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Chicago Travel Guide

Walking around the historical center of Chicago, which locals call the Loop, you’ll find your gaze drawn inexorably upward. All around you are some of the most striking and diverse architectural styles in America. Just as your eye catches an elaborate Art Deco detail in one direction, you’ll spot an ultra-modern tower in the other. Old mingles with new in what amounts to a living museum of buildings from the second half of the 1800s to the present.

Chicago doesn’t have mountains like Denver or beaches like Miami; it has buildings. Sure, as the nation’s third largest city, Chicago serves up world-class attractions like museums, an active arts scene and championship sports teams — as well as homegrown favorites like deep-dish pizza, Oprah and the Blues Brothers. But it’s in architecture that the Windy City really shines.

This is, in fact, the birthplace of the modern building. The world’s first skyscraper, the Home Insurance Building, was built here in 1885, and while that building was taken down in the 1930s, Chicago is today home to three of the tallest buildings in the world: the Willis Tower (formerly known as the Sears Tower, it stands at 1,450 feet), Aon Center (1,136 feet) and John Hancock Center (1,128 feet). Head up to the Willis or Hancock observation decks and you’ll look down over a city shaped by architectural innovators like Daniel Burnham, Louis Sullivan, Mies van der Rohe and Frank Lloyd Wright.

Chicago did not start off on such a grand scale. The city was founded at the mouth of the Chicago River in 1779 by Jean Baptiste Point du Sable, a fur trader believed to be from Haiti. But by 1848, with the completion of the 100-mile Illinois and Michigan Canal connecting the Chicago to the Mississippi, this little trading post was on its way to becoming a major transportation hub. The “Great Chicago Fire” in 1871 dealt a devastating blow, but the city rebuilt with the help of pioneering architects like Burnham, whose motto “Make no little plans” was well embraced.

Chicago is at its most impressive along the “Magnificent Mile” portion of North Michigan Avenue, where visitors will delight not only in the upscale shops but also such striking attractions as the neo-Gothic Tribune Tower, home of the Chicago Tribune newspaper, and the Beaux-Arts Wrigley Building. To see how the design innovation continues, check out the work of renowned contemporary architect Frank Gehry at Millennium Park, which has become an indelible part of the downtown core.

Downtown Chicago has the largest business district in the U.S. outside of Manhattan, and it’s all hustle and bustle. The streets fill with people at lunch hour when all the office towers seem to spew forth their occupants. But beyond the mayhem are artsy and ethnic neighborhoods, beautiful parks and the expansive shores of Lake Michigan.

Civic and ethnic pride reigns supreme. The Windy City is home to the world’s largest Polish population outside of Warsaw, and famously dyes the Chicago River green each year in celebration of St. Patrick’s Day. Visitors are often surprised to find this big, brash city a very friendly place. You’re almost guaranteed to discover, as in the song, that Chicago is your “kind of town.”

Chicago Attractions

Millennium Park is 24.5 acres and right downtown (on Michigan between Randolph and Monroe Streets) on land previously owned by the Illinois Central Railroad. World-class music, art, architecture and gardens merge here. On warm, sunny days, kids soak in an interactive fountain designed by Barcelona artist Jaume Plensa, which features two 50-foot-high glass block towers and a reflecting pool. Another sculpture, Cloud Gate by British artist Anish Kapoor, draws crowds who come to look at the elliptical reflection of the skyline in the jellybean-shaped sculpture’s polished stainless steel (it’s gained the nickname “the Bean”). In winter there’s ice skating, while warmer weather brings free concerts at the Jay Pritzker Pavilion, designed by Frank Gehry.

There are many tours of Chicago’s must-see architectural sights, but our favorites are those offered by the Chicago Architecture Foundation. There are guided tours by bus and on foot, but our favorites are the boat tours on the Chicago River (offered from spring through fall) for a unique perspective on structures like the 90-acre Merchandise Mart. You can go the self-guided route by purchasing a detailed map at the CAF’s headquarters in the historic Railway Exchange Building, where you’ll also find an excellent gift shop.

