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Ultimate 5-Day Chicago Adventure with Iconic Landmarks and Culinary Delights Itinerary
Last updated: 2024 Jun 14Iconic Chicago Landmarks and River Cruises
Morning
Begin your Chicago adventure with a skip-the-line visit to the 360 Chicago Observation Deck, where you'll enjoy breathtaking panoramic views of the city and Lake Michigan. After taking in the skyline, head to Sweetwater Tavern & Grille (Michigan Plaza) for a hearty breakfast to fuel your day.
Afternoon
Experience the city's renowned architecture on a Chicago River 1.5-Hour Guided Architecture Cruise. Learn about the history and design of Chicago's famous buildings as you cruise along the Chicago River. For lunch, enjoy a classic Chicago-style hot dog at Five Star Bar, a local favorite.
Evening
Stroll along the Chicago Riverwalk as the sun sets, then indulge in a delicious dinner at Gilt Bar, known for its cozy atmosphere and innovative cuisine. End the evening with a visit to the historic Chicago Theatre for a memorable live performance.
Bedtime
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Chicago 360 Chicago Observation Deck General Admission
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Chicago River 1.5-Hour Guided Architecture Cruise
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Chicago Riverwalk
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Chicago Theatre
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Art, Culture, and Museum Marvels
Morning
Start your day with a fast-pass entry to the world-renowned Art Institute of Chicago. Explore the impressive collection of art and spend your morning immersed in creativity. For breakfast, enjoy the ambiance and a cup of coffee at Cindy's Rooftop with its stunning views of Millennium Park.
Afternoon
After the museum, take a leisurely walk to Millennium Park to see the iconic "Bean" sculpture and enjoy the park's architecture. For lunch, head to The Gage, located just steps away from the park, and savor their upscale pub fare.
Evening
As the day winds down, experience the vibrant atmosphere of The Magnificent Mile, Chicago's premier shopping destination. For dinner, indulge in the gourmet burgers at Burger Bar Chicago, and then take an evening stroll to enjoy the city lights and the grandeur of the Wrigley Building and Tribune Tower.
Bedtime
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Art Institute of Chicago
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Millennium Park
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The Magnificent Mile
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Family-Friendly Fun and Museum Marvels
Morning
Enjoy a family-friendly morning with a visit to the Chicago Children's Museum at Navy Pier. Let the kids explore the interactive exhibits while you grab a quick breakfast at Bub City, known for its Southern BBQ and lively atmosphere.
Afternoon
Spend the afternoon at the Shedd Aquarium and the Field Museum, both located in the Museum Campus. Take a break for lunch at Plymouth Restaurant & Rooftop Bar, where you can enjoy a meal with a view of the city skyline.
Evening
After the museums, take a relaxing walk in Grant Park, also known as "Chicago's front yard." For dinner, head to The Dearborn for a taste of contemporary American cuisine in a sophisticated setting.
Bedtime
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Shedd Aquarium
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Shedd Aquarium
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Field Museum
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Grant Park
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Chicago's Culinary Scene and Prohibition History
Morning
Start your day with a guided walking tour of Chicago's Favorite Foods. Sample a variety of Chicago's culinary delights, from deep-dish pizza to gourmet donuts. The tour will take you through the city's neighborhoods, providing a unique way to experience Chicago's food culture.
Afternoon
After the tour, explore the city at your own pace with a hop-on hop-off sightseeing tour on the Chicago Big Bus. Grab lunch at one of the stops, perhaps at LUXBAR, known for its classic American dishes and extensive drink menu.
Evening
Dive into Chicago's history with a Prohibition Speakeasies Bus Tour or Walking Tour. Learn about the city's notorious past and visit hidden bars and speakeasies. For dinner, enjoy the vibrant atmosphere and delicious Mexican cuisine at Bar Siena.
Bedtime
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Chicago Classic Food Walking Tour with Bike or Kayak Rental
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Sky-high Thrills and Cultural Delights
Morning
Rise early for a VIP experience at the Willis Tower Skydeck, where you can enjoy the breathtaking views of the city without the crowds. Afterward, grab breakfast at Miller's Pub, a Chicago institution known for its comfort food and extensive beer selection.
Afternoon
Spend your afternoon exploring the vibrant neighborhood of Wrigleyville, home to the historic Wrigley Field. Enjoy lunch at Fadó Irish Pub, where you can savor traditional Irish dishes and a pint of Guinness.
Evening
Conclude your Chicago journey with a visit to the Lincoln Park Zoo, one of the oldest zoos in the country. Afterward, enjoy a farewell dinner at 676 Restaurant & Bar, located in the Omni Chicago Hotel, offering a sophisticated dining experience with a modern American menu.
Bedtime
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Skydeck Chicago at Willis Tower (Sears Tower)
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