Photographed by Grace Willis. 
Photo: Courtesy of the Art Institute of Chicago. The Art Institute of Chicago Contemporary Galleries
The Art Institute of Chicago's gorgeous Renzo Piano-designed Modern Wing opened with a bang in 2009. But, many tourists and locals alike tend to overlook its world-class collection of contemporary art on their way to see A Sunday Afternoon on the Island of La Grande Jatte. That's a crying shame, as the Institute actually houses one of the largest collections of contemporary art of any encyclopedic museum in the world. Set aside a few weekend afternoons to take in the paintings, sculptures, installations, and new media works by such giants as Willem de Kooning, Eva Hesse, Jasper Johns, Ellsworth Kelly, Joan Mitchell, Bruce Nauman, Jackson Pollock, Gerhard Richter, and Cy Twombly (there are more than 1,000 to view). Then grab lunch at Terzo Piano and reflect on genius.
The Art Institute of Chicago, 111 South Michigan Avenue (at East Adams Street); 312-443-3600.
Smith Museum and Macy's Pedway Stained-Glass Exhibit
The Chicago Pedway is a fascinating attraction in and of itself. But, Macy's, in conjunction with Navy Pier's Smith Museum and the Chicago Cultural Mile Association, have teamed up to bring an impressive dose of, er, underground culture to the pedway. Just head down to the entrance at Macy's State Street location (picking up a box of Frango mints while you're at it), to see 22 pieces of non-religious, American-Victorian stained glass, put on permanent loan from the Smith Museum. The back-lit works were created for residences and public buildings, and include everything from portraits to abstract shapes. After strolling through the exhibit, contemplate its beauty at Macy's kitsch pedway bar, Infield's.
Macy's, 111 North State Street (at West Randolph Street); 312-781-1000.
Odd Obsession Movies
Looking for a Blu-ray edition of the latest blockbuster hit? Well, Odd Obsession may have it, but what the Milwaukee Avenue film library really specializes in is under-the-radar, independent, artistic, and otherwise obscure cinema. With 26,000 DVD and VHS titles on hand, Odd Obsession is the go-to source for Chicago cinephiles to discover a thought-provoking contemporary or classic film. And, if you don't have anything in mind, the hyper-knowledgeable staff will always have a few recs on hand.
The store, which is largely staffed by volunteers, also offers film-inspired T-shirts and posters. "If it's cult, kitsch, weird, we're pretty likely to have it," said Brown.
Odd Obsession, 1822 North Milwaukee Avenue (at West Bloomingdale Avenue); 773-276-0894.
Photographed by Grace Willis. Green Mill Capone Booth
You could write a book on the history of Uptown's Green Mill: One of Al Capone's only Northside establishments, it's arguably the last — and the best-preserved — speakeasy from the Roaring '20s. Want to know what it felt like for a wiseguy and his moll to head out for a big night out on the town in the Jazz Age? Just step into the Mill, which is pretty much the same as it was in its heyday. Perhaps most famously, it's where singer Joe E. Lewis was hired by then-owner Jack McGurn, a Capone henchmen, to perform. When Lewis tried to break away from the club for a more lucrative deal at a competitive spot, McGurn's goons slashed him to ribbons at a downtown hotel.
Amazingly, the entertainer survived, reinvented himself as a comedian, and later became one of Vegas' biggest acts — the unbelievable ordeal was fictionalized in the 1957 film The Joker is WIld, with Frank Sinatra starring as Lewis. These days, sitting in the Mill's "Capone Booth," is as close as anyone will get to the most famous Chicagoan of all. Legend has it, that’s where Al and his boys would perch so that they could check out the acts and see who was coming and going, while enjoying some world-class jazz,
The Green Mill, 4802 North Broadway Street (at West Lawrence Avenue); 773-878-5552.
Frank Nitti's Vault
You've got to hand it to Harry Caray's Restaurant Group; not only did it recently unveil the stellar, must-visit Chicago Sports Museum adjacent to its new restaurant on the seventh floor of Water Tower Place, it also has a far more mysterious, far smaller, and far more intriguing ode to another type of Chicago legend at its Kinzie Street location. As it turns out, the charming building at 33 West Kinzie Street once belonged to high-ranking Chicago Outfit (a.k.a. the mob) member Frank Nitti's in-laws, the Caravettas, and Nitti reportedly kept an apartment on the fourth floor from 1939 to 1943, when he took his own life. The real Nitti didn't have much to do with the characters made famous in the TV show or film versions of The Untouchables — he was more bookish than thuggish — but he was indeed a gangster near the very top of the Capone organization.
