Chicago: A Weekend Guide for the Curious Traveler - Atlas Obscura

Weekend Guides for the Curious Traveler

Just when you thought you knew the Windy City, it finds new ways to surprise you.

Day 1
Art and Identities

A continually intriguing metropolis, from past to present.

Unusual Museum

1. Intuit: The Center for Intuitive and Outsider Art

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.

756 N Milwaukee Ave, Chicago, IL 60642

The Couch Tomb is now the only mausoleum in Lincoln Park. Walt Flood
Leftover Grave

2. Couch Tomb

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.

Off W LaSalle Dr in Lincoln Park, Chicago, IL 60614

Prosthetic eyeballs and scores of other tools are on view at the International Museum of Surgical Science. Gina Kelly/ Alamy
Medical Oddities

3. International Museum of Surgical Science

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.

1524 N Lake Shore Dr, Chicago, IL 60610

Graceland Cemetery is speckled with works of art, including Lorado Taft's somber bronze monument, Eternal Silence, from 1909. IvoShandor/CC BY-SA 3.0
Historic Graveyard

4. Graceland Cemetery

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.

4001 N Clark St, Chicago, IL 60613

Oddities abound at Woolly Mammoth. Jessica Leigh Hester
Curio Shop

5. Woolly Mammoth Antiques and Oddities

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.

1513 W Foster Ave, Chicago, IL 60640

Hidden Speakeasy

6. The Drifter

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.  

676-8 N Orleans St, Chicago, IL 60654

Day 2
The Loop and South Side

Familiar streets worth rediscovering.

Like many Chicago stalwarts, the Berghoff has World's Fair roots. Michael Brown
Cultural Walk

1. The Unseen Loop

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.

78 E Washington St, Chicago, IL 60602

At the N. W. Harris Learning Collection, dioramas can go home with you. Jessica Leigh Hester
Dioramas To-Go

2. The Field Museum

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.

1400 S Lake Shore Dr, Chicago, IL 60605

The Stony Island Arts Bank houses Johnson Collection, a trove of books and magazines. Courtesy of the Rebuild Foundation/Stony Island Arts Bank
Activist Art

3. Stony Island Arts Bank

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.

6760 S Stony Island Ave, Chicago, IL 60649

Thanks to its newsy neighbors, Build Coffee is a great place to read. Alex Jung for Build Coffee
Perfect Pitstop

4. Build Coffee

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.

6100 S Blackstone Ave, Chicago, IL 60637

Fast-Food Landmark

5. White Castle #16

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.

43 E Cermak Rd, Chicago, IL 60616

Blues Heaven’s outdoor space fills up during summer concerts. Eric Allix Rogers
Musical Archive

6. Blues Heaven

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.

2120 Michigan Avenue, Chicago, IL 60616

Where to Stay
Chicago Athletic Association

Formerly a retreat for the moneyed (and male), this circa-1890s building is now open to everyone. The rooms feature luxurious, modern details, but the hotel is hardly short on historic charm. The tiled pool, long-since drained, is an events space. Fireplaces flank the drawing room, which is stuffed with leather and wood, and bocce and other games get rolling next door.

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2 Perfect Days in Pensacola

If you thought Pensacola, Florida—with its powder-white sand beaches, near-perfect weather, and fresh seafood—was just a place to soak up the sun, think again. In fact, the city and beach of the same name is the site of the first European settlement in the continental United States. Established by Spanish explorer Tristán de Luna in 1559, it was christened Panzacola, a name of Native American origin and the precursor to the city’s modern name. The destination is also the birthplace of U.S. naval aviation and is still home to a naval air station and the thousands of service members stationed there, as well as the Blue Angels, the flight squadron famous for their death-defying fighter plane stunts. This delightful coastal city is an ideal, if somewhat quirky, blend of historical sites (on land and underwater) and activities to get your adrenaline flowing.


Taste of Tucson

The people of Tucson have been eating off the land for 4,100 years. From grains to livestock to produce introduced by missionaries in the 1600s, this UNESCO City of Gastronomy is home to some of the oldest farmland in North America. What once was old is new again in The Old Pueblo where ancient flavors are found in nearly every dish — trendy to traditional.


