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Ultimate 5-Day Chicago Exploration with Iconic Landmarks and Culinary Delights Itinerary
Last updated: 2024 Jun 14Iconic Chicago Sights and River Cruise
Morning
Begin your Chicago adventure with breathtaking views from the 360 Chicago Observation Deck (Formerly John Hancock Observatory). Skip the line and enjoy a serene morning with a bird's-eye perspective of the city.
Afternoon
After taking in the skyline, head to the Chicago River 1.5-Hour Guided Architecture Cruise for a narrated tour, learning about the city's famous buildings and their history. Post-cruise, indulge in a classic Chicago lunch at Billy Goat Tavern (Millennium Park).
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360 Chicago Observation Deck (Formerly John Hancock Observatory)
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Chicago River 1.5-Hour Guided Architecture Cruise
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Navy Pier
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Cultural Immersion and Lakefront Serenity
Morning
Immerse yourself in art and culture at the Art Institute of Chicago, home to an impressive collection. Afterward, take a peaceful walk in Millennium Park and capture the iconic "Bean" sculpture.
Afternoon
For lunch, savor the gourmet offerings aboard the Chicago Lake Michigan Gourmet Brunch/Lunch/Dinner Cruise. Enjoy a delectable meal while cruising the waters and taking in the skyline.
Evening
Dine at City Social, where you can enjoy a sophisticated meal with panoramic views of the city. Afterward, take a post-dinner walk at the serene Grant Park and visit the majestic Buckingham Fountain.
Bedtime
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Art Institute of Chicago
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Millennium Park
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Chicago Lake Michigan Gourmet Brunch/Lunch/Dinner Cruise
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Grant Park
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Museum Day and Magnificent Mile
Morning
Start with a visit to the Field Museum, where you can explore natural history and world cultures. Refuel with a delightful breakfast at Doc B's Restaurant (River North).
Afternoon
Post-museum, take a short walk to the Shedd Aquarium, one of the largest indoor aquariums in the world. Afterward, enjoy a shopping spree at the upscale boutiques along The Magnificent Mile and have lunch at LUXBAR.
Evening
As the sun sets, experience the vibrant nightlife of Chicago at The Chicago Theatre on State Street. For dinner, head to Cindy's Rooftop for a memorable dining experience with stunning views of Millennium Park and Lake Michigan.
Bedtime
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Field Museum
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Shedd Aquarium
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The Magnificent Mile
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Chicago Theatre
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Architectural Wonders and Evening Delights
Morning
Explore the unique twin towers of Marina City and then take a walk on the Chicago Riverwalk to admire the city's architecture. Grab a coffee and light breakfast at State and Lake Chicago Tavern to start your day.
Afternoon
Continue your architectural journey with visits to the Wrigley Building and the historic Tribune Tower. For lunch, enjoy the vibrant atmosphere and delicious food at Bar Louie - Printers Row.
Evening
Cap off the day with a visit to the Skydeck Chicago at Willis Tower (Sears Tower) to witness the city from the glass-bottomed ledge. Then, indulge in a sumptuous dinner at The Gage, known for its rustic, yet refined, cuisine.
Bedtime
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Marina City
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Chicago Riverwalk
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Wrigley Building
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Tribune Tower
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Skydeck Chicago at Willis Tower (Sears Tower)
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Parks, Sports, and Evening Entertainment
Morning
Enjoy the morning at Lincoln Park & Zoo, strolling through the lush greenery and visiting the animals. For breakfast, head to Sweetwater Tavern & Grille (Michigan Plaza - Chicago) for a hearty start.
Afternoon
After the park, visit the historic Wrigley Field and take a guided tour to learn about its rich baseball history. For lunch, try the diverse menu at Bar Mar by José Andrés.
Evening
Conclude your trip with a visit to Soldier Field, the iconic home of the Chicago Bears. For a memorable final dinner, dine at The Dearborn, offering a modern take on classic American fare. Afterward, enjoy the vibrant nightlife of the city at your leisure.
Bedtime
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Lincoln Park & Zoo
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Wrigley Field
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Soldier Field
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