When the restaurant was being built out, workers found several ostensible mob-related goodies, including an address book containing the contact information for numerous reputed gangsters, hidden rooms, tunnels, and a three-door safe — all of which are available for the curious to browse in the restaurant's basement, accessible through the bar. In decidedly un-mob-like fashion, the museum is even free to customers — and is even more fun after a martini.
Harry Caray's Italian Steakhouse, 33 West Kinzie Street (at North Dearborn Street); 312-828-0966.
Photo: Courtesy of Tony Gourmet Group. Order Off-Menu at Lao You Ju
There's no doubt that Tony Hu is the final word when it comes to Chinese food in Chicago, and there's no doubt that his sleek Chinatown destination Lao You Ju is the most elegant outpost of his restaurant empire. While visiting Lao You Ju and ordering off the admirably expansive menu is a fantastic treat on its own, those seeking an even more unforgettable experience can call ahead and have the internationally renowned chef prepare a custom tasting menu for them. What's on it? Only Hu knows. And, that's the beauty of it.
Lao You Ju, 2002 South Wentworth Avenue (at South Archer Avenue); 312-225-7818.
Beyond the Score
What's better than seeing one of the world's great orchestras perform a masterpiece? Well, not much. But, the CSO's Beyond the Score series does an amazing job of bringing classical music to life in ways that both delights aficionados and appeals to those who might not even know they have an interest in the art form. Each performance is divided into two parts: The first features interactive components, creative lighting, actors, projections, original stage sets, and, of course, the orchestra that brings the history of the piece to life in a wholly original way. The second part of the show is a complete performance of a work by the CSO. Don't miss the next Beyond the Score, showcasing the work of Pierre Boulez, with stage elements by world-renowned architect Frank Gehry on November 14 and 15. (You can view previous performances here.)
If you’re planning a date, check out BTS hip POST after-party on Friday nights. Single tickets are $35, or there are three-concert subscriptions with special pricing available. Those looking to elevate the high-art quotient in their lives will also want to check out the CSO's MusicNOW series, which showcases contemporary classical music curated by CSO composers-in-residence Mason Bates and Anna Clyne. Held at the Harris Theater, the performances generally feature special lighting and other visual elements, as well as live DJ sets before the concert. The next MusicNOW, which also features an after-party, takes place on September, 29. Tickets are $25, while four-concert subscription packages with special pricing are also available.
Chicago Symphony Orchestra, 220 South Michigan Avenue (at West Adams Street); Harris Theater, 204 East Randolph Street (at South Columbus Drive); 312-294-3000.
Photo: Courtesy of the Glessner House. Glessner House Museum
Once Chicago's millionaires' row nonpareil, and home to the jaw-dropping residences of titans of industry, including Marshall Field, George Pullman, and Palmer Potter, the South Loop's Prairie Avenue sunk into stark decrepitude before bouncing back to life in recent years. These days, with many of its Gilded Age mansions restored, the six-block Chicago Landmark district is one of the most fascinating historical streets in city. While many of the remaining mansions are private residences, the stunning Glessner House, built by architect Henry Hobson Richardson for machinery magnate John J. Glessner in 1887, is a jewel of a cultural destination, showcasing not only remarkable, progressive architecture, but also 19th-century arts-and-crafts, furniture. Not everyone was a fan of the house's architecture, however. George Pullman, who lived across from it, reportedly said: "I do not know what I have ever done to have that thing staring me in the face every time I go out my door." Those who share his sentiments may instead opt for a tour of nearby Clarke House — built in 1836, and the oldest house in Chicago. The Glessner House Museum also conducts those tours.
Glessner House Museum, 1800 South Prairie Avenue (at 18th Street); 312-326-1480.
Chicago Architecture Foundation Motor Row Tour
It's no coincidence that Motor Row has become a hip near-South Side destination — with its world-class, turn-of-the-century architecture, how could it not be? But, in its heyday, the row was home to as many as 116 auto dealerships, featuring everything from still-thriving makes like Ford, Buick, Fiat, and Cadillac to defunct manufacturers such as Sears (yes, that Sears), Hudson, Locomobile (we want one), Marmon, and Pierce-Arrow. Designated a historic district in 2000, the row features 50 stunning buildings designed by the likes of Albert Kahn and Holabird & Roche. Take a Chicago Architecture Foundation-sponsored tour of the district with architecture and auto enthusiasts Bob Joynt and Dan Lempa, and learn what it was like to purchase your dream wheels back in the glory days. Tours take place twice monthly on alternating Saturdays and Sundays through October 4.
CAF Motor Row Tour, guests meet at 2222 South Michigan Avenue (and East Cermak Road); 312-922-3432.