North Iceland’s Untamed Coast

Any travel enthusiast would be hard-pressed to open any social media channel and not see photos of Iceland, with its jaw-dropping peaks, natural hot springs, pure glaciers, northern lights and snow-covered landscapes. But the island nation’s appeal goes well beyond the well-worn paths of Reykjavik, the Golden Circle and the southern region's countryside. Travel to the untamed north along the Arctic Coast Way to discover otherworldly beauty—sans crowds—around every bend.

Look closely and wander widely: Parliament Square is full of charm.

Hidden Edinburgh

Crowds clog Edinburgh's Royal Mile, the main artery between Edinburgh Castle and Holyrood Palace. The road is dotted with stores selling Nessie trinkets and lined with bagpipers and street performers pulling off dazzling tricks. But look beyond the tartan tourist traps, and you’ll discover tucked-away gardens, remnants of the city’s medieval past, and much more.


Hidden Haight-Ashbury

In 1967, 100,000 artists, activists, and hippies gathered in San Francisco’s Haight-Ashbury neighborhood for the Summer of Love. Janis Joplin and Jimi Hendrix played free concerts for fields of college dropouts, and San Francisco established itself as a countercultural capital. More than 50 years later, in a city increasingly known for Twitter and tech rather than art and activism, travelers who come on a pilgrimage are often disappointed to find expensive, skin-deep psychedelia. But if you know where to look, you’ll find a walk down Haight Street to be wonderfully weird, full of historic links to hippiedom and modern takes on the vibe.


The Many Flavors of NYC’s Five Boroughs

More than eight million diverse individuals call New York City home, and many of them share their heritage through food. Whether it’s a billiards hall that serves stellar Bhutanese fare or a mosque where Malian vendors sell snacks for just a few hours each Friday, the city offers a vast culinary landscape for those willing to explore it. Venture beyond the flashy hotspots with months-long waiting lists and you’ll find New York’s true flavor lies within the small restaurants and stands rooted in its thriving immigrant communities.

Musical instruments in the courtyard of SecondLine Arts and Antiques in New Orleans' French Quarter.

Hidden French Quarter

It may be famous for Mardi Gras, but New Orleans has subtle, surprising wonders on tap all year long—even in the touristy French Quarter. Around every cobblestoned corner, you’ll find historic ephemera, bits of Creole culture, environmentalism, and no shortage of spooky stories, whenever you happen to visit.


The Metropolitan Museum of Art

From the street, the Metropolitan Museum of Art is hard to miss: The institution’s two-million-square-foot main building, at 1000 Fifth Avenue, spans four New York City blocks and stretches into Central Park. Inside the galleries, you’ll find thousands of objects spanning 5,000 years of world history. With so many treasures under one roof, it's inevitable that some fascinating pieces are tucked into the museum's lonelier nooks and crannies, hiding in plain sight. The next time you spend a day at the museum, keep an eye out for these overlooked wonders.

The RV/MH Hall of Fame.

Motown to Music City Road Trip

Detroit and Nashville are synonymous with two all-American music genres. It’s no surprise that visitors flock to these cities each year to get a feel for the places where artists such as Marvin Gaye, Diana Ross & the Supremes, Johnny Cash, and Dolly Parton began their careers. A (relatively) straight, north to south route connects the two cities, as does musical heritage. Load up the RV, make sure your speaker system is in tip-top shape, and create a playlist filled with old-school Motown and Country hits. If you're not driving on the trip down south, you should be dancing.

The East Texas Bayou.

Gulf Coast Road Trip

The terrain along the Gulf of Mexico is sometimes called the “Third Coast,” but for an offbeat road trip, it’s second to none. Starting in Houston and ending in Pensacola Bay, this journey takes you through some of America’s most diverse landscapes. You’ll cross Cajun swamps, drive along sparkling white sand beaches, and even spend some time in the Big Easy. Take an RV and camp along the way to truly immerse yourself in this wondrous region. The world’s largest gulf, it turns out, holds some of America’s best-kept secrets.

Coachella Valley Preserve.

Hidden Coachella Valley

The Coachella Valley and its environs boom in the spring, when tens of thousands of music lovers flock to catch their favorite artists perform in front of a dramatic, mountainous backdrop. But this region stays wonderfully weird all year long. If the festival drew you to the area and you only have a day to explore, choose a direction: Either head north, toward Joshua Tree and Landers, or southeast to the Salton Sea and nearby oases for a blissful respite. If you can spare a couple of days, lucky you—go forth and see it all.

