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5-Day Chicago Adventure Itinerary
Last updated: 2024 Jun 14Welcome to the Windy City
Morning
Start your Chicago adventure with a visit to Millennium Park. This iconic park is home to the famous Cloud Gate sculpture (The Bean) and offers beautiful gardens and art installations. It's a perfect introduction to the city's vibrant culture.
Afternoon
Head over to Art Institute of Chicago for an afternoon immersed in world-class art. This museum houses an extensive collection of Impressionist and Post-Impressionist paintings. For lunch, enjoy a meal at The Purple Pig, known for its Mediterranean-inspired small plates.
Evening
In the evening, take a leisurely stroll along Chicago Riverwalk. This scenic pathway offers stunning views of the city's architecture and is lined with cafes and bars. For dinner, indulge in some deep-dish pizza at Lou Malnati's Pizzeria.
Bedtime
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4.69Millennium Park
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4.69Millennium Park
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4.61Art Institute of Chicago
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4.61Art Institute of Chicago
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Exploring Chicago's Rich History
Morning
Begin your day with a visit to Skydeck Chicago at Willis Tower (Sears Tower). Enjoy breathtaking views of the city from one of the tallest buildings in the Western Hemisphere. Grab breakfast at Au Cheval, famous for its delicious breakfast options.
Afternoon
Spend your afternoon exploring Field Museum, one of the largest natural history museums in the world. Discover fascinating exhibits on dinosaurs, ancient cultures, and more. For lunch, head to Portillo's Hot Dogs for a taste of classic Chicago-style hot dogs.
Evening
In the evening, catch a show at Chicago Theatre, an iconic venue known for its stunning architecture and top-notch performances. Afterward, dine at Girl & the Goat, renowned for its innovative dishes and vibrant atmosphere.
Bedtime
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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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4.56Field Museum
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4.56Field Museum
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Cultural Gems and Lakeside Views
Morning
Start your day with a visit to Adler Planetarium, where you can explore fascinating exhibits about space and astronomy while enjoying panoramic views of Lake Michigan. Have breakfast at one of Chicago's beloved cafes nearby.
Afternoon
Head over to Shedd Aquarium in the afternoon to discover an incredible variety of marine life from around the world. For lunch, enjoy fresh seafood at Joe's Seafood, Prime Steak & Stone Crab, located nearby.
Evening
Spend your evening at Navy Pier enjoying rides and attractions or simply taking in views of Lake Michigan from this iconic landmark. Dine at Gibsons Bar & Steakhouse for a classic steakhouse experience.
Bedtime
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4.61Adler Planetarium
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4.61Adler Planetarium
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4.75Shedd Aquarium
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4.75Shedd Aquarium
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Architectural Marvels and Local Flavors
Morning
Begin your day with an architectural tour starting with Rookery Building, one of Chicago's most historically significant buildings designed by Frank Lloyd Wright. Have breakfast nearby before continuing your tour.
Afternoon
Explore more architectural wonders by visiting Marina City and taking a walk through The Loop area including stops like The Picasso sculpture. Enjoy lunch at Frontera Grill, known for its delicious Mexican cuisine.
Evening
End your day with some live music at House of Blues. Savor dinner while enjoying soulful performances in this iconic venue.
Bedtime
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4.73Rookery Building
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4.73Rookery Building
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4.84Marina City
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4.84Marina City
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Final Day of Lakeside Serenity
Morning
Start your final day in Chicago with a visit to Lincoln Park & Zoo. This historic zoo is one of the oldest in the country and offers free admission. Enjoy a morning coffee at a nearby café while taking in the beautiful surroundings of Lincoln Park.
Afternoon
Spend your afternoon exploring Museum of Science and Industry. This massive museum features interactive exhibits on everything from space exploration to genetics. For lunch, head to Smoque BBQ for some mouthwatering barbecue.
Evening
End your Chicago adventure with a visit to 360 Chicago Observation Deck (Formerly John Hancock Observatory). Enjoy stunning views of the city skyline and Lake Michigan as the sun sets. For dinner, indulge in a memorable meal at Alinea, one of Chicago's most acclaimed restaurants.
Bedtime
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4.29Lincoln Park & Zoo
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4.29Lincoln Park & Zoo
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4.31Museum of Science and Industry
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4.31Museum of Science and Industry
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