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Ultimate 5-Day Chicago Exploration with Top Attractions and Dining Itinerary
Last updated: 2024 Jun 14Iconic Landmarks and River Cruises
Morning
Begin your Chicago adventure with a classic deep-dish pizza breakfast at Lou Malnati's Pizzeria. After fueling up, take a stroll along the Chicago Riverwalk to admire the city's architecture and make your way to the departure point for the Chicago River 1.5-Hour Guided Architecture Cruise. Learn about the famous buildings and their history as you glide along the river.
Afternoon
For lunch, enjoy the Chicago-style hot dogs at Portillo's Hot Dogs. Post lunch, visit the iconic Navy Pier for a fun-filled afternoon. Take a ride on the Ferris wheel and explore the various attractions and shops on the pier. You can also opt for the Chicago 45-Minute Family-Friendly Architecture River Cruise for a shorter, more kid-friendly architectural experience.
Evening
As the sun sets, head to 360 Chicago Observation Deck (Formerly John Hancock Observatory) with your skip-the-line ticket to witness breathtaking 360-degree views of the city. For dinner, indulge in Mediterranean-inspired dishes at The Purple Pig, known for its vibrant flavors and lively atmosphere.
Bedtime
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4.72Chicago Riverwalk
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4.72Chicago Riverwalk
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4.77Chicago River 1.5-Hour Guided Architecture Cruise
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4.77Chicago River 1.5-Hour Guided Architecture Cruise
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Museum Marvels and Scenic Views
Morning
Kick off your day with a hearty breakfast at Gino's East, famous for its deep-dish pizza. After breakfast, make your way to the Art Institute of Chicago with your fast-pass ticket. Spend the morning exploring the impressive art collections, including the iconic "American Gothic."
Afternoon
For lunch, savor the flavors of Mexico at Xoco, offering a menu of traditional street foods. Post lunch, visit the Millennium Park to see the famous "Bean" at the Cloud Gate. Take a leisurely walk in the park and enjoy the outdoor art installations.
Evening
As the evening sets in, enjoy a sophisticated dining experience at Spiaggia, offering panoramic views of Lake Michigan. After dinner, take a stroll on the Magnificent Mile and explore the upscale boutiques and shops.
Bedtime
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4.61Art Institute of Chicago
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4.61Art Institute of Chicago
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4.69Millennium Park
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4.69Millennium Park
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Gastronomic Delights and Historic Tours
Morning
Start your day with a delightful breakfast at Cafe Ba-Ba-Reeba!, known for its Spanish tapas and lively ambiance. Post breakfast, embark on the Chicago Taste of Chinatown Food Walking Tour to explore the vibrant Chinatown neighborhood and savor its culinary offerings.
Afternoon
For lunch, head to Big Star for some mouthwatering tacos and a selection of over 200 tequilas. After lunch, take the Chicago Mob and Crime Bus Tour to delve into the city's notorious past and visit the historic crime scenes.
Evening
Dine at Girl & the Goat, an award-winning restaurant known for its bold flavors and innovative dishes. After dinner, join the Chicago Gangsters and Ghosts Guided Walking Tour to uncover the hidden history and paranormal side of Chicago.
Bedtime
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4.79Chicago Taste of Chinatown Food Walking Tour
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4.79Chicago Taste of Chinatown Food 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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Science, History, and Speakeasies
Morning
Enjoy a leisurely breakfast at Honey Butter Fried Chicken, where you can indulge in their signature fried chicken sandwiches. After breakfast, visit the Field Museum or opt for the VIP tour to gain exclusive access to some of the museum's renowned collections.
Afternoon
For lunch, visit The Publican, a European beer hall-inspired restaurant serving hearty, rustic dishes. Post lunch, explore the Adler Planetarium and immerse yourself in the world of astronomy and astrophysics.
Evening
Dine at Parachute, a Michelin-starred restaurant offering a unique blend of Korean and American flavors. After dinner, choose between a Chicago Prohibition Speakeasies Bus Tour or Walking Tour to experience the hidden bars and learn about the city's prohibition history.
Bedtime
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4.56Field Museum
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4.56Field Museum
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4.61Adler Planetarium
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4.61Adler Planetarium
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Leisurely Strolls and Culinary Capers
Morning
Start your final day with breakfast at Lula Cafe, a neighborhood favorite known for its seasonal and locally sourced menu. After breakfast, take a leisurely walk in the Lincoln Park & Zoo and enjoy the lush greenery and the diverse range of animals.
Afternoon
For lunch, head to Fat Rice to experience the unique flavors of Macanese cuisine. Post lunch, visit the Skydeck Chicago at Willis Tower (Sears Tower) with your skip-the-line ticket and step out onto The Ledge for an exhilarating experience.
Evening
Conclude your Chicago journey with a grand dinner at Alinea, a three-Michelin-star restaurant known for its avant-garde culinary creations and immersive dining experience. After dinner, you can opt for a Chicago Museum of Illusions Timed Entrance Ticket to enjoy an interactive and mind-bending experience.
Bedtime
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4.29Lincoln Park & Zoo
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4.29Lincoln Park & Zoo
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4.27Skydeck Chicago at Willis Tower (Sears Tower)
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4.27Skydeck Chicago at Willis Tower (Sears Tower)
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