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Roam Around

undefined Itinerary

Last updated: 2024 Jun 14

Morning
Start your day with a visit to Millennium Park, located in the heart of Chicago's bustling downtown. Take a selfie in front of the famous Cloud Gate sculpture, also known as "The Bean," before heading to the Art Institute of Chicago to view world-renowned works of art from all over the globe.
Afternoon
After a morning of culture, indulge in a Chicago-style deep-dish pizza at Giordano's, a local favorite. Then, take a stroll down the Magnificent Mile, a stretch of Michigan Avenue that offers high-end shopping, dining, and entertainment options. Finish off your day with a visit to the John Hancock Center's 360 Chicago Observation Deck, where you can take in breathtaking views of the city from 1,000 feet above ground.
Evening
For dinner, head to Girl & the Goat, a trendy eatery where you can sample unique small plates and craft cocktails. After dinner, catch a show at the famous Second City comedy club, where many famous comedians got their start.
Bedtime
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Morning
Today, explore Chicago's diverse neighborhoods. Start with a visit to Wicker Park, a hipster enclave with unique shops and galleries. Grab brunch at The Bongo Room, known for its creative breakfast dishes and decadent pancakes. Then, head to Pilsen, a predominantly Latino neighborhood known for its vibrant street art and colorful murals.
Afternoon
After lunch at the popular taqueria, L'Patron, take a guided tour of the historic Chicago Theater, which has hosted countless iconic performances since its opening in 1921. Finish off the afternoon with a visit to Navy Pier, where you can enjoy carnival rides, boat tours, and stunning views of Lake Michigan.
Evening
For dinner, head to Alinea, a three-Michelin-starred restaurant that offers a multi-sensory dining experience like no other. After dinner, grab a drink at The Violet Hour, a speakeasy-style bar that serves up inventive cocktails in a chic, moody atmosphere.
Bedtime
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Morning
Start your day with a visit to the Lincoln Park Zoo, one of the oldest zoos in the country and home to over 1,000 animals. Then, head to the nearby Peggy Notebaert Nature Museum, which showcases the flora and fauna of the Midwest region.
Afternoon
After a morning of animal encounters, grab lunch at Lou Malnati's, another local favorite for deep-dish pizza. Then, take a stroll through the Lincoln Park Conservatory, a lush indoor garden that features exotic plants and flowers from around the world.
Evening
For dinner, head to Monteverde, a pasta-focused restaurant that has garnered national acclaim for its innovative dishes. After dinner, take a sunset architecture boat tour along the Chicago River, where you can marvel at the city's iconic skyline from a unique perspective.
Bedtime
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Morning
Today, take a trip to the Museum of Science and Industry, one of the largest science museums in the world. Explore exhibits on everything from space exploration to genetics, and be sure to catch a show at the Omnimax Theater.
Afternoon
After the museum, head to Hyde Park, a historic neighborhood home to the University of Chicago and the former residence of Barack Obama. Grab lunch at Valois Cafeteria, a legendary spot that has been visited by countless politicians and celebrities over the years. Then, take a stroll through Jackson Park, a picturesque green space that was the site of the 1893 World's Columbian Exposition.
Evening
For dinner, head to Avec, a Mediterranean-inspired restaurant that offers rustic small plates and an extensive wine list. After dinner, catch a performance at the Chicago Symphony Orchestra or the Lyric Opera of Chicago, both located in the city's vibrant Loop district.
Bedtime
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Morning
Today, take a trip to the Field Museum, one of the most popular natural history museums in the country. Explore exhibits on everything from dinosaurs to ancient civilizations, and be sure to check out the museum's famous resident, Sue the T-Rex.
Afternoon
After the museum, head to the West Loop neighborhood, one of the hottest dining destinations in the city. Grab lunch at Au Cheval, a diner-style eatery that serves up some of the best burgers and fries in town. Then, explore the neighborhood's many art galleries and boutiques.
Evening
For your final dinner in Chicago, head to Oriole, a two-Michelin-starred restaurant that offers a refined tasting menu of contemporary American cuisine. After dinner, take a stroll along the Chicago Riverwalk, a scenic pedestrian path that offers stunning views of the city's architecture.
Bedtime
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