Chicago, Illinois 72-Hour Vacation

The Chicago Skyline

Sure, it fell short of winning the Olympic bid, but that's done little to take the spotlight off of Chicago, the hippest city in the Midwest. A top dog in the dining department, it also has a killer skyline, burgeoning theater scene and world-renowned museums.

From its beginnings, the city was a culture-laden place of innovation. Now, it's also where the high brow comfortably meets the everyday, and food, architecture, sports and nightlife commingle with buzz-generating results. Rising from the ashes of the great Chicago Fire in 1871 to become one of the world's most sophisticated towns, the Second City has a dark but dazzling allure, from its one-time speakeasies and mobster haunts to its comedy clubs that launched the careers of countless "Saturday Night Live" cast members.

Needless to say, Chicago's blues joints—a hotbed for artists like Muddy Waters and John Lee Hooker, not to mention inspiration for Chicago's own Blues Brothers—are legendary. And as for its dining scene, well, few foodies would argue the city's merit. Chicago is home to trailblazing chefs—Rick Bayless, Charlie Trotter, Paul Kahan and Grant Achatz, to name a few—who have upended the dining world and planted the city firmly on the culinary map. Whether you're talking about internationally recognized chefs—like Laurent Gras (L20) or Marcus Samuelsson (C-House)—or buzzed-about Bill Kim (Urbanbelly, Belly Shack) or Takashi Yagihashi (Takashi), who have made haute food accessible, there's no end to what's delish.

theWit Hotel

In recent years, the city also has become part of the growing "green scene." Bees, which make honey and honey-based products sold at Chicago's Green City Market, buzz atop a rooftop garden above City Hall, in vacant lots and along the lakefront. From a bird's eye view lush green rooftops can be seen speckling the landscape. Even convention centers are getting in on the action: McCormick Place now boasts a LEED-certified pavilion and the Museum of Science and Industry sports a three-story modular, sustainable home to spark (and inspire) the imagination. Needless to say, that spirit extends to kitchens citywide. Sustainable, locally minded menus—served in environmentally friendly spaces—abound.

There's no shortage of outstanding hotels, but if you're looking to stay ahead of the curve, we suggest staying at newly opened, centrally located theWit Hotel—be sure to grab a bench (and a few cocktails) at its tony rooftop lounge. Another solid option is the eco-minded Dana Hotel and Spa where rain showers, Zeppelin mp3 media systems and Keurig coffeemakers are the order of the day.

Since Chicago has an excellent mass transit system of subways, elevated trains and buses, a rental car isn't necessary if you're sticking around downtown. Check out the multi-day visitor passes, which are good for unlimited rides on all the Chicago Transit Authority buses and trains. You can pick one up by calling 888-YOUR-CTA or going to a visitor information center or a main tourist attraction. Complimentary trolleys run along Michigan Avenue out to the museum area, to the Navy Pier and in the Lincoln Park neighborhood during the summer. Taxicabs also are plentiful.

Also think about buying a CityPass to save up to 50% off the price of regular admissions to some of the city's most popular attractions.

DAY 1

When spending time in Chicago, hitting a few tourist hubs is a must. The city's rich museum culture promises endless educational opportunities, and a stop at Museum of Contemporary Art is essential. Lauded for its collection of art of our time—from painting, sculpture and photography to video, performance and film—the museum offers thought-provoking art exhibitions. Its permanent collection includes works from Franz Kline and Andy Warhol. When weather permits, be sure to check out the terraced garden, which affords great views of Lake Michigan.

Of course, the comprehensive collection—particularly the array of Impressionist and American art—at The Art Institute of Chicago, is unparalleled. Originally constructed for the 1893 World's Columbian Exposition, it began as a museum and a school and remains one of America's preeminent museums and educational art institutions today. If you go this route, make your way to the recently unveiled Renzo Piano-designed, 264,000-square-foot Modern Wing, which houses European works from 1900 to 1950. Depending on how long you hang out, you might want to relax at Tony Mantuano's Terzo Piano, a sedate, stylish lunch spot serving local, organic and sustainably produced Italian fare.

Terzo Piano

Consider stopping by the International Museum of Surgical Science, too, where you'll find everything from a working metal lung to early incarnations of medical X-Ray equipment and gruesome paintings of surgical procedures. Too squeamish? Head to the Museum of Holography, a cheesy-cool spot that's home to both holographic exhibitions and a school.

When lunchtime arrives, keep things casual but cool with a stop at The Gage, Irish-born Billy Lawless' pub with upscale grub from Dirk Flanigan. Savor a single malt scotch, snag a braised rabbit salad or opt for one of its top-notch burgers. Of course, you could always head to pork and seafood-heavy hitter The Publican, a follow-up to Blackbird and Avec, or grab caldo (a warming brothy soup available after 3 p.m. only) and wood-fired tortas on Labriola bread from Xoco, Rick Bayless' Mexican street food-inspired newcomer.

Next, visit the Sears Tower Skydeck located on the legendary building's 103rd floor. Here you'll delight at the panoramic views of the city's architecture, as well as glimpses of Michigan, Indiana and Wisconsin on a clear day. Be sure to step onto the enclosed, glass-bottom ledge—if you dare. Another great view can be had at the John Hancock Observatory on the 99th floor of the John Hancock Center. But if it's simply the skyline you're looking to glean—Vertigo Sky, The Terrace at Trump and C-View among them—also offer posh perches with expansive views. Of course, if something more traditional is your thing, the Signature Room at the 95th in the John Hancock Center will more than suffice.

John Hancock Observatory

Afterward, mosey on over to Gibson's Steakhouse for some of the city's finest prime cuts, football-sized lobster tails and über-cold martinis. As if the walls decked with autographed publicity photos didn't clue you in upon your entry, you might want to keep your eyes peeled for the smattering of in-town celebrities, famous tycoons and local athletes who frequent this haunt.

More into the indie scene? Inquire about the lineup at Double Door or The Hideout.

Continue to Day 2

* Skyline image by the Chicago Convention and Tourism Bureau.