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Roam Around

undefined Itinerary

Last updated: 2024 Jun 14

Morning

Start your day with a visit to the famous Cloud Gate sculpture, also known as "The Bean," in Millennium Park. Then, head over to the Art Institute of Chicago to see one of the largest art collections in the country.

Afternoon

Enjoy a stroll down the Magnificent Mile, Chicago's premier shopping district, with stores like Nordstrom, Neiman Marcus, and Saks Fifth Avenue. For lunch, stop at the famous Chicago-style pizza restaurant, Lou Malnati's.

Evening

Take a sunset architectural boat tour on the Chicago River to view the city's stunning skyline. End the night with a visit to the iconic Navy Pier, where you can ride the Ferris wheel and enjoy live music.

Bedtime

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Morning

Spend the morning exploring Chicago's famous museums, including the Field Museum, the Museum of Science and Industry, or the Shedd Aquarium.

Afternoon

For lunch, head to Portillo's for a classic Chicago-style hot dog or Italian beef sandwich. After lunch, take a walk through Lincoln Park Zoo, one of the oldest zoos in the country.

Evening

Catch a Cubs game at Wrigley Field, one of the most iconic baseball stadiums in America. After the game, grab a drink at one of the many bars in Wrigleyville.

Bedtime

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Morning

Start the morning with a visit to the stunning Chicago Cultural Center, with its beautiful architecture and free exhibits. Then, head over to Grant Park to see the Buckingham Fountain.

Afternoon

Grab lunch at the famous Billy Goat Tavern, a Chicago institution made famous by Saturday Night Live. After lunch, take a walk along the Lakefront Trail and enjoy the beautiful views of Lake Michigan.

Evening

End the night with a visit to Second City, the famous comedy club that launched the careers of many famous comedians. Enjoy a show and some laughs before heading back to your hotel.

Bedtime

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Morning

Take a day trip to nearby Frank Lloyd Wright Home and Studio in Oak Park, where you can tour the famous architect's home and studio and learn about his life and work.

Afternoon

For lunch, head to the famous Portillo's for a classic Chicago-style hot dog or Italian beef sandwich. After lunch, visit the Garfield Park Conservatory, one of the largest indoor gardens in the world.

Evening

End the night with a visit to the Green Mill Cocktail Lounge, a historic jazz club that has hosted famous musicians like Al Capone.

Bedtime

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Morning

Start the day with a visit to the Museum of Contemporary Art, featuring works by artists like Jeff Koons and Andy Warhol. Then, head over to the Chicago Riverwalk for a scenic stroll.

Afternoon

For lunch, head to Rick Bayless's Frontera Grill for delicious Mexican cuisine. After lunch, head to the iconic Willis Tower (formerly known as the Sears Tower) for stunning views of the city from the Skydeck.

Evening

End the night with a visit to the Kingston Mines blues club, featuring live music every night of the week.

Bedtime

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