Families and nature lovers won’t want to miss a visit to the Shedd Aquarium. Permanent exhibits at the Shedd include the kid-friendly Polar Play Zone (don’t miss the penguins!) and the Wild Reef, where floor-to-ceiling windows let you view sharks, stingrays, eels and more. Be warned that the line to get in can stretch out the door and down the steps; get there when it opens to try to beat the crowds.

Got kids in tow, or feel like acting like a kid yourself? Don’t miss a visit to the lakefront Navy Pier, a 1916 landmark that’s been reborn as a venue of shops, restaurants, gardens and entertainment attractions — including a 196-foot Ferris wheel and an IMAX theater. The Pier is also home to the Chicago Shakespeare Theater and the Chicago Children’s Museum, where the mostly hands-on attractions include a Climbing Schooner kids can explore. Boat tours of Lake Michigan are offered from spring through fall.

Dinosaur fans shouldn’t miss a stop at the Field Museum, home of Sue — the largest, most complete and best preserved Tyrannosaurus rex fossil ever discovered. The Field also boasts mummies, Egyptian tombs, a Maori meeting house, and millions of examples of anthropology, botany, geology and zoology.

A favorite place for visitors to pose for vacation photos is with the lion sculptures guarding the front steps of the Art Institute of Chicago. Once you get past the beasts, you’ll find in the massive Beaux-Arts building one of the top art collections in the world with works from 3000 B.C. to the present. A highlight is the Impressionist and Post-Impressionist collection with works by Monet, Renoir, Degas, Van Gogh, Gauguin, Seurat and others. The Art Institute was expanded in May 2009 with a glass, steel and limestone wing designed by architect Renzo Piano.

The coolest thing about the Lincoln Park Zoo is that it’s one of the few remaining zoos that’s still free. Open every day of the year, the zoo is home to hundreds of mammals, reptiles and birds, and is a nice place for a stroll, not far from downtown.

The National Museum of Mexican Art, located in the lively Pilsen neighborhood, has one of the nation’s largest collections of Mexican paintings, sculptures, prints, folk art, textiles and photography.

Oak Park lays claim to not one but two of Chicago’s famous 20th-century figures. You can tour architect Frank Lloyd Wright’s home and studio, and see several examples of his famous Prairie School style, in this leafy residential neighborhood. Just a few blocks away is the birth home of Ernest Hemingway. Don’t miss a stop in the small Ernest Hemingway Museum to learn about the literary giant’s life and loves.

Baseball fans should take in a game at the legendary Wrigley Field, built in 1914. (It’s the second oldest ballpark in the country, behind Boston’s Fenway.) Can’t get tickets to a game? Take a stadium tour for a look behind the scenes.

About 25 miles west of Chicago, the 1,700-acre Morton Arboretum is one of the state’s most popular public gardens. The arboretum’s walking trails take you past highlights such as the towering Millennium Oak (it’s more than 250 years old), the flower-filled Schulenberg Prairie and the Maze Garden (if you’re not up for navigating the labyrinth yourself, you can climb to a lookout platform and watch other visitors fumble their way through the maze).

Chicago Restaurants

Chicago’s culinary scene goes way beyond deep-dish pizza, although that treat is certainly worth trying. A lesser-known favorite here is the Chicago-style hot dog, an all-beef, boiled dog eaten with mustard, sweet relish, onions, hot peppers, a pickle and tomato on a poppy seed bun. Chicago claims the title of candy capital as home to the Tootsie Roll and Fannie May Candies. And let’s not forget its status as headquarters for the number one restaurant company in the U.S. — McDonald’s.

Pizzeria Uno, the king of deep-dish pizza, is where it all began in 1943. Visit the original venue at 29 E. Ohio Street, or, if it’s busy, try sister venue Pizzeria Due at 619 N. Wabash Avenue (which has the same food in a larger space). Be aware that it takes about 45 minutes to prepare a deep-dish pie. To qualify as deep-dish, the crust has to be an inch or more thick and piled high with cheese and tomato sauce and your choice of extras — we usually go for the sausage, onion and peppers. Chicagoans also like the pies at Gino’s East, the newer kid on the block with only 50 years in the biz.

