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America's Most Welcoming City

Visitors to the Windy City can expect a warm welcome as they explore must-visit sites dotting Grant Park, Museum Campus and the mall-filled Magnificent Mile. Gawk at world-renowned architecture by icons such as Frank Gehry and Frank Lloyd Wright. Dining ranges from award-winning, high-end enclaves to delicious deep-dish pizza dives.

What to Do

John Hancock Observatory
John Hancock Observatory

John Hancock Observatory

Take in a 360-degree view of the Windy City from 1,000 feet up, courtesy of the seventh-tallest building in the US. Located on Chicago’s bustling Michigan Avenue, the John Hancock Center offers views of up to 4 states (Illinois, Michigan, Indiana and Wisconsin) from its observatory deck. 960 1280

John Hancock Observatory  

Chicago Theatre

Chicago Theatre

Enjoy plays, magic shows, concerts and other performing arts at this historic theater in downtown Chicago’s historic Loop, or commercial center. Architecture buffs will also want to tour the famed 7-story landmark, which occupies nearly half a city block. 960 1280

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Navy Pier

Navy Pier

Take the kids to this 3,300-foot-long pier on the Chicago shoreline of Lake Michigan. A city fixture since 1916, Navy Pier now stands as Chicago’s No. 1 tourist attraction. Enjoy a dinner cruise, see fireworks at night, take in an IMAX movie and hop aboard the 150-foot-tall Navy Pier Ferris wheel -- Chicago was the first city in the world to erect one! 960 1280

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Wrigley Field

Wrigley Field

Take the gang out to the ballpark! Home to the Chicago Cubs since 1916, Wrigley Field hearkens back to baseball’s heyday with a jewel-box design. The ballpark is also famous for its outfield walls covered by ivy -- the only professional ballpark with that distinction -- and a scoreboard that’s still manually operated. 960 1280

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Chicago Field Museum

Chicago Field Museum

Brace yourself: These fighting African elephants go horn-to-horn at Chicago’s Field Museum. But the real star attraction at this museum of natural history is Sue, the largest, best-preserved and most complete T. rex ever found -- you’ll find this 42-foot-long, 13-foot-high beast within an exhibition on the museum’s balcony. 960 1280

Edsel Little, flickr   

Chicago River Cruise

Chicago River Cruise

If you love water and architecture, then come to Chicago. Enjoy a cruise along one of Chicago’s 2 rivers: The Chicago River cuts through downtown, weaving past dozens of skyscrapers, each a speaking to a style of architecture known as the Chicago School, which went on to become famous throughout the world. 960 1280

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Robie House, Frank Lloyd Wright

Robie House, Frank Lloyd Wright

And on terra firma, take a tour of Robie House. Designed by Frank Lloyd Wright, the building, located on the University of Chicago’s campus, is often hailed by architects as one of the most important buildings in American architecture … and a forerunner of modernism in architecture. 960 1280

mach3, flickr   

University of Chicago Tour

University of Chicago Tour

Bragging rights alert: This impressive 211-acre campus is widely considered by academics to be one of the most prestigious universities in the world. Let some of that smartness rub off with a tour of the grounds, which showcase a mixture of Victorian Goth and Collegiate Gothic architecture, as well as more modern styles. 960 1280

Henryk Sadura  

Uno Chicago Grill

Uno Chicago Grill

Oh, yeah … sink your teeth into this carb-heaven indulgence, which we know and love as the deep-dish pizza. Origins of the deep-dish are disputed -- Lou Malnati’s Pizzeria in nearby Northbrook also claims to have invented the recipe. To which, we offer 1 solution: Sample both Uno’s deep-dish, and Malnati’s -- and see which one you like the best! 960 1280

Kenyaboy7, flickr   

Taste of Chicago

Taste of Chicago

Head to the outdoor food festival Taste of Chicago, which showcases more than 70 food vendors who set up shop over a 10-day period each summer in Chicago’s Grant Park. Just imagine: Chicago hot dogs, Eli’s cheesecake and so much more! Coming in the fall instead? Grant Park is home to another great show: the annual Lollapalooza music fest. 960 1280

star 5112, flickr   

The Magnificent Mile

The Magnificent Mile

To see Chicago’s best landmarks, stroll down the Magnificent Mile. Just make sure your camera’s all juiced up: You’ll see some of America’s tallest buildings -- the John Hancock Center and the Trump International Hotel and Tower -- as well as Wrigley Building, Tribune Tower, the Chicago Water Tower and the Allerton Hotel. They don’t call this stretch of Chicago’s Michigan Avenue magnificent for nothing. 960 1280

Fraser Hall  

Lincoln Park Zoo

Lincoln Park Zoo

Some things in life really are free, and you can enjoy them any day of the year at the Lincoln Park Zoo. One of the last free-admission zoos in America, the 35-acre grounds are home to 1,200 animals, representing 230 species. Among them is this 1,700-pound polar bear, getting up close and personal with some visitors. 960 1280

Lincoln Park Zoo  

Billy Goat Tavern

Billy Goat Tavern

Feel the allure of newspapers’ glory days with a visit to this tavern. Tucked in a corner of Michigan Avenue, beneath elevated railroad tracks, the pub achieved its legendary status through newspaper columns by Pulitzer Prize-winning columnist Mike Royko. Enter at your own risk (think: Curse of the Billy Goat story) … and order a cheezborger! 960 1280

Brent Payne, flickr   

The Bean

The Bean

There’s just something about Millennium Park’s Bean; people are drawn to the sculpture’s massive shiny, mirrored surface. They come up to it, gaze at their reflections, and the city skyline’s, and take advantage of some great photo-taking ops. Go ahead, you know you want to do the same. 960 1280

  

Willis Tower

Willis Tower

Shooting 1,451 feet into the air, this 108-story skyscraper was the tallest building in the world when it was completed in 1973 -- a distinction it held for the next 25 years. Head to its Skydeck, on the 103rd floor; on a clear day, you can see across the plains of Illinois … and Lake Michigan … to Indiana, Michigan and Wisconsin. Most astoundingly, visitors can actually feel the building sway on a windy day. 960 1280

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Second City

Second City

Improv and Chicago go hand in hand -- thanks to this improvisational comedy troupe in Chicago’s Old Town neighborhood. For more than 5 decades, Second City has been a starting point for comedians, actors and directors, such as Bill Murray, who got his start here. 960 1280

Second City