10 Bucket List Things to See and Do in Oak Park

Full of historical architecture, charming shops, and great dining, Oak Park is one of the crown jewels of Chicagoland.

Located in Cook County, about ten miles west of the Chicago Loop, Oak Park offers all of the charms of a small town with the convenience and accessibility of city living. This community is contemporary and classic, all at once — making it a great place to call home or to explore for a few days.

What should be on your “bucket list” of things to see and experience in Oak Park? Here are ten ideas to add to your list:  

1.) Experience Live Theater in the Great Outdoors

There’s nothing like seeing a talented troupe of actors, directors, and designers breathe new life into a classic play — especially when you’re seeing their work take shape in one of the most beautiful outdoor venues around. Oak Park Festival Theatre is the midwest’s oldest professional classical outdoor theater. This talented company has been entertaining families at Oak Park’s idyllic Austin Gardens since 1976, and it’s well worth seeing these performers in action if you get the chance. To round out the experience, why not bring a picnic to enjoy before the show, courtesy of a local Oak Park market?

For more information or to plan your visit, be sure to read on at Festival Theatre’s official website, available here.

2.) Explore the Works of Frank Lloyd Wright

One of the preeminent modernist architects in American history, Frank Lloyd Wright’s incredible creations can be spotted all over the midwest. But you’d be hard-pressed to find more of his stunning designs in one convenient location than you will in Oak Park. Wright designed dozens of homes and structures which are still standing throughout Oak Park, including the striking Unity Temple, which many consider his masterpiece. Wright also called Oak Park his home, and architecture aficionados can tour his one-time house and studio today.

For more on Frank Lloyd Wright’s contributions to Oak Park, or to schedule a tour to see this master’s work up close, the Frank Lloyd Wright trust has more information, available here.

3.) Discover Where Writer Ernest Hemingway Grew Up

Before he became legendary for writing works like The Sun Also Rises and The Old Man and the Sea, Ernest Hemingway was just a boy growing up in Oak Park. To learn more about how this American icon got his start, you can pay a visit to his childhood home, a fabulously restored Queen Anne house originally built in 1890. Tours of the home, now officially known as the Ernest Hemingway Birthplace Museum, are available for individuals and groups on a regular basis. The Ernest Hemingway Foundation of Oak Park also hosts many community events and celebrations at the museum.

To learn more about Hemingway or start planning your trip, you can visit the official website for the Ernest Hemingway Birthplace Museum here.

4.) Catch a New Release in a Vintage Movie House

What would make seeing the latest Spider-Man movie even better? How about seeing it come to life in one of the most incredible art deco movie houses in all of Illinois? Oak Park is home to the famous Lake Theatre. Originally built in 1911 under the direction of renowned architect Thomas Lamb, the Lake has been through many changes over the years. Today, the venue is operated by Classic Cinemas, which has helped restore this classic picture palace to its former glory — while also bringing in modern amenities, such as state-of-the-art sound systems and ultra-comfortable seating.

To see showtimes and discover more about the history of this Oak Park gem, you can visit the Lake Theatre’s official site, here.

5.) Marvel at the Greenery at the Oak Park Conservatory

Billing itself as a “hidden oasis” in the heart of the community, the Oak Park Conservatory offers visitors the incredible opportunity to experience plantlife from a variety of ecosystems, including the Mediterranean, the tropics, and the desert. There’s also plenty of flora and fauna from the midwest on display in the gardens around the Conservatory, in case you wanted a little taste of home, as well. In addition to welcoming more than 40,000 visitors a year, the Conservatory also hosts special events throughout the year, including a spring plant sale.

To learn more or plan your visit, please visit the Oak Park Conservatory’s official website, available here.

6.) Let Your Little Ones Play and Learn at Wonder Works Children’s Museum

The Wonder Works Children’s Museum is rooted in the simple idea that creativity and play are vital tools for helping kids grow and thrive. And this impressive museum gives young children plenty of chances to explore. The museum includes “experience zones” that encourage kids and parents to get moving and try out different activities, from farming, to puppetry, to making their very own TV show.

Want to discover more about Wonder Works? You can read more about this unique destination for families here.

7.) Find Your New Favorite Decorations at an Oak Park Boutique

Whether you want to change up your decor for the holidays, find the perfect gift for friends and family, or gather the supplies to make your very own home goods, you can find what you’re looking for at one of downtown Oak Park’s eclectic, independent shops. For instance, whether you’re looking for accessories or cookware, CarefulPeach Boutique has a wide array of chic, unique products worth checking out. For home goods and gift items lovingly crafted and ethically sourced from artisans around the world, Ten Thousand Villages is a must-see. And then there’s Taylor’s Gifts and Bonsai, home to handmade decor and design pieces carefully chosen to enrich any living environment.

8.) Rekindle Your Love for Art on Harrison Street

Also known as Oak Park’s Art District, Harrison Street is home to plenty of local galleries and studios with offerings sure to pique your interest — and maybe even introduce you to your next favorite artist. Black Moon Gallery & Studio, for instance, is home to a collective of artists, and routinely displays new work from photographers, painters, and more in its lovely gallery space. Nearby, Gallery PINK hosts the latest and greatest in fine art, while Expressions Graphics produces and displays stunning printworks from artists in the community.

9.) Expand Your Horizons at an Oak Park Bookstore

Book worms, rejoice! As the home of such luminaries as Hemingway and Frank Lloyd Wright, it should come as no surprise that Oak Park is a community that celebrates reading. If you’re looking to expand your literary collection or rediscover a favorite novel from your past, it may be time to stop in one of Oak Park’s amazing independent bookstores. Book lovers have plenty of great spots to choose from, including The Book Table, Centuries & Sleuths, and The Looking Glass Books.

10.) Savor the Flavors of Oak Park’s Brewing and Winemaking Community

Ready to taste something new? In recent years, Oak Park’s craft beer and wine scene has really started to flourish. Today, thirsty visitors to Oak Park have a number of excellent options to consider. For the wine drinkers looking to experience something fresh, there’s Cooper’s Hawk Winery & Restaurant, which serves up delicious modern cuisine alongside glasses of Cooper’s Hawk signature wines. If beer is more your style, Oak Park has craft brews sure to satisfy, served up in throwback brewpubs, like the Oak Park Brewing Company, and cutting edge taprooms, like the one you’ll find at Kinslahger Brewing Company.

Want to keep exploring Oak Park? Be sure to check out our guide to this historic community’s housing market, available here. Want to get in touch with a Baird & Warner agent in Oak Park? You can find more information on our Oak Park/River Forest office here.