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Ultimate 5-Day Chicago Adventure

Ultimate 5-Day Chicago Adventure Itinerary

Last updated: 2024 Jun 14

Discovering Chicago's Iconic Landmarks

Morning
Start your day with a delicious breakfast at Lou Malnati's Pizzeria, known for its famous deep-dish pizza. After breakfast, head to the magnificent Art Institute of Chicago to admire the world-class art collection. Spend the morning exploring the museum's impressive exhibits.
Afternoon
For lunch, enjoy the vibrant atmosphere and Spanish tapas at Cafe Ba-Ba-Reeba!. Afterward, take a leisurely stroll along the beautiful Chicago Riverwalk, where you can enjoy the views of the city's architecture and the Chicago River.
Evening
In the evening, experience the city from a different perspective with a visit to the 360 Chicago Observation Deck (Formerly John Hancock Observatory). Enjoy a drink at the bar and take in the stunning panoramic views of the city. For dinner, indulge in modern Italian cuisine at RPM Italian.
Bedtime
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Art Institute of Chicago

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Chicago Riverwalk

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360 Chicago Observation Deck (Formerly John Hancock Observatory)

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Chicago's Cultural and Culinary Delights

Morning
Start your day with a visit to the Museum of Science and Industry, where you can explore fascinating exhibits and interactive displays. Afterward, enjoy a delightful brunch at Lula Cafe, known for its farm-to-table cuisine.
Afternoon
Spend the afternoon at the iconic Navy Pier, where you can experience the thrill of the Chicago Navy Pier Centennial Wheel Regular & Express Ticket. Afterward, explore the various attractions and shops at the pier.
Evening
For dinner, savor the flavors of Spain at The Purple Pig, known for its Mediterranean-inspired dishes. After dinner, take a leisurely walk along the Chicago River and enjoy the city's beautiful skyline at night.
Bedtime
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Museum of Science and Industry

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Navy Pier

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Chicago Navy Pier Centennial Wheel Regular & Express Ticket

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Chicago River

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Chicago's Architectural Marvels and Culinary Gems

Morning
Start your day with a guided architecture cruise on the Chicago River 1.5-Hour Guided Architecture Cruise. Learn about the city's iconic buildings and history as you cruise along the Chicago River. After the cruise, enjoy a delightful breakfast at Little Goat Diner.
Afternoon
Spend the afternoon exploring the Chicago River Architecture Cruise Skip-the-Ticket-Office and the Chicago Willis Tower Skydeck and The Ledge Ticket. Experience the thrill of stepping out onto the glass ledge and enjoy breathtaking views of the city. For lunch, head to Girl & the Goat for a unique dining experience.
Evening
In the evening, take a guided walking tour of the city's Chicago Gangsters and Ghosts Guided Walking Tour. Explore the city's darker history and hidden secrets. After the tour, enjoy a delicious dinner at Au Cheval, known for its famous cheeseburger.
Bedtime
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Chicago River 1.5-Hour Guided Architecture Cruise

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Chicago Architecture River Cruise Skip-the-Ticket Line

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Chicago Willis Tower Skydeck and The Ledge Ticket

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Chicago Gangsters and Ghosts Guided Walking Tour

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Chicago's Hidden Gems and Culinary Delights

Morning
Start your day with a visit to the Chicago Museum of Ice Cream Entry Ticket, where you can indulge your sweet tooth and enjoy interactive exhibits. Afterward, enjoy a delightful breakfast at Kuma's Corner, known for its gourmet burgers.
Afternoon
Spend the afternoon exploring the city's hidden secrets on the Chicago Underground Pedway & Downtown Secrets Walking Tour. Discover the underground passages and hidden gems of the city. For lunch, head to Big Star for delicious tacos and margaritas.
Evening
In the evening, take a guided walking tour of the city's Chicago Ghosts & Hauntings of the Windy City Walking Tour. Explore the haunted history of Chicago and hear chilling ghost stories. After the tour, enjoy a delightful dinner at Gibsons Bar & Steakhouse.
Bedtime
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Chicago Museum of Ice Cream Entry Ticket

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Chicago Underground Pedway & Downtown Secrets Walking Tour

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Chicago Ghosts & Hauntings of the Windy City Walking Tour

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Chicago's Culinary and Cultural Extravaganza

Morning
Start your day with a visit to the Chicago Field Museum of Natural History Ticket or VIP Tour, where you can explore fascinating exhibits and learn about natural history. Afterward, enjoy a delightful breakfast at Portillo's Hot Dogs.
Afternoon
Spend the afternoon at the The Chicago Theatre Tour Experience, where you can learn about the history of this iconic theater. Afterward, enjoy a delicious lunch at Xoco, known for its Mexican street food.
Evening
In the evening, take a guided walking tour of the city's Chicago Treasures of the Golden Age Walking Tour. Explore the city's golden age and iconic landmarks. After the tour, enjoy a delightful dinner at Smoque BBQ.
Bedtime
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Chicago Field Museum of Natural History Ticket or VIP Tour

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The Chicago Theatre Tour Experience with Licensed Guide

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Chicago Treasures of the Golden Age Walking Tour

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Adjacent Cities

IndianapolisLouisvilleNashvilleMemphisDallasAustinHouston

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