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4-day trip to Chicago Itinerary
Last updated: 2024 Jun 14Exploring the City's Landmarks
Morning
Start your day by taking a 1.5-hour guided architecture cruise along the beautiful Chicago River. Learn about the city's iconic buildings and their history while enjoying the scenic views. After the cruise, grab a delicious brunch at Lula Cafe.
Afternoon
Visit the renowned Art Institute of Chicago and explore its extensive collection of art. Take your time to admire famous masterpieces and discover new artists. For lunch, head to The Purple Pig and indulge in their Mediterranean-inspired dishes.
Evening
Enjoy a leisurely walk along the Chicago Riverwalk and take in the vibrant atmosphere. For dinner, experience the culinary delights of Girl & the Goat, known for its creative and flavorful dishes. End the evening with a drink at The Publican.
Bedtime
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Chicago River
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Art Institute of Chicago
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Chicago Riverwalk
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Chicago's Cultural Side
Morning
Start your day by visiting the Museum of Science and Industry, where you can explore interactive exhibits and learn about various scientific phenomena. For a quick snack, stop by Xoco for some delicious Mexican street food.
Afternoon
Take a guided walking tour of the city's cultural highlights, including the Chicago Cultural Center and the Chicago Theatre. For lunch, try the famous deep-dish pizza at Lou Malnati's Pizzeria.
Evening
Immerse yourself in the vibrant nightlife of Chicago by joining the Chicago Gangsters and Ghosts Guided Walking Tour. Learn about the city's notorious past and visit historic sites. For dinner, savor the flavors of Italian cuisine at Eataly Chicago.
Bedtime
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Museum of Science and Industry
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Chicago Cultural Center
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Chicago Theatre
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Chicago Gangsters and Ghosts Guided Walking Tour
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Sky-high Views and Navy Pier
Morning
Start your day by visiting the iconic Willis Tower Skydeck and The Ledge. Enjoy breathtaking views of the city from the observation deck. For breakfast, grab a bite at Au Cheval, known for its delicious burgers.
Afternoon
Head to Navy Pier and take a ride on the Navy Pier Centennial Wheel. Enjoy panoramic views of Lake Michigan and the city skyline. For lunch, try the famous Chicago-style hot dogs at Portillo's Hot Dogs.
Evening
Embark on a sunset cocktail and architecture tour along the Chicago River. Admire the city's stunning skyline while sipping on your favorite drink. For dinner, indulge in a steak at Gibsons Bar & Steakhouse. End the evening with a visit to Big Star for some drinks and live music.
Bedtime
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Chicago Willis Tower Skydeck and The Ledge Ticket
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Navy Pier
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Chicago Navy Pier Centennial Wheel Regular & Express Ticket
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Museums and Local Delights
Morning
Explore the fascinating exhibits at the Field Museum of Natural History. Learn about dinosaurs, ancient civilizations, and natural history. For breakfast, enjoy a meal at Little Goat Diner.
Afternoon
Take a stroll through the beautiful Millennium Park and admire the famous Cloud Gate sculpture, also known as "The Bean." For lunch, try the mouthwatering barbecue at Smoque BBQ.
Evening
Visit the 360 Chicago Observation Deck and enjoy panoramic views of the city. For dinner, savor the flavors of Chicago-style deep-dish pizza at Giordano's. End your trip with a visit to Revolution Brewing for some local craft beer tasting.
Bedtime
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Field Museum
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Millennium Park
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360 Chicago Observation Deck (Formerly John Hancock Observatory)
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