A view of L.A. from the top of Highland Park.

Highland Park

Los Angeles’ Highland Park is a diverse, eclectic neighborhood that Native Americans and Latinx communities have inhabited for centuries. Celebrated for its history, art scene, ethnic diversity, and cuisine, Highland Park is filled with surprising delights that more and more people are discovering every day. Exploring the neighborhood's nooks and crannies is one of the most rewarding ways to spend a day in L.A.

The heart of Venice.


Once referred to as “The Coney Island of the Pacific,” L.A.’s beachfront neighborhood of Venice has long been a popular tourist destination. Its colorful characters, quirky architecture, and carnivalesque atmosphere are well-known the world over. But take a moment to look past the kitsch, and you’ll discover a place where artistic ingenuity thrives more than a century after Abbot Kinney endeavored to bring a grandiose version of Venice to America. The bohemian beehive has always attracted artists and performers, and everyone is welcome to enjoy the show.

Artist Colette Miller's tribute to the City of Angels.

L.A.’s Downtown Arts District

The 1970s brought a wave of artists into this former industrial area in Downtown Los Angeles. They sparked a fuse of creative imagination that burned for years. Up-and-coming creators took advantage of the then-low rents and built a foundation for the creative mecca that exists here today. In its infancy, L.A.’s Downtown Arts District came to life behind-the-scenes, with artists mostly working in closed studios. Today, the art has spilled onto the streets in the form of colorful murals, attractive gallery spaces, and stylish storefronts. But the curious explorer can still find literal and figurative traces of the ‘70s. In addition to the more historic spots that remain, a creative, entrepreneurial spirit abounds.

The Whitehall Banqueting House is full of topsy-turvy views.

Hidden Trafalgar Square

Wedged between Charing Cross and Leicester Square, Trafalgar Square is known for the throngs of people flocking to its famous attractions. Weave around the tourists on the National Gallery stairs and dodge the crowds clogging the street corners. Instead, duck down dreamy alleys and pop into unique, overlooked museums and shops. There, a secret side of this busy area waits to reveal itself.

An elevator shaft in Tribeca opens to reveal a museum of small wonders.

Secrets of NYC’s Five Boroughs

Few cities on Earth are as well-trodden as New York–but as any intrepid traveler knows, the more you explore a place, the more wonders you find. You may not be able to discover all of these spots in a single trip, but that could be a good thing. No matter how many times you return, the city that never sleeps never ceases to surprise. Visit NYCGo to uncover more of the city’s secret spots.

Plenty of sweet treats are on offer at Pastelería Ideal

Mexico City's Centro Histórico

Anchored by the Zócalo plaza and the architectural splendor of the Palacio de Bellas Artes, Mexico City's historic center rightfully draws scores of visitors from around the world. If you look, smell, and taste carefully, you’ll also find a universe of culinary offerings that tells stories of immigration, adaptation, and imagination. With the help of Culinary Backstreets, we assembled a primer on eating and drinking your way through the district.

View of the Hollywood Sign from Babylon Court

Hidden Hollywood

Hollywood Boulevard is world-famous—for the Oscars and the Walk of Fame, for schlocky souvenir shops and crowded tour buses. But beyond the terrazzo stars and the occasional celebrity sighting, there’s plenty left to discover. Here’s how to make Hollywood’s acquaintance, whether you’re a visitor or a local who keeps a practiced distance from these busy, saturated blocks. Look closer and you'll find a neighborhood full of nature, history, and wonder.

A subway entrance in Times Square.

Hidden Times Square

There's the Times Square you know, full of blazing billboards, selfie sticks, and costumed characters. Then there's the less familiar one, beyond the lights—the nooks and crannies that most visitors to Midtown Manhattan overlook. They're not obvious, but surprises can still be found along this world-famous stretch of real estate.

Upper Hoh Road, Olympic National Park, Oregon.

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The dome of Estrela Basilica in Lisbon.


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New York City's most diverse borough is also its most rewarding.


San Diego

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Find surprises around every corner in a U.S. city that embraces history like no other.