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Art, Sights & Culinary Delights: An 8-Day Chicago Experience Itinerary
Last updated: 2024 Jun 14Iconic Chicago Landmarks & Skyline Views
Morning
Start your Chicago adventure with a delightful brunch at Lula Cafe, known for its farm-to-table dishes. Afterward, take a leisurely walk along the iconic The Magnificent Mile, where you can do some shopping and admire the architecture.
Afternoon
For lunch, savor the famous deep-dish pizza at Lou Malnati's Pizzeria. Afterward, visit the John Hancock Center's 360 Chicago Observation Deck for stunning views of the city.
Evening
Enjoy a sophisticated dinner at The Signature Room at the 95th, offering panoramic views of the city. End your day with a relaxing evening walk at Navy Pier.
Bedtime
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4.65The Magnificent Mile
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4.65The Magnificent Mile
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4.17John Hancock Center's 360 Chicago Observation Deck
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4.17John Hancock Center's 360 Chicago Observation Deck
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Artistic Masterpieces & Cultural Immersion
Morning
Indulge in a gourmet breakfast at Alinea, a three-Michelin-starred restaurant. Then, spend the morning exploring the Art Institute of Chicago, home to a world-class collection of art.
Afternoon
For lunch, experience the vibrant flavors of Mexico at Xoco, a top-rated restaurant. Afterward, take a stroll through the historic Chicago Cultural Center.
Evening
Dine at The Publican, known for its communal dining experience and craft beer selection. In the evening, enjoy a performance at the iconic Chicago Theatre.
Bedtime
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4.61Art Institute of Chicago
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4.61Art Institute of Chicago
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4.71Chicago Cultural Center
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4.71Chicago Cultural Center
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Relaxation & Nature in the City
Morning
Start your day with a leisurely breakfast at Little Goat Diner, a cozy spot with a creative menu. Then, spend the morning exploring the green spaces of Grant Park.
Afternoon
For lunch, enjoy a casual meal at Big Star, known for its tacos and outdoor patio. Afterward, visit the Shedd Aquarium to discover the wonders of the underwater world.
Evening
Dine at Gibsons Bar & Steakhouse, a classic Chicago steakhouse. End your day with a relaxing walk along the Chicago Riverwalk.
Bedtime
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4.70Grant Park
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4.70Grant Park
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4.75Shedd Aquarium
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4.75Shedd Aquarium
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Culinary Delights & Neighborhood Exploration
Morning
Enjoy a delicious breakfast at Pequod's Pizza, famous for its caramelized crust. Then, take a food tour to explore the diverse culinary scene of Chicago.
Afternoon
Spend the afternoon visiting the unique neighborhoods of the city, such as Pilsen, Wicker Park, and Logan Square. Stop for a late lunch at a local favorite in one of these areas.
Evening
For dinner, try the innovative dishes at Girl & the Goat, a renowned restaurant. Afterward, explore the vibrant nightlife of Chicago in the neighborhood of your choice.
Bedtime
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Museum Day & Skyline Views
Morning
Start your day with a hearty breakfast at Au Cheval, known for its indulgent burgers. Then, visit the Field Museum of Natural History to learn about the natural world.
Afternoon
For lunch, head to Smoque BBQ for some mouthwatering barbecue. Afterward, take a relaxing cruise on Lake Michigan to enjoy the city's skyline from the water.
Evening
Dine at The Purple Pig, a popular spot for Mediterranean-inspired small plates. End your day with a visit to the Lincoln Park Zoo, which is open late on select days.
Bedtime
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4.56Field Museum of Natural History
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4.56Field Museum of Natural History
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4.29Lincoln Park Zoo
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4.29Lincoln Park Zoo
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Architecture & River Cruise Experience
Morning
Enjoy a leisurely breakfast at Longman & Eagle, a hip spot known for its brunch. Then, take a guided architecture tour to learn about the city's iconic buildings.
Afternoon
For lunch, try the contemporary Italian cuisine at RPM Italian. Afterward, take a relaxing river cruise to admire the city's skyline from a different perspective.
Evening
Dine at Cafe Ba-Ba-Reeba!, a lively restaurant serving Spanish tapas. After dinner, take a stroll along the Chicago Riverwalk.
Bedtime
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4.72Chicago Riverwalk
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4.72Chicago Riverwalk
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Gangsters, Ghosts & Local Flavors
Morning
Start your day with a classic Chicago breakfast at Portillo's Hot Dogs. Then, embark on a guided tour to explore the city's mobster history and haunted locations.
Afternoon
For lunch, enjoy a taste of Chicago at Giordano's, famous for its stuffed deep-dish pizza. Afterward, take a walk through the historic neighborhoods of the city.
Evening
Dine at Frontera Grill, a top-rated Mexican restaurant. In the evening, join a food and ghost tour to experience the city's culinary and supernatural side.
Bedtime
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Farewell to Chicago: Culinary Experiences & Souvenir Shopping
Morning
On your last day in Chicago, enjoy a leisurely breakfast at Eataly Chicago, a vibrant Italian marketplace. Then, spend the morning visiting the city's iconic sights for one last look.
Afternoon
For lunch, savor the flavors of the Mediterranean at The Purple Pig. Afterward, take some time to shop for souvenirs and gifts to remember your Chicago trip.
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