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5-day trip to Chicago Itinerary
Last updated: 2024 Jun 14Exploring the City's Landmarks
Morning
Start your day with a delicious breakfast at Little Goat Diner. Afterward, head to Millennium Park to see the famous The Bean and enjoy the beautiful outdoor art installations. Take a stroll along the Chicago Riverwalk and admire the stunning architecture. Don't miss the iconic Wrigley Building and Tribune Tower.
Afternoon
For lunch, indulge in some mouthwatering deep-dish pizza at Lou Malnati's Pizzeria. Afterward, visit the Art Institute of Chicago to explore its impressive collection of art. Take a walk down the vibrant Magnificent Mile and do some shopping at the various luxury boutiques.
Evening
Enjoy a delicious dinner at The Purple Pig, known for its Mediterranean-inspired dishes. Afterward, catch a show at the historic Chicago Theatre or enjoy a live performance at Blue Chicago, a renowned blues club.
Bedtime
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4.69The Bean
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4.69The Bean
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4.72Chicago Riverwalk
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4.72Chicago Riverwalk
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Chicago River and Skydeck Experience
Morning
Start your day with a relaxing Chicago River 1.5-Hour Guided Architecture Cruise and learn about the city's fascinating architecture. After the cruise, grab a quick bite at Portillo's Hot Dogs for a classic Chicago-style hot dog.
Afternoon
Head to the iconic Willis Tower Skydeck and experience "The Ledge" for breathtaking views of the city. For lunch, enjoy a gourmet meal at Alinea, a three-Michelin-starred restaurant known for its innovative cuisine.
Evening
Take a leisurely walk along Navy Pier and enjoy the stunning views of Lake Michigan. Experience a romantic sunset cruise on the lake with Chicago 1.5-Hour Romantic Sunset Cruise. End the day with a delightful dinner at Girl & the Goat, a popular restaurant offering creative and flavorful dishes.
Bedtime
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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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4.41Willis Tower Skydeck
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4.41Willis Tower Skydeck
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Chicago History and Culture
Morning
Start your day with a fascinating Chicago Mob and Crime Bus Tour to learn about the city's notorious past. Afterward, visit the Field Museum of Natural History to explore its extensive collection of artifacts and exhibits.
Afternoon
Enjoy a delicious lunch at Giordano's and savor their famous stuffed deep-dish pizza. Afterward, take a Chicago Gangsters and Ghosts Walking Tour to discover the hidden stories of Chicago's underworld.
Evening
Experience the vibrant atmosphere of the Chicago Loop and enjoy dinner at The Publican, a trendy restaurant known for its farm-to-table cuisine. Afterward, head to Second City for an evening of laughter at one of the city's most famous comedy clubs.
Bedtime
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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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4.68Field Museum of Natural History
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4.68Field Museum of Natural History
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Cultural and Culinary Delights
Morning
Start your day with a visit to the Museum of Science and Industry, where you can explore interactive exhibits and learn about scientific innovations. Enjoy a delicious brunch at Eataly Chicago, a vibrant Italian marketplace offering a variety of culinary delights.
Afternoon
Take a leisurely stroll through the beautiful Lincoln Park and visit the Lincoln Park Zoo to see a wide range of animals. For lunch, indulge in some mouthwatering barbecue at Smoque BBQ.
Evening
Immerse yourself in the vibrant food scene of Chicago's Chinatown with a Taste of Chinatown Food Walking Tour. Sample delicious Chinese cuisine and learn about the neighborhood's rich history. End the day with a visit to Revolution Brewing for some craft beer and live music.
Bedtime
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4.31Museum of Science and Industry
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4.31Museum of Science and Industry
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4.29Lincoln Park
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4.29Lincoln Park
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City Exploration and Farewell
Morning
Start your day with a scenic bike ride along the Lakefront Trail and enjoy the stunning views of Lake Michigan. Grab a quick breakfast at Xoco for some delicious Mexican-inspired dishes.
Afternoon
Explore the vibrant neighborhood of Wicker Park and visit the unique shops and boutiques. For lunch, head to Big Star for some tasty tacos and refreshing margaritas. Afterward, visit the 360 Chicago Observation Deck for panoramic views of the city.
Evening
Enjoy a farewell dinner at Gibsons Bar & Steakhouse, known for its prime steaks and classic American dishes. End your trip with a relaxing evening at The Violet Hour, a speakeasy-style cocktail lounge known for its creative and expertly crafted drinks.
Bedtime
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4.17360 Chicago Observation Deck
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4.17360 Chicago Observation Deck
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