You Don't Know Chicago Until You Try These

If you think you know Chicago, take a look at our unique alternatives to the classics.

New year, new experiences, right? For newbie Chicago visitors, there are must-do classic stops that represent the best of the city; for those who’ve been there, done that, check out our eight worthy alternatives.

 The Second City

Like This? The Second City

Legendary theater that’s seen greats including Steve Carell and Tina Fey. 1616 N. Wells St., 312.337.3992,

Try This: Under The Gun Theater

Featuring provocative parody shows such as “Matt Damon." 956 W. Newport Ave., 773.270.3440,


Like This? Art Institute of Chicago

With masterpieces including George Seurat’s “A Sunday on La Grande Jatte.” 111 S. Michigan Ave. 312.443.3600,

Try This: Hyde Park Art Center

Always pushing the contemporary art envelope. 5020 S. Cornell Ave., 773.324.5520,

 Skydeck Chicago

Like This? Skydeck Chicago

It’s really not a first-time trip to Chicago if you don’t make it to the top of the city’s tallest building. 233 S. Wacker Dr., 312.875.9696,

Try This: Chicago Helicopter Experience

Because the only way to get Instagram shots this amazing is to get above Chicago. 2420 S. Halsted St., 312.967.8687,


Like This? Sephora

A makeup maven’s heaven. 520 N. Michigan Ave., 312.494.9598,

Try This: Bravco

An anomaly on Oak Street amid luxe boutiques, this stalwart takes cash or checks only for its neatly jam-packed selection of beauty supplies. 43 E. Oak St., 312.943.4305,

 La Perla

Like This? La Perla

Pretty little underthings are the ultimate luxury. 34 E. Oak St., 312.494.0400,

Try This: Journelle

Where you can find La Perla, and a bevy of other high-end lingerie. 1725 N. Damen Ave., 312.471.1386,


Like This? House of Blues Chicago

A rock hall in the center of everything. 329 N. Dearborn St., 312.923.2000,

Try This: Double Door

A Wicker Park neighborhood haunt that’s sinfully cool. 1572 N. Milwaukee Ave., 773.489.3160.

Chicago History Museum

Like This? Chicago History Museum

A fascinating trip through the city’s life. 1601 N. Clark St., 312.642.4600,

Try This: Driehaus Museum

Housed in a mansion from the 1890s Guilded Age of Chicago, with period furnishings and an impressive array of Tiffany glass. 40 E. Erie St., 312.482.8933,


Like This? The iO Theater

Windy City’s top spot for long-form improv. Four stages in its expanded home mean multiple performances nearly every night. 1501 N. Kingsbury St., 312.929.2401,

Try This: Zanies

An Old Town fave for standout standup. 1548 N. Wells St., 312.337.4027,

Maggie Daley Park

New Green Space

Millennium Park still rocks it in winter, but Chicago has a new park for exploring. Maggie Daley Park, the city’s newest outdoor attraction, officially opened in 2015 and has quickly become the new “it” park. Most of the draw is during summer for wavy walking paths with cityscape views, giant climbing walls, and the popular (to the point of crazy) playground with slides, tunnels, quiet picnic groves and an “enchanted” forest. But it’s no less enchanting in the winter, when the curved walkway turns into a super-cool ice skating ribbon. 337 E. Randolph St., 312.552.3000,

Sarah Perkins
About the author

Even though she grew up in a small suburb north of Chicago, Sarah knew she was meant for somewhere bigger, more excit...