Romantic Attractions in Chicago

  • 01 of 08

    Tour Chicago Via Lake Michigan

    Chicago beachfront
    ••• The extensive Chicago beachfront. Choose Chicago.

    When you first come into Chicago, one of the best ways to get a handle on the city is by touring it. Located right on Lake Michigan, Chicago affords visitors the opportunity to experience it via water.

    A variety of boat tours is available, including architectural tours on the Chicago River, lunch and dinner cruises, fishing charters, and lake excursions that array Chicago's must-sees before you — and help you to devise your own must-see list.

    Explore Chicago's Most Romantic Hotels

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  • 02 of 08

    Picasso Statue

    chicago picasso
    ••• Chicago's larger-than-life Picasso sculpture. Choose Chicago.

    Is it a dog? A sphinx? A former lover? A fantastical creature from the mind of Pablo Picasso? Decide for yourselves.

    The Picasso statue of Chicago, located in Daley Plaza in the Loop Area, has become a popular meeting spot for Chicagoans. Depending on the season, there are musical performances, farmer's markets, and other Chicago gatherings in the shadow of the Picasso statue.

    And that piece of art is just the tip of the iceberg. Culture lovers all deem Chicago a must-see. You'll also want to experience Anish Kapoor's "Cloud Gate" (aka the Bean), a reflection on the city and us created for Millennium Park.

    The downtown Museum Campus is home to three wonderful Chicago museums: The Field Museum of Natural History, The Shedd Aquarium, and the Adler Planetarium. (Do call ahead to avoid visiting during school trips.)

    Fans of painting and sculpture can feast on the collections in Chicago's internationally renowned Museum of Contemporary Art and the Art Institute of Chicago.

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  • 03 of 08

    Shopping

    macy's Chicago
    ••• The former Marshall Field department store was bought by Macy's. Choose Chicago.

    Bring plenty of money (or plastic) on a shopping trip to Chicago.

    From State Street to the Magnificent Mile, there's world-class shopping to be done in department stores, boutiques, gift shops, and other shopping spots in Chicago neighborhoods.

    Just don't expect to troll the aisles of venerable Marshall Field's. Macy's took over this Chicago shopping landmark in 2006.

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  • 04 of 08

    Dining

    dining out chicago
    ••• When the weather's good, couples choose outdoor dining. Choose Chicago.

    What do you hunger for? With 77 different neighborhoods in Chicago, visitors can find a wide variety of ethnic foods to sample.

    If you're on the Magnificent Mile, Foodlife in Water Tower Place — a must-see on its own merits — provides sustenance to shoppers with more than a dozen eateries.

    Of course, there are certain things you must try when dining in Chicago: The city is famous for its deep-dish pizza. And you can never go wrong if you order a steak.

    If you must see a great view when dining, make a reservation to eat in the 95th-floor Signature Room atop the John Hancock Building, which provides panoramic views of the cityscape and Lake Michigan.

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  • 05 of 08

    Chicago Nightlife

    Can you hear it? That's the sound of America you hear in Chicago, and it ranges from New Orleans zydeco to Mississippi blues to bebop to big band music. And you can hear it live in Chicago's great jazz and blues clubs.

    You'll also hear the sound of laughter in Chicago, where Old Town's Second City has been a part of the nightlife for 50 years and is a must-see on a visit. It's where Bill Murray, John Belushi, Dan Aykroyd, Gilda Radner, Mike Myers, and Chris Farley and other bust-our stars from Saturday Night Life all started, and you can discover tomorrow's comedians performing there today.

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  • 06 of 08

    Chicago Jazz Festival

    Top talents come to town for the annual Chicago Jazz Festival and perform in multiple venues throughout the city.

    To find out about the dates of the next Chicago Jazz Festival, see the schedule of events, and read about other activities visit the Chicago Jazz Festival website.

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  • 07 of 08

    Wrigley Field

    wrigley field
    ••• Where baseball's loyalists convene. Choose Chicago.

    You don't have to be a fan of the Chicago Cubs to attend a game in Wrigley Field, although it certainly helps.

    Built in 1914, Wrigley Field is the second-oldest ballpark in the major leagues (right behind Boston's 1912-era Fenway Park), and its original scoreboard still stands.

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  • 08 of 08

    Chicago's Coastline

    It’s hardly surprising that Chicago, home of the world’s first skyscraper and the tallest building in the United States (Sears Tower) should attract fans and students of architecture.

    With a breathtaking skyline, Chicago must-sees are almost too numerous to mention. The distinctive ornamental buildings of Louis Henry Sullivan and the clean, Prairie style of Frank Lloyd Wright ought to top of first-time visitors' lists, though.

    But don't think for a minute that Chicago is all steel and concrete: The city boasts 29 miles of lakefront, which includes beaches and parkland with jogging and cycling paths.

    Could Chicago be your kind of town?

    Explore Chicago's Most Romantic Hotels