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5-Day Chicago Exploration with Iconic Landmarks and Culinary Delights Itinerary
Last updated: 2024 Jun 14City Icons and Riverfront Marvels
Morning
Start your Chicago adventure with a delightful breakfast at Miller's Pub, a historic gastropub. Afterward, take a serene 1.5-hour Chicago River Guided Architecture Cruise to witness the city's renowned skyline and learn about its iconic buildings.
Afternoon
For lunch, head to Sweetwater Tavern & Grille (Michigan Plaza) for a classic Chicago meal. Spend your afternoon at the vibrant Navy Pier, enjoying its attractions and the stunning views from the Chicago Navy Pier Centennial Wheel with a skip-the-line ticket.
Evening
Dine at Cindy's Rooftop, offering both exquisite cuisine and a panoramic view of the city. After dinner, experience the city lights from the 360 Chicago Observation Deck with a skip-the-line ticket and the added luxury of the Sip and View Ticket.
Bedtime
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4.77Chicago River Guided Architecture Cruise
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4.77Chicago River Guided Architecture Cruise
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4.48Navy Pier
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4.48Navy Pier
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Museum Marvels and Culinary Delights
Morning
Enjoy a scrumptious breakfast at Doc B's Restaurant (River North) before immersing yourself in the scientific wonders of the Museum of Science and Industry with a VIP tour or a regular ticket .
Afternoon
For lunch, savor the flavors at City Social, known for its contemporary American cuisine. Post-lunch, explore the fascinating exhibits at the Field Museum of Natural History with a ticket or VIP tour.
Evening
Indulge in a gourmet dinner cruise on Lake Michigan, enjoying the city's skyline from the water. The cruise offers a perfect blend of sightseeing and a delectable meal.
Bedtime
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4.31Museum of Science and Industry
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4.31Museum of Science and Industry
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4.68Field Museum of Natural History
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4.68Field Museum of Natural History
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Historic Tours and Evening Elegance
Morning
Begin with a breakfast at Elephant & Castle before embarking on the Chicago Gangsters and Ghosts Guided Walking Tour. Explore the city's notorious past and hidden supernatural side.
Afternoon
For lunch, head to FireLake Grill House and Cocktail Bar for a unique dining experience. Spend your afternoon at the 360 Chicago Observation Deck, taking in the breathtaking views and enjoying the thrill of the TILT experience.
Evening
Dine at The Gage, offering a refined setting and an exceptional menu. Afterward, take a leisurely stroll along the Magnificent Mile, enjoying the upscale shops and the evening ambiance of this iconic street.
Bedtime
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4.68Chicago Gangsters and Ghosts Guided Walking Tour
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4.68Chicago Gangsters and Ghosts Guided Walking Tour
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4.37360 Chicago Observation Deck
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4.37360 Chicago Observation Deck
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Artistic Masterpieces and Evening Entertainment
Morning
Start your day with breakfast at Longman & Eagle, known for its creative dishes. Then, skip the line and explore the impressive collection at the Art Institute of Chicago, one of the oldest and largest art museums in the country.
Afternoon
Enjoy a lunch at Roanoke Restaurant, offering a cozy and welcoming atmosphere. Afterward, take a guided Chicago Favorite Foods Walking Tour to taste the diverse culinary scene of the city while learning about its history and culture.
Evening
For dinner, experience the lively atmosphere and delicious food at Billy Goat Tavern (The Original), a Chicago classic. Cap off the night with a thrilling live performance at the Chicago Theatre or enjoy a laid-back evening at Randolph Tavern.
Bedtime
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4.61Art Institute of Chicago
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4.61Art Institute of Chicago
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4.82Chicago Favorite Foods Walking Tour
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4.82Chicago Favorite Foods Walking Tour
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Parks, Zoos, and Culinary Capers
Morning
Enjoy a delightful breakfast at Bar Mar by José Andrés before visiting the Lincoln Park, where you can explore the zoo and the surrounding parkland.
Afternoon
Have a leisurely lunch at Townhouse Restaurant & Wine Bar, known for its elegant ambiance and diverse menu. Spend your afternoon at the Adler Planetarium, exploring the universe and enjoying the skyline from the museum's vantage point.
Evening
Dine at Bar Louie - Printers Row, offering a casual and vibrant setting. After dinner, take a relaxing walk in the Grant Park, also known as Chicago's "front yard," and enjoy the evening breeze.
Bedtime
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4.29Lincoln Park
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4.29Lincoln Park
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4.61Adler Planetarium
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4.61Adler Planetarium
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