The best attractions and things to do in River North and Streeterville

This tourist hot spot features shops, eateries, an IMAX cinema and a bevy of sightseeing boat tours. Pier Park is home to an old-fashioned swing ride and 18-hole mini-golf course with an even larger Ferris wheel on the way. You'll also find the Chicago Children's Museum and a rotating roster of live entertainment. Most offerings may not turn locals on, but the seasonsal events, indoor activities and great people-watching provide plenty of entertainment, no matter what the weather.

The most recognizable face in the theater’s lobby might belong to old Friend David Schwimmer, but expect nothing of the sitcom variety inside the theater of this troupe. Taking its name from the hallucinatory world of Lewis Carroll, the playful company put itself on the map by mounting cirque-influenced, highly physical renditions of classic literature and myths. In 2011, Lookingglass became the fifth Chicago institution to receive the Tony Award for regional theater.

Built during the 1920s by Marshall Field & Co., Merchandise Mart is the world's largest commercial building, spanning two full city blocks and rising 25 stories high. The building houses furniture showrooms and retail shops and hosts numerous trade shows and community events each year. In 2007, the Mart was declared the largest LEED-EB (Leadership in Energy and Environmental and Design for Existing Buildings) in the world.

The second Headquarters location brings the vintage arcade fun to River North, offering a similarly large collection of games and more than 70 craft beers. This location also serves up some non-typical bar food, including gumbo. Just like in Lakeview, all the games are free to play, so you may have to jockey for a turn in front of the Ms. Pac-Man cabinet.

Housing one of the largest collections of modern art in the nation, the Museum of Contemporary Art also hosts major touring exhibits, film screenings and performing artists. When you're not browsing the extensive galleries, grab a bite to eat at the on-site restaurant or take a stroll through a picturesque sculpture garden. Don't forget to exit through the gift shop—it boasts one of the city's best selections of offbeat tchotchkes.

Presenting some of the best national and international acts through one of the city’s finest sound systems, the Chicago edition of this chain is especially beautiful (check out the plush bathrooms). Purists scorn the place, but any venue that runs the gamut from B.B. King to Crystal Castles to Tech N9ne must have something going for it. The majority of bands featured on the smaller stage are blues acts,and every Sunday the venue hosts a “Gospel Brunch.”

The Museum of Broadcast Communications has made significant progress since opening its first full display—the National Radio Hall of Fame Gallery—in 2011. In addition, interactive TV exhibits now occupy the second floor. From a replica of Lucy’s famous polka-dotted dress on I Love Lucy to a video explaining the significance of the MTV’s The Real World, this museum is made for media buffs.

In less than 20 years, this unpretentious troupe moved from the back of a Lincoln Park pub to a multimillion-dollar facility with a spectacular lake view. The main stage was modeled on Stratford-upon-Avon’s Swan Theatre. In 2008, Chicago Shakespeare Theater became the fourth Chicago institution to pick up the Tony Award for regional theater excellence. The main course here is Shakespeare, of course, but with detours into classics of every stripe, including the occasional musical.

Local headliners rule at this downtown stand-up room, which recently moved from the Ontourage nightclub to the third floor above Gino's East in River North.

The L.A. Lucky Strike is a fave on Entourage. Chicago’s is more local and less celeb, but you can still feel like one of the beautiful people downing drinks and munching good grub in the wine bar.