Insiders' Chicago: From the Travel Office

The shopping mecca of Michigan Avenue, the Art Institute of Chicago and the uber-crowded Taste of Chicago festival are some of the more well-known attractions the city offers. But there is so much else to enjoy in what Carl Sandburg dubbed the "City of Big Shoulders," from touring hidden architectural gems and shopping independent designer boutiques to dining at locals' favorite restaurants. The Andrew Harper Travel Office, along with a few of our Andrew Harper Alliance hotels, share tips and insiders' secrets for getting the very most out of a visit to Chicago.

When are the best times to visit Chicago, and why?

Andrew Harper Travel Office: Joe Colucci recommends May, June, September and October for stellar weather and abundant street festivals. Music is offered year-round. The Chicago Blues Festival occurs in June, the Chicago Folk & Roots Festival is in July, and Millennium Park is home to a free classical series during the summer. September brings the Chicago Jazz Festival and two favorite foodie fests, the Windy City Wine Festival and Chicago Gourmet. December is great if you enjoy cold weather and holiday shopping, notes Jan Smart, adding, "The city is beautifully decorated in preparation for the holidays and Michigan Avenue is magnificent during the Christmas season." Colucci adds that between Thanksgiving and Christmas Eve, Christkindlmarket transforms Daley Plaza into a German Christmas wonderland. Shoppers browse, snacking on authentic German food and drink. For sports fans, Megan Leininger says the best times to visit are when the Blackhawks, Bulls, Bears, Cubs and White Sox are playing home games at various Chicago venues that include historic Wrigley Field.

If you had only three days in Chicago, which sights and activities would make it onto your itinerary?

Andrew Harper Travel Office: Colucci suggests a Shoreline Sightseeing architectural cruise and two half-day trips to the Art Institute of Chicago, one to enjoy its masters' collection and the second to explore The Modern Wing. A stroll down Michigan Avenue (the Magnificent Mile) and a stop at Millennium Park, "one of the city's most gorgeous bits of urban planning," also top his short list. While there, don't miss the Cloud Gate sculpture, locally known as "The Bean," a stunning site-specific work, says Colucci. Additional staff must-dos include visits to the family-friendly attractions at Navy Pier, the Shedd Aquarium, the 1,353-foothigh Skydeck Chicago and performances at the Chicago Shakespeare and Lyric Opera theaters.

How can architecture buffs best spend their time in Chicago?

Andrew Harper Travel Office: Shoreline Sightseeing tours, which depart from Navy Pier, offer a fun, relaxing way to learn about some of the city's best architecture, from landmark skyscrapers to hidden gems, Colucci says, adding, "I've done four or five of these cruises and learn something new every time." Joyce Jorden recommends the Chicago Architecture Foundation's walking tours. Among more than a dozen tours are trips to see the Sheffield Historic District, Logan Square and Lincoln Park Zoo architecture. Colucci says Frank Lloyd Wright fans shouldn't leave without visiting leafy Hyde Park and touring Robie House, a Wright-designed masterpiece.

What are your favorite markets?

Andrew Harper Travel Office: The Randolph Street Market includes one of the city's best antiques markets, Colucci says, as well as an independent designers' market featuring fashion, jewelry and décor. For more home décor and fashion, as well as food, check out the once-monthly Dose Market at the East River Art Center, adds Jordan. Chicago Hotels: Kristen Klus, concierge at the Four Seasons Hotel Chicago, loves the Green City Market, held in Lincoln Park. Max Schroeder, director of corporate sales at The Peninsula Chicago, agrees. "Many chefs, including ours, attend to purchase the freshest organic and unique, locally grown items right from the farmers."

Which museums should art lovers be sure to visit?

Andrew Harper Travel Office: While the Art Institute of Chicago and the Museum of Contemporary Art may top most art enthusiasts' must-see lists, several excellent smaller museums are also worth visiting, Colucci notes. He recommends the Museum of Contemporary Photography, the Oriental Institute and the National Museum of Mexican Art. Chicago Hotels: The Richard H. Driehaus Museum is "one of my favorite little-known treasures in the city," Klus says. The 19th-century home is one of Chicago's most grand, and features the Driehaus Collection of Fine and Decorative Arts. Schroeder says he frequents art studios and galleries in local neighborhoods and uses the online resource Chicago Gallery News to find them.

Where is Chicago's best shopping?

Andrew Harper Travel Office: Michigan Avenue may be where to find major retailers' flagship stores, such as those of Prada, Cartier, Crate & Barrel and Best Buy, but nearby Oak Street features numerous small, upscale boutiques, Colucci says. More shops featuring gifts, shoes, clothes and home décor can be found on Armitage Avenue, adds Carol Bacon. Smart recommends Halsted Street and Webster Avenue. Chicago Hotels: Klus says to look to the Wicker Park and Bucktown neighborhoods for Chicago's best shopping, from high-end children's items to the best vintage finds. Schroeder recommends the Andersonville neighborhood, with its small-town feel, for upscale thrift stores and unusual housewares and clothing.

What should families traveling with small children not miss?

Andrew Harper Travel Office Colucci says perennial favorites include The Field Museum, the Museum of Science and Industry and the Shedd Aquarium (crowded on weekends). Don't miss a trip to the Lincoln Park Zoo, says Jorden, or the Clarence Buckingham Memorial Fountain in Grant Park at night. Harper staffers also suggest American Girl Place, where children design their own dolls; and Navy Pier's Chicago Children's Museum, 150-foot Ferris wheel and summertime fireworks.

What are your favorite restaurants?

Andrew Harper Travel Office: Shanghai Terrace in The Peninsula tops Colucci's list for its "flawless service and exquisite Chinese cuisine." He's also fond of Moto and In Fine Spirits. Smart recommends the Gene & Georgetti steakhouse for a traditional Chicago experience. Bacon says don't miss North Pond for its lovely Lincoln Park setting and farm-to-table tasting menu. Jorden's top picks are Rick Bayless's Mexican restaurant, Topolobampo, and Girl & The Goat, adding that reservations at both are a must.

How would you spend a perfect night on the town?

Andrew Harper Travel Office: For a romantic evening, the Odyssey Dinner Cruise offers great food and service, live music and dancing with a gorgeous view of the Chicago skyline, notes Leininger. Smart says her perfect evening includes a nightcap in the Signature Room on the 95th floor of the John Hancock Center. Chicago Hotels: Klus says her ideal night begins with drinks on the terrace at the Chicago Cut Steakhouse while enjoying the beautiful Chicago River and its trestle bridges, then an authentic Italian dinner at Riccardo Trattoria, at its cozy neighborhood location. End with live music at the Green Mill, "the most nostalgic and authentic jazz club in the city."

What are the most exciting recent changes in the city that travelers will notice?

Andrew Harper Travel Office: The redevelopment of Block 37, in the heart of Chicago's downtown Loop, has transformed the area, Colucci says. It features an eclectic mix of shopping, dining and entertainment within a five-story atrium. He adds that the opening of the Elysian Hotel offers travelers a new, elegant boutique option for city lodging. Chicago Hotels: The proliferation of public art is a noticeable change, Klus says, with sculptures found throughout the Loop and downtown areas. Schroeder notes that Chicago is now bike-friendly, with 18 miles of paved bike trails along Lake Michigan and bike lanes on city streets. Bike rentals are available from vendors such as Bike & Roll Chicago. "Seeing Chicago via bike is a great way to experience the city," Schroeder says.

Originally published in the October/November/December 2011 Andrew Harper Traveler