With more than 200 venues, nationally acclaimed productions and an annual Theatre Week, Chicago, Illinois, boasts one of the most lively performing arts scenes in the United States. And while the city’s most frequented theaters are located in their very own district within the Loop, the Second City has no shortage of venues to visit across its many neighborhoods.
Magnificent Mile: Broadway and Beyond
In the Magnificent Mile neighborhood, you’ll find some of the city’s best luxury retail boutiques, fine dining and can’t-miss sights. The 154-foot (47-m) limestone Water Tower — one of the only buildings to have survived the Great Chicago Fire of 1871 — now houses the Lookingglass Theatre.
This Tony Award-winning company focuses on original shows and contemporary adaptations of classic stories, from Alice in Wonderland and Moby Dick, to Treasure Island and Arabian Nights. Each ensemble undergoes improvisational training in everything from dance to the circus arts to ensure no two productions are alike.
Only steps away is the Broadway Playhouse, a 550-seat auditorium tucked inside of the neighborhood’s Water Tower Place shopping center. It offers pre-Broadway and off-Broadway productions along with magic shows and comedy acts.
Before showtime head to dinner at Spiaggia, a neighborhood mainstay for upscale Italian fare (and a personal favorite of the Obamas). Take in Mag Mile views between regionally inspired courses like spaghetti with uni and black garlic, or lamb loin with fava pesto and morel mushrooms. Do opt for the wine pairings from beverage director Rachael Lowe, whose list is as approachable as it is versatile.
After the show, head across the street for a nightcap at NoMI, where just a handful of coveted seats alongside the 8th-floor windows give guests unparalleled views of the Water Tower and Michigan Avenue. If it’s a sweet fix you’re after, swing by Ghirardelli, where over-the-top sundaes are the specialty.
Hyde Park: Theater on Campus
For a venue with an even richer history, head south to Hyde Park and Court Theatre, which opened its doors in 1955 on the campus of the University of Chicago. Its location informs the company’s theatrical goals in reviving lost masterpieces, discovering modern classics and exploring the African-American theatrical canon.
Bonus: If you’re coming from the North Side, enjoy stunning views of Lake Michigan along the way.
Arrive to the neighborhood early for a pre-theater dinner at The Promontory, a buzzing restaurant, bar and concert venue. Centered around a brick hearth, this eatery is all about classed-up comfort fare, from bacon-date tartines and grilled oysters, to farm chicken with Parisian gnocchi and roasted carrots.
Lincoln Park: American Playwrights in Focus
Like Court Theatre, the acclaimed Steppenwolf Theatre shares a neighborhood with a university, in this case DePaul, which has inspired the company to offer diverse programming that appeals to multi-generational audiences.
Founded in 1974 by actors Gary Sinise, Terry Kinney and Jeff Perry, Steppenwolf features a multi-genre performance “LookOut Series,” in addition to its seven-play regular season and young adult programming.
Do as the locals do with a pre- or post-show reservation down the street at Boka, a neighborhood favorite that isn’t short on accolades — including six consecutive Michelin Stars.
Credit that staying power to chef Lee Wolen’s seasonal modern American menus, comprising plates like grilled bass with black olives and green garlic, and charcoal grilled beets with pumpkin seeds and licorice. Be sure to stick around for dessert; pastries from Meg Galus are as fun to look at as they are to eat.