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7-Day Chicago Exploration with Unique Experiences and Sites Itinerary
Last updated: 2024 Jun 14Iconic Landmarks and River Cruises
Morning
Start your Chicago adventure with a delicious breakfast at Lou Malnati's Pizzeria, known for its famous deep-dish pizza. Afterward, take a stroll along the Chicago Riverwalk to enjoy the morning views of the city's architecture.
Afternoon
Experience the city from the water with the Chicago River 1.5-Hour Guided Architecture Cruise. Afterward, enjoy a classic Chicago-style hot dog for lunch at Portillo's Hot Dogs.
Evening
As the sun sets, head to the 360 Chicago Observation Deck (Formerly John Hancock Observatory) for breathtaking views of the skyline. Cap off the evening with a gourmet dinner at The Signature Room at the 95th, where you can dine with a view.
Bedtime
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4.72Chicago Riverwalk
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4.72Chicago Riverwalk
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4.77Chicago River 1.5-Hour Guided Architecture Cruise
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4.77Chicago River 1.5-Hour Guided Architecture Cruise
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Museums and Sky-high Thrills
Morning
Start your day with a visit to the iconic Willis Tower Skydeck and The Ledge Ticket. Enjoy breakfast with a view at the tower's cafe.
Afternoon
Explore the depths of the ocean at the Shedd Aquarium. For lunch, indulge in some of the best barbecue in the city at Smoque BBQ.
Evening
Take a leisurely walk through Millennium Park, and don't miss the famous "Bean" sculpture. For dinner, savor the flavors of Italy at RPM Italian.
Bedtime
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4.41Willis Tower Skydeck and The Ledge Ticket
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4.41Willis Tower Skydeck and The Ledge Ticket
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4.75Shedd Aquarium
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4.75Shedd Aquarium
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Cultural Wonders and Navy Pier Fun
Morning
Start with a hearty breakfast at The Purple Pig, known for its inventive dishes. Then, immerse yourself in art and history at the Art Institute of Chicago.
Afternoon
Evening
Wind down with a stroll through the elegant The Magnificent Mile, and have a sophisticated dinner at Gibsons Bar & Steakhouse.
Bedtime
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4.61Art Institute of Chicago
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4.61Art Institute of Chicago
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4.48Navy Pier
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4.48Navy Pier
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Historic Tours and Scenic Views
Morning
Start your day with a guided tour of the Tribune Tower, known for its rich history and impressive architecture. Then, enjoy a delightful brunch at Lula Cafe.
Afternoon
Take in the panoramic views of the city from the Chicago 360 Chicago Observation Deck Skip-the-Line Ticket. For lunch, visit Eataly Chicago for a unique Italian dining experience.
Evening
Explore the city's darker history with the Chicago Gangsters and Ghosts Guided Walking Tour. Afterward, enjoy a casual dinner at Xoco, known for its gourmet Mexican street food.
Bedtime
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4.61Tribune Tower
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4.61Tribune Tower
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4.37Chicago 360 Chicago Observation Deck Skip-the-Line Ticket
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4.37Chicago 360 Chicago Observation Deck Skip-the-Line Ticket
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Culinary Delights and Zoo Excursion
Morning
Start with a visit to the Lincoln Park & Zoo, where you can enjoy a morning surrounded by nature and wildlife. For breakfast, indulge in the pastries at Little Goat Diner.
Afternoon
Satisfy your sweet tooth with a visit to the Museum of Ice Cream Entry Ticket. For lunch, enjoy the diverse offerings at Kuma's Corner, known for its burgers with a creative twist.
Evening
Dine at Au Cheval, famous for its award-winning burger, and then take a relaxing evening stroll along the Chicago River to end the day.
Bedtime
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4.29Lincoln Park & Zoo
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4.29Lincoln Park & Zoo
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4.09Museum of Ice Cream Entry Ticket
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4.09Museum of Ice Cream Entry Ticket
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Architectural Marvels and Science Wonders
Morning
Enjoy a delightful breakfast at Cafe Ba-Ba-Reeba!, offering a taste of Spain in Chicago. Then, take a guided tour of the city's architectural gems on the Chicago River Architecture Cruise Skip-the-Ticket-Office.
Afternoon
Explore the interactive and educational exhibits at the Chicago Museum of Science and Industry Ticket. For lunch, visit Girl & the Goat for a memorable dining experience featuring bold flavors and creative dishes.
Evening
Sip on some of the finest wines at Marina City, known for its architectural significance. Enjoy a sophisticated dinner at The Aviary, a culinary experience like no other.
Bedtime
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4.83Chicago River Architecture Cruise Skip-the-Ticket-Office
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4.83Chicago River Architecture Cruise Skip-the-Ticket-Office
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4.61Chicago Museum of Science and Industry Ticket
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4.61Chicago Museum of Science and Industry Ticket
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Hidden Gems and Farewell Views
Morning
Start your final day with a guided tour of the Chicago Underground Pedway & Downtown Secrets Walking Tour. Then, enjoy a delightful breakfast at Longman & Eagle.
Afternoon
Visit the Field Museum of Natural History to explore the world-class exhibits. For lunch, savor the flavors of Spain at Mercat a la Planxa.
Evening
Reflect on your trip with a serene walk through Grant Park, and enjoy a farewell dinner at Moto Restaurant, known for its innovative and artistic approach to cuisine. End your Chicago journey with the Chicago 45- Minute Family-Friendly Architecture River Cruise.
Bedtime
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4.73Chicago Underground Pedway & Downtown Secrets Walking Tour
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4.73Chicago Underground Pedway & Downtown Secrets Walking Tour
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4.68Field Museum of Natural History
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4.68Field Museum of Natural History
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