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Ultimate 5-Day Chicago Adventure with Iconic Landmarks and Culinary Delights Itinerary
Last updated: 2024 Jun 14City Icons and Riverfront Marvels
Morning
Begin your Chicago journey with a breathtaking view from the 360 Chicago Observation Deck (Formerly John Hancock Observatory), followed by a delightful breakfast at Little Goat Diner. Afterward, take a stroll through the iconic Wrigley Building and marvel at the unique architecture of Marina City.
Afternoon
For lunch, savor the flavors of Xoco, renowned for its Mexican cuisine. Post-lunch, enjoy a relaxing walk along the Chicago Riverwalk, taking in the sights of the bustling city and the serene river. Conclude your afternoon at the cultural oasis of Art Institute of Chicago, immersing yourself in world-class art.
Evening
Dine at the innovative Alinea, a three-Michelin-star restaurant offering a culinary experience like no other. Afterward, take a leisurely stroll through the vibrant Millennium Park, where you can admire the famous Cloud Gate sculpture, also known as "The Bean."
Bedtime
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4.17360 Chicago Observation Deck (Formerly John Hancock Observatory)
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4.17360 Chicago Observation Deck (Formerly John Hancock Observatory)
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4.39Wrigley Building
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4.39Wrigley Building
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Lakeside Serenity and Navy Pier Excitement
Morning
Enjoy a serene morning at the Lincoln Park & Zoo, followed by a delicious breakfast at Lula Cafe. Afterward, take a walk to the historic Wrigley Field and soak in the atmosphere of this legendary baseball stadium.
Afternoon
Evening
Dine at The Purple Pig, where you can indulge in a variety of cheese, swine, and wine. After dinner, take a relaxing cruise on the Chicago River with the city's lights creating a magical ambiance.
Bedtime
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4.29Lincoln Park & Zoo
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4.29Lincoln Park & Zoo
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4.86Wrigley Field
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4.86Wrigley Field
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Magnificent Mile to Museum Campus
Morning
Start your day with a sumptuous breakfast at Portillo's Hot Dogs, a Chicago classic. Then, take a leisurely walk along the prestigious The Magnificent Mile, known for its upscale shops and boutiques.
Afternoon
For lunch, head to Smoque BBQ and enjoy some of the best barbecue in the city. Afterward, immerse yourself in the wonders of nature at the Shedd Aquarium and explore the diverse marine life.
Evening
Dine at Gibsons Bar & Steakhouse, a Chicago institution, and savor their renowned steaks. Cap off the evening with a visit to the Adler Planetarium, where you can gaze at the stars and learn about the universe.
Bedtime
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4.65The Magnificent Mile
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4.65The Magnificent Mile
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4.75Shedd Aquarium
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4.75Shedd Aquarium
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Cultural Treasures and Architectural Wonders
Morning
Begin with a hearty breakfast at Revolution Brewing, known for its craft beers and pub fare. Then, explore the architectural marvels of the city, starting with the Chicago Cultural Center, home to stunning mosaics and the world's largest Tiffany dome.
Afternoon
Enjoy a lunch at Pequod's Pizza, famous for its deep-dish pies. Afterward, take a guided tour of the Chicago Loop to discover the history and stories behind the city's skyscrapers and landmarks.
Evening
Dine at The Publican, a temple to beer, pork, and oysters. After dinner, take a walk to the historic Chicago Theatre and admire its iconic marquee.
Bedtime
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4.71Chicago Cultural Center
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4.71Chicago Cultural Center
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4.83Chicago Loop
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4.83Chicago Loop
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Parks, Museums, and Culinary Delights
Morning
Enjoy a morning walk in the serene Grant Park, also known as Chicago's "front yard." For breakfast, head to Giordano's for their famous stuffed deep-dish pizza.
Afternoon
Visit the Field Museum and immerse yourself in natural history. For lunch, indulge in the gourmet sandwiches at Eataly Chicago. Afterward, explore the lush greenery and animal exhibits at the Museum of Science and Industry.
Evening
Dine at Girl & the Goat, known for its bold flavors and lively atmosphere. Conclude your Chicago adventure with a visit to the Skydeck Chicago at Willis Tower (Sears Tower), where you can step out onto "The Ledge" and have a heart-stopping view of the city below.
Bedtime
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4.70Grant Park
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4.70Grant Park
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4.56Field Museum
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4.56Field Museum
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