It’s worth a cab ride from downtown to Greektown, where we make a beeline to The Parthenon, opened in 1968. The place serves excellent garlicky moussaka and other Greek favorites including saganaki cheese flamed with brandy (the waiters dramatically light the cheese and shout “Opa!“). Portions are huge.

Meat lovers flock to the original Morton’s of Chicago, opened in 1978, where the ambience is club-like and the USDA prime aged steaks are huge. There’s seafood here too, like Alaskan king crab legs and jumbo lump crab cakes. Sides include creamed spinach (our favorite).

Da Bears and da pork chops are the main attractions at Mike Ditka’s. The coach’s NFL Coach of the Year trophy is on display along with other sports memorabilia. While TVs show sporting events, the food is better than the usual sports bar fare; think steaks, salads and seafood (the latter comes from sustainable and environmentally friendly sources). Da coach occasionally makes an appearance.

Good food and a convenient location near Millennium Park make Tavern at the Park worth a visit. (On sunny days, try to snag a table on the outdoor patio.) Portions are generous — the fig and prosciutto flatbread appetizer easily feeds two — and specialties include burgers, steaks, risotto, and mac and cheese.

If you’re looking not just for a meal but also for an experience, head to Alinea, which has earned three Michelin stars. Recently renoved and reopened, this Lincoln Park restaurant offers course after course of creative, impeccably plated international dishes.

Girl & the Goat draws rave reviews for its delicious small plates, ranging from goat empanadas to grilled baby octopus (with plenty of vegetarian offerings too).

Sick of continental breakfast at your hotel? Start your morning at Yolk instead. The wide-ranging menu boasts traditional options (eggs Benedict, Belgian waffles), healthy fare (the “kale scrambler”) and sweet delights (Nutella crepes, cinnamon roll French toast).

Shopping in Chicago

The Windy City’s place on the shopping map was solidified back in the frontier days when Chicago-based Sears and Montgomery Ward began sending their catalog items to homes. Marshall Field’s, opened in 1852, gave the city a pioneering department store. Today you can buy in the Windy City pretty much what you can buy in other American cities — well, maybe there are more Bears T-shirts here — but shoppers are drawn by the name brands conveniently consolidated on the Magnificent Mile, where you can find everything from Patagonia to Hugo Boss. Housewares and clothes are the big sellers. A favorite souvenir is the delectable Frango mint chocolates on sale at Macy’s (previously Marshall Field’s). Chicago also has an emerging local fashion scene that’s worth a look.

The Magnificent Mile, which runs along North Michigan Avenue from the Chicago River to Oak Street, offers hundreds of designer retail stores, shops and boutiques; it’s shopping nirvana. Here you’ll find the world’s first Crate and Barrel, as well as the very best in department stores: Nordstrom, Saks Fifth Avenue, Bloomingdale’s and Neiman Marcus. A must-do stop is the original Marshall Field’s (now Macy’s), a Chicago shopping icon which opened here in 1852 and boasts century-old clocks and a Tiffany dome; revive from shopping with a fancy lunch in the store’s Walnut Room. On the famous stretch you’ll also find a Nike store, American Girl Place and much, much more (name a popular retail brand and it’s probably on the Mile).

Fashionistas with expensive tastes will want to check out Oak Street, the place for haute designs from Paris, Milan and New York.

The hubs of the Chicago-designed fashion scene are Bucktown and Wicker Park. These artsy side-by-side neighborhoods offer a range of boutiques from ready-to-wear to couture, as well as home decor shops (contemporary and antique), art galleries and artist studios.

Upscale Lincoln Park has a mix of chain stores and independent boutiques offering everything from jewelry and women’s clothing to bicycles and vintage furniture.

–written by Fran Golden

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