Design Destination: Oak Park, IL
A 24-hour guide to the artsy, under-the-radar design mecca
I’ve posted Notes with my travel photos from Strasbourg, Madrid, and London, so you might be surprised that my first travel piece is on an midwestern American suburb. If you’ve heard of Oak Park, it’s likely because Frank Lloyd Wright lived and worked here and Ernest Hemingway was born here.
If you haven’t, rest assured that it’s a great, low-key art and design destination, and I’m not just foisting my hometown at you. Travel Lemming recently named it one of their 50 Best Places to Visit in 2025. Oak Park is the kind of town American tourists are thrilled to find while abroad: walkable, with leafy streets packed with historic architecture, indie boutiques, and great food. It’s also one of the few American cities designated as an arboretum. It’s absolutely worth a daytrip if you’re visiting Chicago - or if you live in the city and haven’t been yet.
Notably, design fans usually visit Oak Park because it has the biggest collection of Frank Lloyd Wright buildings in the world. In addition to his lauded home and studio, he designed 25+ local landmarks, including Unity Temple. Beyond architecture, Oak Parkers are incredibly proud of their town’s diversity and creativity.
Betty White was born here, Cecily Strong grew up here. It’s the launching point for fashion icon Tavi Gevinson and her generation-defining magazine Rookie. Ludacris attended freshman year at the local high school, the indie band The Fiery Furnaces went there too. Peter Sagal of Wait! Wait! Don’t Tell Me kept a quarantine diary of his lockdown life here. All of these creatives —and the list goes on — have been influenced by the artistic undercurrent of life in Oak Park. There’s a near constant stream of local art shows, live music, street festivals, charity housewalks, and more.
WALKING GUIDE
Oak Park is relatively large, spanning several miles and both sides of the Eisenhower Expressway. This guide purposefully skips a few neighborhoods in favor of walkability. You can take the green line or Metra and walk to everything I’ve included. If you take the Green Line to the Oak Park stop, you’ll start in the Hemingway District. (Just a note: take the Green Line at peak travel hours, rather than late at night). If you take the Metra, you’ll begin on Marion Street.
Of course, it being the Midwest, you can also drive and park easily. If you do arrive by car, I have some honorable mentions listed at the bottom that are worth driving to, including well-known local favorites in Elmwood Park, Berwyn, and Forest Park.
Hemingway District
SEE
Cheney Mansion & surrounding homes: This 12,000 sqft mansion was designed and built by Charles E. White, an apprentice of Frank Lloyd Wright. You don’t need to tour it, but it’s a pretty landmark and the streets surrounding it include a 1920s Storybook mansion and several Prairie-style homes.
Ernest Hemingway Birthplace & Museum: This Victorian home was the childhood residence of Ernest Hemingway. Worth a stroll to peek at, even if you bypass it for a tour.
En Route between here & Marion Street District: While you walk, you’ll pass Scoville Park and the Oak Park Public Library, which won an award for best new construction by the Chicago Building Congress Merit Award after its completion. It features a green roof, and almost the entire east side is angular windows that face the park. You’ll also pass the post office, designed by Charles E. White, and several churches, including Grace Episcopal Church, considered one of the best examples of Gothic Revival architecture in America.
EAT
Spilt Milk: A bakery tucked away on South ave, directly off the Oak Park Green line stop. It’s an excellent place for a morning coffee to kick off your tour. Their buttermilk biscuits are amazing. They also carry a wine, Torres potato chips, and a few small home decor items.
Grape Leaves: A delicious, small BYOB Moroccan restaurant, owned and run by Moroccan chef Karim Benyaich. His childhood in Rabat — in a palatial home with 14 family members and endless guests — influenced both his hospitality and menu.
Amerikas: A nuevo Latino restaurant that’s especially great for brunch. Beautiful presentation — I once had a dessert served in a coconut covered in flowers — and really good fusion food.
Dessert at Amerika’s
SHOP
Gem Jewelry and Home: Owner and jewelry designer Laura Kitsas opened Gem 20 years ago to sell her own handmade pieces, and has since expanded to include other chic jewelry brands, as well as home decor. Her signature simple drop necklaces and earrings are consistent bestsellers.
Gepetto’s Toy Box: Their motto is “toys with the magic still in them” and the store itself is pretty magical as a result. Their focus is on quality, long-lasting toys, crafts, games, and costumes, mostly from small or European brands like Haba, Djeco, and Peaceable Kingdom.
Olive & Well: An olive oil boutique, focused on small batch groves throughout the world. In addition to carrying dozens of types of olive oil, Olive & Well also sells aged balsamic vinegars and food products.
Manouche: A tiny boutique, run entirely by owner Kim Shimkus. Her curation focuses on sustainable, artful pieces more than trends: think well-traveled & effortlessly put together. Brands include Munthe, Le Mont St Michel, and The Great.
Marion Street, via Compass Real Estate
Downtown Oak Park & the Pleasant District
SEE
Unity Temple: After the original Unity Temple burned to the ground in 1905, the church commissioned Frank Lloyd Wright to build a new one. The result is considered a masterpiece of Prairie-style architecture and one of Wright’s most outstanding public buildings.
Pleasant Home: A 30-room mansion designed by architect George W. Maher in 1897. Pleasant Home is considered one of the first and best examples of Prairie style homes. Through their website, you can book a one-day tour of three sites: this, the Cheney Mansion, and the Oak Park Conservatory.
Mini Murals: Look at the embankments alongside the train tracks, and you’ll see a community mural project, launched by the village in 2010. It’s an ongoing public art project, and each original painted was done by a local artist.
