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Chicago Adventure - 5 Days of Fun

Chicago Adventure - 5 Days of Fun Itinerary

Last updated: 2024 Jun 14

Welcome to the Windy City

Morning
From O’Hare Airport to Chicago Private Sedan Transfer - Start your trip with a smooth and comfortable transfer from O'Hare International Airport to your hotel in downtown Chicago. This private sedan transfer ensures you begin your journey stress-free.
Afternoon
Millennium Park - Explore one of Chicago's most iconic landmarks. Walk around the beautiful gardens, admire the Cloud Gate sculpture (also known as 'The Bean'), and enjoy the Crown Fountain.
Evening
Alinea - End your first day with an unforgettable dining experience at Alinea, one of Chicago's most celebrated restaurants. Indulge in a multi-course tasting menu that will delight your senses.
Bedtime
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Cultural Gems and Culinary Delights

Morning
Art Institute of Chicago - Spend your morning exploring this world-renowned art museum. Marvel at masterpieces from various periods and cultures, including works by Monet, Van Gogh, and Picasso.
Afternoon
Girl & The Goat - Enjoy a delightful lunch at Girl & The Goat, known for its innovative dishes and vibrant atmosphere. Don't miss their famous goat empanadas!
Evening
Chicago Theatre - Catch a show or simply take a guided tour of this historic theatre. Its stunning architecture and rich history make it a must-visit.
Bedtime
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Sky-high Views and Lakeside Fun

Morning
Skydeck Chicago at Willis Tower (Sears Tower) - Start your day with breathtaking views from the Skydeck at Willis Tower. Step out onto 'The Ledge' for an exhilarating experience high above the city.
Afternoon
Portillo's Hot Dogs - Grab a classic Chicago-style hot dog for lunch at Portillo's Hot Dogs. It's a local favorite that you won't want to miss.
Evening
Navy Pier - Spend your evening enjoying the attractions at Navy Pier. From rides to restaurants to live entertainment, there's something for everyone.
Bedtime
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Exploring Chicago's Historic and Modern Marvels

Morning
Chicago Riverwalk - Start your day with a leisurely stroll along the Chicago Riverwalk. Enjoy the scenic views of the city’s architecture and the vibrant atmosphere along the river.
Afternoon
Field Museum - Spend your afternoon exploring one of the largest natural history museums in the world. Discover fascinating exhibits, including Sue, the largest and most complete T. rex ever found.
Evening
The Purple Pig - End your day with a delightful dinner at The Purple Pig. Known for its Mediterranean-inspired small plates, this restaurant offers a unique dining experience in a lively setting.
Bedtime
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