Virgin or Veteran? Our Chicago Guide for First-timers and Experienced Travelers

For newbies to Chicago, the city’s their action- and attraction-packed oyster. Jaded know-it-alls, on the other hand, may think they’ve been there, done that. But our must-dos for first-timers and 50th-timers prove there’s no one-size-fits-all for Chicago

For newbies to Chicago, the city’s their action- and attraction-packed oyster. Jaded know-it-alls, on the other hand, may think they’ve been there, done that. But our dozen must-dos for first-timers and frequent visitors prove there’s no one-size-fits-all map for exploring the Windy City. 

Chicago for Virgins: What every first-time visitor needs to do in Chicago

#1: Impressionist Galleries

Art Institute Chicago
Seurat's "A Sunday on La Grande Jatte" (Courtesy Art Institute of Chicago)

Devote a day to the Art Institute and there will still be galleries left undiscovered. The don’t miss? Georges Seurat’s “A Sunday on La Grande Jatte,” displayed in all its Pointillist prominence at nearly 12 feet by 10. It’s one of many highlights of the Art Institute’s incomparable collection of Impressionist works that began with a handful of pieces brought from Europe in the late 19th century by Bertha Palmer (wife of hotelier Potter Palmer). Other eye-catching stunners include “Stacks of Wheat” paintings by Monet, Toulouse-Lautrec’s “At the Moulin Rouge” and “Bathers by a River” by Matisse. 111 S. Michigan Ave., 312.443.3600,

#2: Hop on and Hop Off Trolley Tour

There’s a lot to cram into a visit to the Windy City, but this tour makes it a breeze, allowing you all day to experience 14 top spots. Hop a trolley or double-decker bus at the Hancock Center and step off at the Field Museum for a few hours of dinosaurs, mummies and ancient civilizations, then jump back on to head to Navy Pier for a spin around the giant Ferris Wheel. Tour operators are actors and comedians first, drivers second, so expect entertaining commentary along the route. Tickets are sold at all stops: $35; seniors $25; children $17 (discounts online). 773.648.5000,

#3: The Bean

The Bean
(Photo City of Chicago/Walter Mitchell)

Millennium Park has plenty of worthy attractions, and the most magnetic is hands-down the brightly polished stainless steel “Cloud Gate,” nicknamed “The Bean” for its legume-like shape. Measuring a whopping 66 feet long and 33 feet high, the riveting reflections of people, buildings, sky and ground get cameras a-clicking. Walk under the 12-foot arch for especially fun, warped perspectives. 201 E. Randolph St., between Michigan Ave. & Columbus Ave., 312.742.1168,

 #4: Jazz Institution

The Green Mill
(Courtesy The Green Mill)

Like a lighthouse beckoning stranded ships to safe shores, The Green Mill—marked by a retro green neon sign—is a beacon on an otherwise fairly desolate (but gentrifying) strip in Uptown. Inside, hunker down for the night in one of the horseshoe-shaped booths for some serious jazz, or the weekly poetry slam on Sunday nights. A word to the curious: Yes, it’s true that Al Capone used to hang out here (although the club was actually managed by one of his co-horts, Jack McGurn), but leave that conversation for after the set; the manager WILL shhh you when the music is playing, especially if you walk in late. 4802 N. Broadway Ave, 773.878.5552,

#5: Popcorn, Hot Dogs and Pizza

Lou Malnati's
(Photo dyobmit/Creative Commons)

Chicagoans aren’t bashful about asking for second or third helpings, so don’t worry, your love handles and muffin tops are totally welcome here. A playlist of must eats might go like this: a tin of the Chicago Mix (CaramelCrisp plus CheeseCorn flavors) at Garrett Popcorn (the Mag Mile location will likely be packed, so try sister locations at the Merchandise Mart or Ogilvie Transportation Center near the Loop). For lunch, a Chicago-style dog with all the fixins—mustard, relish, tomato, poppy seed bun and so on—at Portillo’s (100 W. Ontario St., 312.587.8910), just a few blocks off The Mag Mile. Round out the local diet at Lou Malnati’s (439 N. Wells St., 312.828.9800), whose buttery, deep-dish crust is so craved that some out-of-towners have it shipped to their homes. 

