This Artsy Chicago Suburb Is Home To America's Oldest Music Festival And A Lively Downtown Full Of Events

Tucked away in Chicago's North Shore suburbs, Highland Park is one of Illinois' best under-the-radar gems. With its vibrant downtown and rich array of festivities, Highland Park is the perfect addition to a Chicago trip. As an arts and culture hub, it's also home to a number of exciting events — namely the Ravinia Festival, which is considered one of the country's oldest outdoor music festivals. Featuring more than 100 summertime offerings that showcase genres ranging from classical to pop, jazz, R&B, indie, rock, and country, Ravinia is a Highland Park cornerstone.

Running from June until the last day of August, the festival has become a local tradition since it premiered in 1904. Throughout its storied history, Ravinia has been the world's summer opera capital (from 1919 to 1931) and hosted the Chicago Symphony Orchestra's very first summer residency (in 1936). Over the years, music legends like Louis Armstrong, Elvis Costello, Diana Ross, Stevie Nicks, Lady Gaga, and many more have graced Ravinia's stages.

Now run as a nonprofit, Ravinia focuses on making music accessible by supporting numerous educational initiatives like building orchestra programs in elementary schools. Want to catch the lineup for the current season? Find it and purchase tickets on Ravinia's official website.

Apart from Ravinia, you'll find plenty of spirited events in Highland Park, particularly in its walkable downtown, where Food Truck Thursdays and regular farmers markets take place. To sample some of the city's best culinary delights, don't miss Taste of Highland Park. Held for two nights in June, it features local vendors alongside music and theater performances. August's Port Clinton Art Festival has become another neighborhood gem over the past 40+ years and highlights more than 200 of America's best artists alongside vendors and lots of family-friendly entertainment. In October, experience Stews & Brews, a cozy event pairing cold-weather comfort dishes like pozole, goulash, and more with craft beers and delicious warm drinks like spiced ciders.

With about 450 businesses throughout downtown's Central Business District, Highland Park also has plenty to offer when it comes to shopping and dining. For one-of-a-kind fashions, head to My Sister's Circus, which has made Highland Park its home for the past 25 years. For all sorts of antique items and collectibles, check out Vintage Rescue. Highland Park's food scene is also diverse, with cuisines ranging from Mexican (the well-rated La Taquiza is an excellent choice) to Eastern European (don't miss one of the neighborhood's top spots, Cafe Dacha, which serves dishes like blintzes and stuffed cabbage).

Thanks to community events and organizations, artistry is at the core of Highland Park. One of the leading theater companies in North Shore, Highland Park Players hosts a number of performances each year. Meanwhile, Highland Park Strings performs four annual concerts, all free of charge. Creatives can also enjoy The Art Center Highland Park, a beloved local space home to numerous exhibits, fun events like recycled art sales, and hundreds of classes and workshops.

Just 30 minutes away from Chicago O'Hare International Airport by car (if you have an hour and 40 minutes to spare, you can opt for public transportation), Highland Park is a must-visit stop with activities that rank among the best things to do in Chicago. Hotel options in the area are limited, but Courtyard Chicago Highland Park/Northbrook is a great local choice, offering features like an on-site restaurant, a fitness center, and an indoor pool. Surrounding Highland Park, you'll also find plenty of other choices, such as Deer Path Inn, a highly-rated and luxurious accommodation. Located just 15 minutes away in Lake Forest (where you'll find Illinois' breezy clearwater beach), the four-star hotel has been around since 1929 and offers multiple award-winning dining options, a 24-hour fitness room, and plenty of historic charm.