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Ultimate 5-Day Chicago Adventure with Top Attractions and Culinary Delights Itinerary
Last updated: 2024 Jun 14Iconic Chicago Landmarks and River Cruise
Morning
Start your Chicago adventure with a delicious breakfast at Miller's Pub, a historic spot in the heart of the city. Afterward, take a stroll along the Chicago Riverwalk to admire the city's stunning architecture and make your way to the iconic Wrigley Building.
Afternoon
For lunch, enjoy the vibrant atmosphere and eclectic menu at State and Lake Chicago Tavern. Post-lunch, experience the city from a different perspective on the Chicago River 1.5-Hour Guided Architecture Cruise. After the cruise, explore the shops and attractions at Navy Pier.
Evening
Dine at The Gage, known for its upscale, yet rustic, setting and superb cuisine. After dinner, take a leisurely walk to The Magnificent Mile and enjoy the evening lights and the ambiance of this famous shopping district.
Bedtime
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4.72Chicago Riverwalk
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4.72Chicago Riverwalk
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4.39Wrigley Building
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4.39Wrigley Building
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Museum Day and Sky-High Views
Morning
Enjoy a hearty breakfast at Sweetwater Tavern & Grille (Michigan Plaza - Chicago) before heading to the Art Institute of Chicago. Spend the morning exploring the impressive collections at one of the oldest and largest art museums in the country.
Afternoon
For lunch, savor the flavors at LUXBAR, offering a wide range of American classics. Afterward, visit the 360 Chicago Observation Deck (Formerly John Hancock Observatory) and take in breathtaking 360-degree views of the city from 1,000 feet above.
Evening
Indulge in a delightful dinner at The Dearborn, which offers a contemporary take on classic American tavern fare. Cap off the evening with a visit to the lively Rush Street for some after-dinner entertainment and drinks.
Bedtime
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4.61Art Institute of Chicago
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4.61Art Institute of Chicago
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4.17360 Chicago Observation Deck (Formerly John Hancock Observatory)
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4.17360 Chicago Observation Deck (Formerly John Hancock Observatory)
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Cultural Immersion and Evening Delights
Morning
Start your day with breakfast at Burger Bar Chicago, known for its gourmet burgers and extensive beer selection. Afterward, visit the Chicago History Museum to learn about the city's rich history and culture.
Afternoon
Have a leisurely lunch at The Beetle Bar and Grill, a neighborhood spot with a laid-back vibe. Post-lunch, take a walk through the beautiful Lincoln Park & Zoo, one of the oldest zoos in the country, and enjoy the rest of the afternoon in this green oasis.
Evening
For dinner, experience the vibrant atmosphere and delicious Spanish cuisine at Bar Mar by José Andrés. Afterward, take a Gangsters and Ghosts Guided Walking Tour to explore the city's darker history and mysterious hauntings.
Bedtime
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4.77Chicago History Museum
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4.77Chicago History Museum
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4.29Lincoln Park & Zoo
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4.29Lincoln Park & Zoo
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Science, Nature, and Culinary Delights
Morning
Enjoy a delightful breakfast at FireLake Grill House and Cocktail Bar before immersing yourself in the wonders of the natural world at the Field Museum. Spend the morning exploring the museum's extensive collections, including the famous Sue the T. rex.
Afternoon
For lunch, head to Bar Louie - Printers Row for a casual and lively dining experience. Afterward, visit the Shedd Aquarium and be amazed by the diverse aquatic life on display.
Evening
Dine at Bub City, a spot known for its Southern BBQ and live country music. After dinner, take a relaxing Gourmet Brunch, Lunch, or Dinner River Cruise and enjoy the city's skyline from the comfort of a luxurious cruise.
Bedtime
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4.56Field Museum
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4.56Field Museum
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4.75Shedd Aquarium
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4.75Shedd Aquarium
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Farewell to Chicago with Culinary Highlights
Morning
Enjoy a final breakfast at The Green Door Tavern, a historic Chicago speakeasy with a cozy atmosphere. Afterward, take a morning stroll through the serene Grant Park and visit the famous Buckingham Fountain.
Afternoon
For lunch, head to Fadó Irish Pub for some traditional Irish fare and a pint of Guinness. After lunch, spend your afternoon at the interactive and engaging Museum of Science and Industry, exploring the museum's fascinating exhibits.
Evening
Conclude your Chicago journey with a memorable dinner at Bar Siena, offering a modern take on Tuscan cuisine. After dinner, take a Chicago Theatre Tour Experience and learn about the history and behind-the-scenes stories of this iconic venue.
Bedtime
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4.70Grant Park
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4.70Grant Park
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Buckingham Fountain
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Buckingham Fountain
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