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Roam Around

undefined Itinerary

Last updated: 2024 Jun 14

Morning
Start your day at the iconic Cloud Gate, also known as "The Bean," in Millennium Park. Take in the magnificent views of the city skyline while snapping some photos with the reflective sculpture. Afterwards, head to the nearby Art Institute of Chicago to see world-renowned collections of art, including works by Monet, Van Gogh, and Picasso.
Afternoon
Take a stroll down Michigan Avenue, also known as the Magnificent Mile, and shop at high-end stores like Gucci, Louis Vuitton, and Saks Fifth Avenue. For lunch, grab a famous Chicago-style hot dog at Portillo's or a deep-dish pizza at Lou Malnati's.
Evening
Head to Navy Pier for a fun-filled evening. Ride the Ferris wheel for a bird's-eye view of the city and then catch a show at the Chicago Shakespeare Theater. Finish off the night with dinner at the iconic Harry Caray's Italian Steakhouse.
Bedtime
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Morning
Start your day with a visit to the historic Wrigley Field, home to the Chicago Cubs. Take a tour of the ballpark and learn about the stadium's rich history. Afterwards, head to the Lincoln Park Zoo to see more than 1,000 animals from around the world.
Afternoon
For lunch, grab a Chicago-style Italian beef sandwich at Al's Beef or a classic Chicago-style burger at Kuma's Corner. After lunch, take a walk through the Lincoln Park Conservatory and see the beautiful collection of plants and flowers.
Evening
Catch a performance at the world-famous Second City Comedy Club, where comedians like Tina Fey and Steve Carell got their start. After the show, head to the Green Mill Cocktail Lounge for a classic Chicago-style cocktail.
Bedtime
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Morning
Start your day by visiting the Museum of Science and Industry, the largest science museum in the Western Hemisphere. Explore the exhibits on space, transportation, and technology.
Afternoon
For lunch, head to Portage Park to try some authentic Polish food at the famous Kurowski's Sausage Shop. Afterwards, visit the Frank Lloyd Wright Home and Studio in Oak Park to see the works of one of America's most famous architects.
Evening
Head to Wicker Park for a night of live music at the iconic Double Door. After the show, grab a drink at the Violet Hour, a speakeasy-style cocktail bar.
Bedtime
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Morning
Take a trip to the Chicago Cultural Center to see the stunning architecture and art exhibitions. Afterwards, visit the Field Museum to learn about natural history and see the world's largest T-Rex skeleton.
Afternoon
For lunch, head to the West Loop to try some of the city's best barbecue at Green Street Smoked Meats. After lunch, take a walk along the Chicago Riverwalk and enjoy the beautiful views of the city.
Evening
Catch a performance at the Chicago Symphony Orchestra at Symphony Center. After the show, grab dinner at the famous Italian restaurant Spiaggia.
Bedtime
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Morning
Start your day with a visit to the iconic Willis Tower, formerly known as the Sears Tower, for a bird's-eye view of the city from the Skydeck. Afterwards, head to the nearby Chicago Board of Trade Building to see the stunning art deco architecture.
Afternoon
For lunch, head to Pilsen to try some authentic Mexican food at the famous Nuevo Leon Restaurant. After lunch, take a walk through the colorful murals in the neighborhood.
Evening
Head to the historic Kingston Mines blues club for a night of live music. After the show, grab a late-night snack at the famous Billy Goat Tavern.
Bedtime
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