Rising off the southern edge of Lake Michigan are the skyscrapers that immediately distinguish the midwestern city of Chicago, Illinois from the surrounding farmland. Despite its bitterly cold winters, Chicago is among the largest of the US cities and is famed for its bold art deco and modern architecture that was largely built after the city was demolished by a fire in 1871 – rumored to have been caused by an irritable cow. In the decades to follow, the city blossomed into a modern metropolis where hungry visitors can visit some of the best restaurants in the United States, or opt for a classic “deep dish” pizza.

17 places

Chicago, Illinois, United States

Congress Plaza Hotel

This 19th-century Hotel is home to 871 rooms -- and countless ghosts who roam its halls.

Chicago, Illinois, United States

Medinah Athletic Club

Once an exclusive men's club, this completely renovated hotel feels like stepping into Chicago's extravagant past.

Chicago, Illinois, United States

Palmer House

When the Palmer House opened on Chicago’s downtown Loop over 140 years ago, elevators in a hotel were kind of a big deal. In fact, Palmer House was the first hotel with elevators, electric lightbulbs, and telephones in the guest rooms.

Chicago, Illinois, United States

First Church of Deliverance

Founded in 1939, the First Church of Deliverance occupies a unique Art Moderne building designed by African American architect Walter T. Bailey.

Chicago, Illinois, United States

Avondale Bowl

Original pin setters, wood lanes, and paper score cards give this restored bowling alley an authentically retro feel.

Chicago, Illinois, United States

Bel Harbour Pool

Built in 1967, this pool deck sits on the top floor of a 30-story high rise overlooking Lake Michigan.

Chicago, Illinois, United States

Chicago Athletic Association

This former Chicago sports club counts William Wrigley among its founding members. Wrigley based the Cubs' logo on the CAA's C-shaped logo design.

Chicago, Illinois, United States

Park Gables

This Tudor Revival co-op, one of Chicago's first, contains a hidden Moroccan-style pool. It also housed a small zoo featuring common farm animals.

Chicago, Illinois, United States

Ganz Hall

Accidentally built as an afterthought, this hall is the product of famed designers and architects, including Frank Lloyd Wright, who worked as an apprentice.

Chicago, Illinois, United States

Navy Pier

This pier is one of the busiest attraction in Chicago, and even home to a World Record.

Chicago, Illinois, United States

Art Institute of Chicago

This art museum, originally intended for the 1893 World's Fair in Chicago, stands today as one of the leading fine arts institutions in the U.S.

Chicago, Illinois, United States

Walter Payton College Prep

Every March 4th, this Chicago prep school give back to the community on Sweetness Day in honor of the school's namesake, NFL Hall of Fame member Walter Payton.

Chicago, Illinois, United States

InterContinental Chicago

This hotel has one of the oldest and largest pools in the United States, showcasing classic architecture from the 1920s.

Chicago, Illinois, United States

Engine Co. 98

This Chicago Fire station, built in 1904, was inspired by medieval castles and is still in use today.

Chicago, Illinois, United States

Stony Island Arts Bank

A former savings and loan bank, this exhibition center is a hub for black art and culture.

Chicago, Illinois, United States

Lake Shore Place

This Chicago building, once the tallest in the world, was once the headquarters of Playboy Enterprises. It became known colloquially as the "New Playboy Building."

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