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Ultimate 7-Day Chicago to Milan and Beyond Itinerary Itinerary
Last updated: 2024 Jun 14Iconic Chicago Landmarks and River Cruises
Morning
Start your Chicago adventure with a delicious breakfast at Lou Malnati's Pizzeria, known for its famous deep-dish pizza. Afterward, take a stroll along the Chicago Riverwalk to admire the city's architecture and then head to the Chicago River for a morning guided architecture cruise with coffee onboard.
Afternoon
For lunch, enjoy the vibrant atmosphere and tacos at Big Star in Wicker Park. Afterward, visit the iconic Wrigley Building and explore the shops and boutiques along The Magnificent Mile.
Evening
Dine with a view at The Signature Room at the 95th, offering stunning panoramic views of the city. End your day by experiencing the breathtaking sights from the 360 Chicago Observation Deck with a sip and view ticket.
Bedtime
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4.72Chicago Riverwalk
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4.72Chicago Riverwalk
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4.61Chicago River
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4.61Chicago River
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Museum Day and Lake Michigan Cruise
Morning
Enjoy a morning coffee and pastry at Lula Cafe in Logan Square before heading to the Field Museum. Explore the natural history exhibits and consider joining the VIP tour for an in-depth experience.
Afternoon
Have a leisurely lunch at Smoque BBQ, known for its mouthwatering barbecue. Spend your afternoon at Navy Pier, and then take a Lake Michigan buffet brunch, lunch, or dinner cruise to enjoy the skyline from the water.
Evening
For dinner, savor the flavors of Italy at Eataly Chicago, a vibrant marketplace with various dining options. Cap off the evening with a walk through the Millennium Park to see the famous "Bean" (Cloud Gate) sculpture.
Bedtime
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4.56Field Museum
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4.56Field Museum
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4.48Navy Pier
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4.48Navy Pier
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Cultural Chicago and Evening Delights
Morning
Start your day with a breakfast at Little Goat Diner, offering a menu of creative comfort food. Then, immerse yourself in art at the Art Institute of Chicago with a fast-pass ticket, allowing you to explore the world-renowned collections with ease.
Afternoon
Enjoy a light lunch at Xoco, known for its gourmet Mexican street food. Afterward, take a guided walking tour of the city's downtown secrets, including the Chicago Pedway.
Evening
Dine at Girl & the Goat, an award-winning restaurant serving bold flavors in a lively setting. After dinner, take part in a Chicago Prohibition Speakeasies Bus Tour or Walking Tour to learn about the city's history of bootlegging and speakeasies.
Bedtime
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4.61Art Institute of Chicago
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4.61Art Institute of Chicago
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4.73Chicago Pedway
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4.73Chicago Pedway
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Culinary Exploration and Evening Breezes
Morning
Wake up with a coffee and pastry at RPM Italian, known for its modern Italian cuisine. Then, take a Chicago Favorite Foods Guided Walking Tour to sample a variety of Chicago's classic dishes.
Afternoon
Enjoy a hearty lunch at Giordano's, famous for its stuffed deep-dish pizza. Spend your afternoon at the serene Lincoln Park Zoo, and then stroll through the lush Lincoln Park.
Evening
For dinner, head to Gibsons Bar & Steakhouse for a classic Chicago steak experience. End your day with a relaxing walk along the Lakefront Trail, taking in the cool lake breeze.
Bedtime
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4.82Chicago Favorite Foods Guided Walking Tour
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4.82Chicago Favorite Foods Guided Walking Tour
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4.29Lincoln Park Zoo
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4.29Lincoln Park Zoo
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Marvelous Milan's Must-See Sights
Morning
Begin your Italian journey with a delightful breakfast at Recommended Restaurant before visiting the historic Milan Cathedral (Duomo). Climb to the rooftop for a stunning view of the city.
Afternoon
Enjoy a sumptuous lunch at Recommended Restaurant and then explore the grandeur of the Galleria Vittorio Emanuele II, one of the world's oldest shopping malls.
Evening
Dine at Recommended Restaurant and take a leisurely walk through the charming streets of Brera District (Via Brera), known for its artistic and bohemian atmosphere.
Bedtime
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4.59Galleria Vittorio Emanuele II
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4.59Galleria Vittorio Emanuele II
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4.19Brera District (Via Brera)
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4.19Brera District (Via Brera)
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Bologna's Rich History and Gastronomic Delights
Morning
Start your day with a traditional Bolognese breakfast at Recommended Restaurant. Then, take a guided walking tour of the city, visiting landmarks such as the Asinelli Tower (Torre degli Asinelli) and the Fountain of Neptune (Fontana del Nettuno).
Afternoon
Indulge in a savory lunch at Recommended Restaurant, and then explore the rich culinary history of Bologna at the Museum of the History of Bologna (Museo della Storia di Bologna).
Evening
Savor a traditional Bolognese dinner at Recommended Restaurant, and conclude your day with a relaxing passeggiata (evening stroll) through the charming streets of Bologna Old Town (Quadrilatero).
Bedtime
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4.54Asinelli Tower (Torre degli Asinelli)
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4.54Asinelli Tower (Torre degli Asinelli)
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4.65Bologna Old Town (Quadrilatero)
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4.65Bologna Old Town (Quadrilatero)
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Venice's Enchanting Canals and Cultural Wonders
Morning
Begin your day with a delightful breakfast at Recommended Restaurant, then take a gondola ride through the picturesque canals of Venice.
Afternoon
Enjoy a leisurely lunch at Recommended Restaurant, and then explore the rich cultural heritage of the city at the Doge's Palace (Palazzo Ducale) and St. Mark's Basilica (Basilica di San Marco).
Evening
Dine at Recommended Restaurant and watch the sunset over the lagoon. Take a romantic evening stroll and get lost in the labyrinth of narrow streets and hidden piazzas.
Bedtime
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4.36Venice
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4.36Venice
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4.65St. Mark's Basilica (Basilica di San Marco)
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4.65St. Mark's Basilica (Basilica di San Marco)
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