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Ultimate 5-Day Chicago Adventure Itinerary
Last updated: 2024 Jun 14Iconic Chicago Landmarks
Morning
Start your day with a delicious breakfast at Lou Malnati's Pizzeria, famous for its deep-dish pizza. Afterward, embark on the Chicago River 1.5-Hour Guided Architecture Cruise to admire the city's stunning skyline and learn about its architectural history.
Afternoon
For lunch, head to Giordano's for their renowned stuffed pizza. Then, visit the 360 Chicago Observation Deck Skip-the-Line Ticket at the John Hancock Center to enjoy panoramic views of the city and Lake Michigan.
Evening
Enjoy a delightful dinner at The Signature Room at the 95th, offering breathtaking views of the city. Afterward, take a leisurely stroll along the Chicago Riverwalk to experience the city's vibrant nightlife.
Bedtime
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Chicago River 1.5-Hour Guided Architecture Cruise
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Chicago 360 Chicago Observation Deck General Admission
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Chicago Riverwalk
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Cultural Immersion and Culinary Delights
Morning
Start your day with a gourmet brunch cruise on the Chicago Gourmet Brunch, Lunch, or Dinner River Cruise. Indulge in a delightful meal while cruising along the Chicago River and enjoying the city's iconic landmarks.
Afternoon
After the cruise, explore the Art Institute of Chicago, home to an impressive collection of art from around the world. For lunch, head to The Purple Pig for their renowned Mediterranean-inspired dishes.
Evening
For a unique dining experience, visit Au Cheval and savor their famous cheeseburger. Afterward, take a guided Chicago Gangsters and Ghosts Guided Walking Tour to learn about the city's dark and mysterious past.
Bedtime
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Chicago Gourmet Brunch, Lunch, or Dinner River Cruise
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Art Institute of Chicago
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Chicago Gangsters and Ghosts Guided Walking Tour
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Museums and Culinary Adventures
Morning
Start your day with a visit to the Museum of Science and Industry Ticket, where you can explore interactive exhibits and learn about scientific innovations. For breakfast, head to Lula Cafe for their creative and locally-sourced dishes.
Afternoon
After the museum, enjoy a delicious lunch at Little Goat Diner, known for its innovative comfort food. Then, visit the Field Museum of Natural History Ticket or VIP Tour to discover the world of natural history and anthropology.
Evening
For dinner, experience the vibrant atmosphere of Big Star, known for its tacos and margaritas. Afterward, take a stroll through the Millennium Park and admire the iconic Cloud Gate sculpture, also known as "The Bean."
Bedtime
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Chicago Griffin Museum of Science and Industry Ticket
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Chicago Field Museum of Natural History Ticket or VIP Tour
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Millennium Park
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Culinary Delights and Sky-High Views
Morning
Start your day with a hearty breakfast at Kuma's Corner, famous for its heavy metal-themed burgers. Afterward, visit the Chicago Willis Tower Skydeck and The Ledge Ticket to step out onto the glass-floored balconies and enjoy breathtaking views of the city.
Afternoon
For lunch, head to Smoque BBQ for their mouthwatering barbecue specialties. Then, explore the Navy Pier, where you can enjoy rides, attractions, and stunning views of Lake Michigan.
Evening
Enjoy a delightful dinner at Girl & the Goat, known for its bold and innovative flavors. Afterward, visit the Chicago 360 Chicago Observation Deck Sip and View Ticket at the John Hancock Center for a memorable evening with panoramic views and signature cocktails.
Bedtime
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Chicago Willis Tower Skydeck and The Ledge Ticket
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Navy Pier
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Chicago 360 Chicago Observation Deck Sip and View Ticket
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Culinary Exploration and Farewell to Chicago
Morning
Start your day with a visit to the Adler Planetarium, where you can explore the universe and learn about space science. For breakfast, head to Portillo's Hot Dogs for a classic Chicago-style hot dog.
Afternoon
After the planetarium, enjoy a delicious lunch at Xoco, known for its Mexican street food-inspired dishes. Then, take a Chicago Hop-on Hop-off Sightseeing Tour by Open-top Bus to explore the city's diverse neighborhoods and attractions.
Evening
For your final dinner in Chicago, visit Gibsons Bar & Steakhouse for a classic steakhouse experience. Afterward, take a stroll along The Magnificent Mile and indulge in some last-minute shopping before bidding farewell to the Windy City.
Bedtime
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Adler Planetarium
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Chicago Hop-on Hop-off Sightseeing Tour by Open-top Bus
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The Magnificent Mile
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