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Ultimate 8-Day Chicago Adventure with Iconic Landmarks and Culinary Delights Itinerary
Last updated: 2024 Jun 14Magnificent Mile and Sky-High Views
Morning
Start your Chicago adventure with a gourmet breakfast at Cindy's Rooftop, offering stunning views of the city. Afterward, take a stroll down the iconic Magnificent Mile, known for its upscale shops and historic architecture.
Afternoon
Enjoy a sumptuous lunch at The Gage, located near Millennium Park. Post-lunch, visit the park to see the famous Cloud Gate (The Bean) and the serene Lurie Garden.
Evening
Dine at LH Rooftop for a sophisticated dinner with panoramic city views. Cap off the evening with a skip-the-line visit to the 360 Chicago Observation Deck to see the city lights from 1,000 feet above.
Bedtime
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4.65Magnificent Mile
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4.65Magnificent Mile
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4.69Cloud Gate (The Bean)
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4.69Cloud Gate (The Bean)
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Cultural Immersion and River Cruising
Morning
Start with a classic Chicago breakfast at Miller's Pub. Then, explore the Art Institute of Chicago, home to a world-class collection, including the famous "American Gothic" painting.
Afternoon
Have a delightful lunch at State and Lake Chicago Tavern before embarking on a Chicago River 1.5-Hour Guided Architecture Cruise, where you'll learn about the city's renowned buildings.
Evening
Experience the vibrant atmosphere of Navy Pier, enjoy the rides, and have dinner at Five Star Bar, a short walk from the pier.
Bedtime
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4.61Art Institute of Chicago
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4.61Art Institute of Chicago
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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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Historic Landmarks and Evening Elegance
Morning
Savor breakfast at Emerald Loop Bar & Grill before visiting the historic Wrigley Building and the nearby Tribune Tower.
Afternoon
Enjoy a hearty lunch at Bub City in the River North area. Post-lunch, take a guided tour of the legendary Chicago Theatre and learn about its rich history.
Evening
Dine at Plymouth Restaurant & Rooftop Bar and then catch a show at the House of Blues, known for its intimate live music performances.
Bedtime
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4.39Wrigley Building
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4.39Wrigley Building
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4.61Tribune Tower
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4.61Tribune Tower
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Science, Nature, and Evening Jazz
Morning
Begin with breakfast at Fadó Irish Pub and then head to the Field Museum to explore natural history and anthropology, including the famous Sue the T. rex.
Afternoon
Have a relaxed lunch at FireLake Grill House and Cocktail Bar in the heart of downtown. Afterward, visit the nearby Shedd Aquarium to witness a diverse range of aquatic life.
Evening
Enjoy a sophisticated dinner at LUXBAR and then unwind with some jazz at Andy's Jazz Club, a Chicago institution for live jazz performances.
Bedtime
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4.56Field Museum
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4.56Field Museum
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4.75Shedd Aquarium
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4.75Shedd Aquarium
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Chinatown Delights and Evening Mysteries
Morning
Start your day with a breakfast at Bar Louie - Printers Row. Then, join a Chicago Taste of Chinatown Food Walking Tour to sample authentic Chinese cuisine and explore the vibrant neighborhood.
Afternoon
After the tour, take a leisurely walk on the Chicago Riverwalk and enjoy the views. For lunch, head to Scofflaw for a unique dining experience.
Evening
Dive into the city's intriguing past with a Chicago Gangsters and Ghosts Guided Walking Tour. Before the tour, grab dinner at Untitled Supper Club, known for its speakeasy vibe and live entertainment.
Bedtime
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4.79Chicago Taste of Chinatown Food Walking Tour
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4.79Chicago Taste of Chinatown Food Walking Tour
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4.72Chicago Riverwalk
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4.72Chicago Riverwalk
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Museum Marvels and Evening Elegance
Morning
Enjoy a breakfast at El Hefe Chicago before immersing yourself in the interactive exhibits of the Chicago Museum of Science and Industry, one of the largest science museums in the world.
Afternoon
Have a leisurely lunch at Elephant & Castle and then visit the 360 Chicago Observation Deck (Formerly John Hancock Observatory) for breathtaking 360-degree views of the city and Lake Michigan.
Evening
Dine at Cindy's Rooftop for a second visit, this time to experience the evening ambiance. Afterward, take a relaxing Chicago Lake Michigan Skyline Cruise to see the city from a different perspective.
Bedtime
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4.31Chicago Museum of Science and Industry
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4.31Chicago Museum of Science and Industry
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4.17360 Chicago Observation Deck (Formerly John Hancock Observatory)
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4.17360 Chicago Observation Deck (Formerly John Hancock Observatory)
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Iconic Parks and Culinary Exploration
Morning
Start with breakfast at House of Blues Restaurant & Bar and then spend the morning at Grant Park, visiting attractions like Buckingham Fountain and the Millennium Monument.
Afternoon
For lunch, head to Bar Siena in the heart of the city. Post-lunch, take a leisurely walk to Millennium Park and enjoy the serene atmosphere and public art, including the famous Cloud Gate.
Evening
Dine at The Gage for a memorable meal, and then take a break from the city buzz with a visit to the Sloomoo Institute, an interactive slime and ASMR experience.
Bedtime
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4.70Grant Park
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4.70Grant Park
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4.69Millennium Park
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4.69Millennium Park
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Sports, Zoos, and Farewell Festivities
Morning
Enjoy a breakfast at LG's Bar & Kitchen before heading to the iconic Wrigley Field for a guided tour, even if you're not a baseball fan, the history and atmosphere are worth it.
Afternoon
Have a delightful lunch at Plymouth Restaurant & Rooftop Bar and then spend a relaxing afternoon at the Lincoln Park Zoo, one of the oldest zoos in the US, or explore the nearby Lincoln Park.
Evening
Conclude your Chicago journey with a farewell dinner at Five Star Bar, reminiscing about your favorite moments. Afterward, take a stroll on the Chicago Riverwalk to soak in the city's evening charm.
Bedtime
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4.86Wrigley Field
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4.86Wrigley Field
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4.29Lincoln Park Zoo
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4.29Lincoln Park Zoo
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