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Ultimate 5-Day Chicago Exploration with Top Attractions and Dining Itinerary
Last updated: 2024 Jun 14Iconic Landmarks and Sky-High Views
Morning
Start your Chicago adventure with a delicious breakfast at Lou Malnati's Pizzeria, known for its deep-dish pizza. After fueling up, head to the Chicago Riverwalk for a morning stroll, taking in the city's stunning architecture.
Afternoon
For lunch, enjoy the vibrant atmosphere and tacos at Big Star in Wicker Park. Post-lunch, visit the Wrigley Building and then take the Chicago River 1.5-Hour Guided Architecture Cruise to learn about the city's famous buildings.
Evening
Dine at The Signature Room at the 95th for dinner with a view. Afterward, experience the thrill of standing on Skydeck Chicago at Willis Tower (Sears Tower)'s Ledge, offering breathtaking views of the city at night.
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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Cultural Immersion and Navy Pier Fun
Morning
Enjoy a classic Chicago breakfast at Au Cheval, famous for its burgers. Then, spend your morning exploring the Art Institute of Chicago, home to a world-class collection of art spanning centuries.
Afternoon
Have a delightful lunch at The Purple Pig, offering a unique Mediterranean menu. Afterward, take a leisurely walk to Navy Pier and experience the Chicago Navy Pier Centennial Wheel Regular & Express Ticket for panoramic views of the city and Lake Michigan.
Evening
For dinner, savor the flavors of Italy at RPM Italian. Cap off the evening with a Chicago River Guided Sunset Cocktail & Architecture Tour, combining drinks, bites, and beautiful views.
Bedtime
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4.61Art Institute of Chicago
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4.61Art Institute of Chicago
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4.48Navy Pier
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4.48Navy Pier
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Museum Marvels and Evening Delights
Morning
Start your day with breakfast at Little Goat Diner, offering a modern take on classic diner fare. Then, head to the Field Museum for a morning of exploring natural history and cultural exhibits.
Afternoon
Enjoy a lunch at Girl & The Goat, known for its bold flavors and innovative dishes. Post-lunch, visit the 360 Chicago Observation Deck (Formerly John Hancock Observatory) with your 360 Chicago Observation Deck Sip and View Ticket for a relaxed afternoon admiring the city from above.
Evening
Dine at The Publican, a European-inspired beer hall with an extensive menu. Conclude your day with a visit to the historic The Chicago Theatre for a guided tour experience.
Bedtime
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4.56Field Museum
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4.56Field Museum
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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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Gangsters, Ghosts, and Gourmet Eats
Morning
Have breakfast at Kuma's Corner, a rock 'n' roll burger bar. Then, join the Chicago Gangsters and Ghosts Guided Walking Tour to uncover the city's darker history and infamous past.
Afternoon
Enjoy a lunch at Smoque BBQ, where you can indulge in some of the best barbecue in the city. Afterward, take the Chicago Mob and Crime Bus Tour to explore the locations where Chicago's most notorious crimes took place.
Evening
For dinner, experience the unique menu at Alinea, one of the world's best restaurants. Afterward, if you're up for it, join the Chicago Gangsters and Food Tasting Walking Tour to combine history with delicious food samples.
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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4.39Chicago Mob and Crime Bus Tour
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4.39Chicago Mob and Crime Bus Tour
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Parks, Zoos, and Farewell Views
Morning
Start your final day with breakfast at Portillo's Hot Dogs, a Chicago institution. Then, spend your morning at Lincoln Park & Zoo, enjoying the beautiful greenery and a wide variety of animals.
Afternoon
Have a relaxed lunch at Xoco, offering a modern take on Mexican street food. Afterward, visit the 360 Chicago Observation Deck (Formerly John Hancock Observatory) for a second visit, this time during the day with your Chicago 360 Chicago Observation Deck Skip-the-Line Ticket.
Evening
Dine at Eataly Chicago, an Italian marketplace with multiple dining options. End your trip with a serene Chicago Lake Michigan Skyline Cruise, reflecting on your Chicago journey with the city's skyline as your backdrop.
Bedtime
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4.29Lincoln Park & Zoo
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4.29Lincoln Park & Zoo
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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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