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Chicago City Trip

Chicago's impressive skyline rises above the shores of Lake Michigan
The Chicago Skyline

72-Hours in Chicago

by Jennifer Olvera


Chicago has long been subject to stereotypes including ones of the SNL variety. Pay one visit, though, and you'll quickly see it's the whole package. Truly, 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 — and food-centric — towns, Chicago is home to countless trailblazing chefs: Rick Bayless, Paul Kahan and Grant Achatz, to name a few, and they have planted the city firmly on the culinary map. Whether you're talking about internationally recognized chefs — like Marcus Samuelsson (Marc Burger) — or buzzed-about Bill Kim (Urbanbelly, Belly Shack), Graham Elliot (graham elliot) or "Top Chef" winner Stephanie Izard (Girl & the Goat), who have made haute food accessible, there's no end to what's delish.

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 cast members of aforementioned "Saturday Night Live." Meanwhile, Chicago's blues joints — a hotbed for artists like Muddy Waters and John Lee Hooker, and an inspiration for Chicago's own Blues Brothers — are legendary. And as for its dining scene, well, few foodies would argue the city's merit.

Sable Bar at the Hotel Palomar Chicago offers stylish drinks and bites
Sable Bar Lounge

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. Naturally, that spirit extends to kitchens citywide. Sustainable, locally minded menus — served in environmentally friendly spaces — abound. And the city's highly touted, chef-populated Green City Market? It's legendary — for good reason.

Not surprisingly, Chicago has no shortage of outstanding hotels, but if you're looking to stay ahead of the curve, we suggest staying at centrally located JW Marriot Chicago, where you can grab a bite at restaurant The Florentine. Other considerations include the hip, boutiquey Hotel Palomar, anchored by stylish Sable Kitchen & Bar, and the Radisson Blu Aqua Hotel, which is tucked right off of Millennium Park.

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.

CHICAGO DAY 1: Museum of Contemporary Art, The Art Institute of Chicago and Sears Tower Skydeck

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.

Tony Mantuano's Terzo Piano in Chicago serves 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.

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, or grahamwich, Graham Elliot's ode to inexpensive hand-helds. 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 haunt. Craving something sweet? Queue up at Brendan Sodikoff's mad-popular Doughnut Vault. But get there early, because when the piping-hot wonders run out, you're out of luck.

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 in Chicago provides sweeping views across the city
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.

Now that you're on a roll, it's time to take in some of the city's legendary nightlife. Most Chicagoans would tell you blues and jazz are where it's at. Although there are more frequently treaded spots like Buddy Guy's Legends and Green Mill, for our money Kingston Mines is the place to go for a non-stop tune fest. Live music is kicked out on two stages every night, and the cover charge is surprisingly affordable.

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

Alternately, opt for the best of both worlds — solid snacks and primo people watching — at Longman & Eagle in Logan Square, teaming Jared Wentworth's duck rillettes or shareable sweatbreads with Jonah crab fondue and selections from the extensive whisky and seasonal, craft cocktail lists.

Continue to Day 2


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Downtown Chicago

* Skyline image by the Chicago Convention and Tourism Bureau

(Updated: 08/06/13 CT)

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