A wall mural in the tasting room of Anfora Wine Merchants
EAT
Blackout Baking: Delicious cookies, brilliantly sized so that you can try several. Their black, streamlined cookie boxes make excellent hostess gifts or presents to bring home from your trip.
Anfora Wine Merchants: A chic enoteca with an excellent selection of Italian wine. They also have a small menu, with delicious foccacia bread. In the summer, you can enjoy on a glass of wine outside & people watch on Marion St, and there’s a small tasting room in back for less pleasant weather.
Ciro: Not headed to Capri this year? No worries - eat here. Chef Ciro Parlato cooks regional food from his home island in a teeny restaurant. It’s BYOB, so locals stop by Anfora for wine first.
Hecho En Oak Park: There’s no bad Mexican food in Oak Park - Maya Del Sol and Hoja Santo are also great. However, Hecho is my favorite for street tacos and strong margaritas, and well-situated for a lunch stop. (Note: If you’re in Chicago on vacation, don’t leave without eating Mexican food - you haven’t really been here if you don’t. I would prioritize it over deep dish pizza, hands down.)
Crepas Culichi: A French & Mexican fusion restaurant, unabashedly geared toward Instagram. The presentation of their drinks are the main attractions, and thrilling to children. The milkshakes are covered in sprinkles and marshmallows, while the pink lemonade comes with an enormous pink bunny ice cube.
Baskets at The Careful Peach, via their website
SHOP
Careful Peach: Artist and unabashed Francophile Karen Morava stocks “the Peach” with French wine and pantry staples, bath and body products from Panier de Sens, Caudalie, Rue de Marli and more, and beautiful home decor, including tableware from Jurlique, sterling silver picture frames, colorful candles, and wicker baskets. By far one of the most popular stores in the area.
Pumpkin Moon: An Oak Park staple that just celebrated 30 years in business. Not a design destination, but an old-fashioned novelty store, with everything from pranks and anime merch to fortune fish and Pop Rocks. It’s impossible to leave without buying something random and delightful.
Fitzgeralds Fine Stationary: Skip the Paper Source around the corner and shop here. Owner Colleen Fitzgerald carries stationary for every occasion, as well as home products from Thyme and Rifle Paper Company.
Sugarcup Trading: Adorable kids boutique, with clothes from brands like Tea and Mayoral, guitars from Loog, toys from Maileg , a well-curated selection of books, and more.
Crafters & Weavers/ The Gold Hatpin: This is two stores, but in one space. Crafters & Weavers is known for their Shaker and Mission-style furniture. However, I’m recommending it for the collection of Persian and Moroccan rugs in the back. I’ve bought two rugs here, and they’re both beautiful. The Gold Hatpin, tucked charmingly in its own space in the back, sells wonderful estate and vintage jewelry sourced by jeweler Diane Richardson.
The Playroom at the FLW Home and Studio,. Photo by James Caulfield via The Frank Lloyd Wright Trust
FRANK LLOYD WRIGHT DISTRICT
SEE
Frank Lloyd Wright Home & Studio: If you only go to one tourist site, it should be this one. Wright’s home and studio is a precursor to the Prairie style he developed, and a fascinating look at his artistic evolution. There are daily tours of the home itself, as well as the popular Wright Plus Walking Tour in May, which takes you through the Frank Lloyd Wright historic district. It sells out every year, so best to plan ahead.
Kenilworth Ave & Forest St (the streets around the FLW Studio): Absolutely gorgeous homes, from Queen Annes to Gothic Revival to Prairie style. One of the houses on Kenilworth was carted wholesale from south Oak Park because of a dispute between neighbors.
EAT
Broken Tart: Yes, another bakery. I’m not even a huge sweets person, but I’d be remiss not to mention local standout Broken Tart, located a few blocks west of the Frank Lloyd Wright Home. Everything here is delicious, but the olive oil cake in particular has a devoted cult following.
SHOP
MOOD the Shoppe: A boutique home store, owned by local interior designer and builder Candy Scott. Modern art, furnishings, and decor, with a focus on muted tones and natural materials.
IF YOU DROVE
Oak Park Arts District: A bit further afield from downtown, which is why I didn’t include it in the walking section. The shops here include galleries like Purple Sun Arts and Fifty First Street and craft stores like Dye Hard Yarns and Bead in Hand. There’s also a few great restaurants, including Mora for sushi and the Oak Park outpost of Publican Quality Bread. The Happy Apple Pie Shop is another local favorite.
Johnnie’s Beef (Elmwood Park): The absolute best Italian beef place. Order a juicy beef and an Italian lemonade, and bring cash to pay. It’s been an iconic local spot for 60+ years, but gained even more fame after it was featured on The Bear.
Fitzgeralds Nightclub: (Berwyn) Fitzgeralds was recently listed on The National Register of Historic Spaces. It’s a fantastic music venue, as is the Sidebar next door. Just see whoever is playing the night you’re there. It’s skews neither young nor hip, but the crowd is mostly devoted music fans and local musicians. Standout events include the annual performance of The Band’s Last Waltz album, by local band The Zimmerman (it sells out every year), the multi-day American Music Festival in July, and their popular Charlie Brown Jazz brunches during the holidays.
New Rebozo: If you love mole sauce, or if you’ve never eaten mole, go here. Chef Paco is renowned for his 20+ varieties of mole — and for his charming tableside descriptions of the day’s specials. The mole enchilada sampler is insanely good. Once, while home from London, I drank too many margaritas and begged him tearfully to open a London location. Not my proudest moment, but I stand by the sentiment.
If you do visit, please let me know what you think and where you visited! Truly, Oak Park is a gem and an undercover spot to visit in an overcrowded tourist market.