, make a pit stop at one of Andersonville’s many restaurants or cafes en route to your next stop.

Every inch of this shop is full of wonders, some more morbid than others. The offerings range from shells and insects to bloated things in jars, stuffed jackalopes, dental X-rays, bodybuilding pamphlets, and a papier-mâché King Kong. You could easily spend hours letting your eyes wander over the shelves and display cases, but don’t forget to take stock of everything dangling from the ceiling, too. You might need an extra carry-on bag to cart all of your finds back home.

Once you’ve stocked up on curios, it’s time to get on with the evening. First, head to the Green Door Tavern. The affable dive will probably be crammed with people chowing down on baskets of burgers and fries, but that’s not why you’re here. Walk right past them and down the staircase on your left. A cabinet full of tchotchkes is actually a door, and it opens into the Drifter, a tungsten-hued speakeasy. The sizable cocktail list comes printed on tarot cards, and the decor and eclectic performances, which run throughout the night, evoke carnival feats.  

Yes, the Chicago Loop is one the most-trafficked corners of the city, but it’s worth spending a couple hours here to take in some of its more rewarding spots. Start at the Chicago Cultural Center and dash in to glimpse the mammoth Tiffany Dome, then walk a couple blocks south to check out the storied Palmer House Hilton—named for the famed progenitor of the chocolate brownie and home to the Merz Apothecary, which has sold pharmacy goods since the late 1800s. Finally, walk down to the Berghoff for a quick strudel or schnitzel below stained glass and handsome wood details. When the founder, Herman Berghoff, opened up shop in the late 1800s, brews were five cents—and that included a sandwich, too. It was the first spot to earn a liquor license when Prohibition was repealed, and that prized document now hangs on the wall.

As you wind your way along Lake Shore Drive, stop off at this encyclopedic museum, which is south of the Loop’s main drag. The wide-ranging natural history collection opened in 1893, to coincide with the World's Columbian Exposition. It’s now on many tourists’ itineraries, but nooks and crannies still have the capacity to surprise. Dodge the crowds in the great hall and march straight down to the basement. The smell of melting plastic will lead you to the Mold-A-Rama machines, where a couple bucks buys you a T-Rex or apatosaurus souvenir with retro (and prehistoric) charm. Don’t miss the herd of narwhals suspended in an eternal dive next to pastel-colored picnic tables and vending machines, and be sure to check out the N. W. Harris Learning Collection, a lending library of 400 miniature dioramas full of taxidermied fauna and plastic flora that Chicago-area residents can borrow. Who doesn’t want a tiny fox to take home? The N. W. Harris facility is closed for some of the summer; check the website for details.

By the time the artist Theaster Gates snapped up this former bank for $1, in 2012, the once-elegant building had fallen ramshackle. A few million dollars later, it’s all freshened up, and serves as a community time capsule and an epicenter for art and activism. It houses rotating exhibitions and permanent collections—among them, books and magazines from Johnson Publishing Company, publisher of Ebony and Jet, an archive of 60,000 glass lantern slides from the nearby University of Chicago, and the vinyl collection of Frankie Knuckles, dubbed the “godfather” of house music. The building no longer accepts deposits, but traffics in plenty of cultural currency.

If you think you’ve pulled up at an elementary school or find yourself lost in an alley and wonder if your GPS has glitched, you’re probably just a few feet from Build Coffee. In addition to a mean latte and delicious sweets, the tucked-away cafe peddles zines, chapbooks, and comics, and has a lot of local news on hand—it shares a building with three journalism projects, including the in-the-know South Side Weekly.

This isn’t the first White Castle; it isn’t even the first one in the Windy City. But it is the one that locals rallied around when they thought the distinctive fortress-shaped building was threatened. Today, the turrets made with white-glazed subway tiles are protected under local landmarks law. You can no longer buy sliders here—it’s a chicken place now—but if you’re hankering, you can grab a bag at a newer White Castle right across the street.

Just kitty corner from both White Castles is Willie Dixon’s Blues Heaven Foundation. It houses records, performance gear, and more in the former stomping grounds of Chess Records, the label that once claimed such venerable acts as Etta James, Muddy Waters, Chuck Berry, and Bo Diddley. Drop in for a tour or to groove to concerts in the garden. Visit the website for an updated schedule.