#6: Architecture Tours

Wendella Boat Tour
(Photo Wendella Boats)

If you can only fit one activity into your Chicago itinerary, please take an architectural boat tour. Once the weather breaks in April, Shoreline Sightseeing, Wendella Boats and Chicago Line Cruises all conduct them from either the foot of the Wrigley Building or Navy Pier, and even the locals learn something new each time they board (e.g. That is real gold leaf atop the Carbide & Carbon Building, the home of the Hard Rock Hotel Chicago.). Mystic Blue and Odyssey Cruises also host a variety of cruises. 


Chicago for Veterans: Must-visit stops for experienced travelers

#1: 360-Degree Perspective

(Courtesy SkyDeck Chicago)

You’ve done it all—Millennium Park, Navy Pier, the John Hancock Observatory. But have you ever straddled the skyline on the Ledge, a glass balcony 103 floors up at Willis Tower? You can breathe easy; the structure is indeed well supported, and the views of the lake, skyline and four states are ever so worth the bragging rights and profile pics. 233 S. Wacker Dr.,

#2: Cultural Gem

Tiffany Dome
(Courtesy Chicago Cultural Center)

With flashy new attractions nearby and a shopping paradise up the road, the 1897 Beaux-Arts Chicago Cultural Center often gets overlooked, but we say take note: It boasts the world’s largest stained glass Tiffany dome, among other exquisite handcrafted decor, and we truly love it for its endless offerings of free and inexpensive exhibits and performances, like the ongoing “Chicago Landmarks Before the Lens,” depicting black-and-white images of 24 of the city’s historic buildings and districts. 78 E. Washington St., 312.744.3316,

#3: Historic Hotel Tour

Guests and non alike have the privilege of touring the Mag Mile’s magnificent InterContinental Hotel, built in 1929 as the Medinah Athletic Club, replete with Roaring Twenties glitz and glamour—Spanish Majolica tile, crystal chandeliers, intricate wood carvings, knights in shining armor (seriously). After meticulous historic renovation, it got its new lease on life. Simply pop over to the concierge desk for a complimentary, self-guided iPod tour and explore. 505 N. Michigan Ave., 312.944.4100,

#4: Secret Garden

Lurie Gardens
(Courtesy Millennium Park)

Beyond the limelight of Millennium Park’s big, bold public art lies a peaceful corner of understated natural beauty. The Lurie Garden is separated from the city bustle by a 15-foot-high hedge of conifers and deciduous trees, serving a practical purpose as well as poetic reference—i.e. Carl Sandburg’s description of Chicago as a “City of Big Shoulders.” Within, it’s a thoughtful, but unfussy array of perennials, shrubs, grasses and trees, as well as seasonal splendor—for spring, tulips, cherry blossoms, daffodils and shooting stars. Between Michigan and Columbus avenues, 312.742.1168,

#4: Urban Marketplace

Randolph Street Market
(Courtesy Randolph Street Market)

Mag Mile sprees are convenient (After all, who doesn’t like a Burberry, Apple Store and Nike flagship within walking distance?), but there’s an e-commerce site for all that stuff. Stroke the local economy—and your relatives’ egos—with only-in-Chicago finds from Randolph Street Market. $8 advance purchase, $10 at the gate. 1340 W. Washington St.,

#6: Chefs-in-Training

Chicago is a bona fide culinary capital, meaning the next “it” restaurant is the one you haven’t been to yet. But great chefs have to start somewhere, right? So treat yourself to Michelin-recommended deliciousness at The Dining Room at Kendall College, which became the first culinary school to receive Certified Green Restaurant status from the Green Restaurant Association for sourcing its seasonal veggies from its own herb garden and the nearby Green City Market. Bonus points for the jaw-dropping skyline views, the heavyweight visiting chef instructors (like former Aria chef and Kendall alum Beverly Kim) and a prix-fixe option for lunch ($18) and dinner ($29). 900 N. North Branch St., 312.752.2328,