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Ultimate 5-Day Chicago Adventure with Iconic Landmarks and Culinary Delights Itinerary
Last updated: 2024 Jun 14Magnificent Mile and Sky-High Views
Morning
Start your Chicago adventure with a delightful breakfast at Lula Cafe, known for its cozy atmosphere and farm-to-table dishes. Afterward, take a stroll down the iconic Magnificent Mile, where you can shop at high-end boutiques and admire the historic Wrigley Building .
Afternoon
Enjoy a family-friendly 1.5-hour guided architecture cruise on the Chicago River . After the cruise, satisfy your appetite with a lunch at Big Star, a popular spot for its tacos and outdoor patio.
Evening
Witness the city from new heights at the 360 Chicago Observation Deck with a skip-the-line ticket . As the sun sets, indulge in a dinner at The Purple Pig, offering a menu of cheese, swine, and wine in a lively setting.
Bedtime
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The Magnificent Mile
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Chicago River
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360 Chicago Observation Deck (Formerly John Hancock Observatory)
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Cultural Gems and Waterfront Wonders
Morning
Begin your day with a visit to the world-renowned Art Institute of Chicago with a fast-pass ticket . For breakfast, head to Lou Malnati's Pizzeria for a taste of Chicago's famous deep-dish pizza.
Afternoon
Explore the beautiful Millennium Park and take a selfie at the "Bean" (Cloud Gate). Then, enjoy a gourmet brunch, lunch, or dinner river cruise with stunning views of the city's skyline and architecture.
Evening
After the cruise, take a leisurely walk along the Chicago Riverwalk and end your evening with a delightful meal at Gibsons Bar & Steakhouse, known for its classic American dishes and prime steaks.
Bedtime
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Art Institute of Chicago
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Chicago Riverwalk
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Museum Marvels and Evening Elegance
Morning
Fuel up for a day of exploration with breakfast at Little Goat Diner, a favorite for its creative comfort food. Then, immerse yourself in the wonders of science at the Museum of Science and Industry or opt for a VIP tour at the Field Museum.
Afternoon
For lunch, head to Pequod's Pizza to experience their famous caramelized crust pizza. Spend your afternoon at the Lincoln Park & Zoo, one of the oldest zoos in the country, or visit the historic Wrigley Field for a guided tour.
Evening
Dine at Girl & the Goat, an award-winning restaurant known for its bold flavors and innovative dishes. Afterward, enjoy a live performance at the iconic Chicago Theatre or explore the vibrant nightlife of the city.
Bedtime
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Museum of Science and Industry
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Chicago Field Museum of Natural History Ticket or VIP Tour
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Lincoln Park & Zoo
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Wrigley Field
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Chicago Theatre
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Historic Landmarks and Haunted History
Morning
Start your day with a hearty breakfast at Smoque BBQ, where you can enjoy some of the best barbecue in the city. Then, join the Chicago Gangsters and Ghosts Guided Walking Tour to uncover the darker side of Chicago's history.
Afternoon
After the tour, grab a quick bite at Portillo's Hot Dogs, a Chicago institution known for its classic hot dogs and Italian beef sandwiches. Spend your afternoon at the Navy Pier, where you can enjoy rides, attractions, and stunning views of Lake Michigan.
Evening
For dinner, experience the vibrant atmosphere and delicious cuisine at Xoco, a restaurant by Rick Bayless known for its Mexican street food. End your evening with a thrilling ride on the Centennial Wheel, which offers breathtaking views of the city skyline.
Bedtime
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Culinary Delights and Farewell Views
Morning
Enjoy a leisurely breakfast at Eataly Chicago, an Italian marketplace with a variety of dining options. Then, take a private helicopter tour of the Chicago skyline for a unique and unforgettable perspective of the city.
Afternoon
After the tour, satisfy your lunch cravings at Au Cheval, known for its famous cheeseburger. Spend your afternoon at the Willis Tower Skydeck, where you can step out onto The Ledge for a thrilling experience.
Evening
As the trip comes to an end, reflect on your time in Chicago with a special dinner at Longman & Eagle, a Michelin-starred gastropub known for its innovative menu. Raise a glass to the city at one of the top rooftop bars in Chicago, such as The J. Parker, and enjoy the final views of the skyline.
Bedtime
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Chicago Willis Tower Skydeck and The Ledge Ticket
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