Ultimate 7-Day Chicago to Milan and Italian Cities Adventure Itinerary

Start with a hearty breakfast at The Purple Pig, offering a menu of cheese, swine, and wine. Then, spend your morning at the Field Museum, exploring natural history and the world's cultures.

Enjoy a quick bite at Xoco, known for its gourmet Mexican street food, before immersing yourself in the wonders of the Shedd Aquarium.

Dine at Girl & the Goat, an award-winning restaurant serving high-quality, bold dishes. Finish your day with a leisurely walk at Navy Pier, Chicago's iconic lakefront destination.

Start your day with a delicious breakfast at Eataly Chicago, a vibrant Italian marketplace. Then, immerse yourself in art at the Art Institute of Chicago with a Fast-Pass Ticket.

Have lunch at Little Goat Diner, a cozy spot with a menu of comfort food. Then, take a walk in the beautiful Millennium Park and visit the famous Cloud Gate (The Bean).

Enjoy a sophisticated dinner at RPM Italian, known for its sleek and modern ambiance. Cap off your evening with a visit to the Skydeck Chicago at Willis Tower (Sears Tower) and experience "The Ledge" for heart-stopping views of the city.

Begin your day with a traditional Italian breakfast at a local cafe. Then, immerse yourself in the heart of Milan's fashion district, visiting the elegant Galleria Vittorio Emanuele II and the famous La Scala Opera.

Enjoy a sumptuous lunch at {Ristorante Galleria} within the Galleria Vittorio Emanuele II, savoring classic Milanese dishes. Spend your afternoon exploring the historic Sforza Castle (Castello Sforzesco) and its surrounding gardens.

For dinner, experience the innovative flavors of Da Vittorio, a Michelin-starred restaurant known for its exquisite cuisine. Conclude your day with a leisurely walk through the vibrant Brera district, known for its art galleries and charming streets.

Start your day with a traditional Bolognese breakfast at a local cafe. Then, take a guided walking tour of the city, visiting the iconic Two Towers (Due Torri) and exploring the historic streets of the medieval center.

Enjoy a leisurely lunch at Trattoria Anna Maria, a beloved restaurant serving authentic Bolognese cuisine. Spend your afternoon visiting the renowned Basilica of San Petronio (Basilica di San Petronio) and the fascinating Archiginnasio of Bologna (Archiginnasio di Bologna), the ancient seat of the University of Bologna.

For dinner, indulge in the rich flavors of regional cuisine at Osteria dell'Orsa, a popular spot among locals and visitors alike. Afterward, take a leisurely passeggiata (evening stroll) through the charming streets of Bologna, known for its vibrant atmosphere and lively piazzas.

Fuel up for an exciting day with a hearty breakfast at your hotel or a local cafe. Then, make your way to the Autodromo Enzo e Dino Ferrari to witness the adrenaline-pumping action of the Imola F1 race.

Enjoy a satisfying lunch at one of the trackside restaurants, taking in the vibrant atmosphere and discussing the morning's race. Afterward, explore the historic town of Imola, visiting its charming piazzas and the majestic Rocca Sforzesca (Sforza Castle).

For dinner, savor the flavors of Emilian cuisine at Ristorante San Domenico, a Michelin-starred restaurant known for its exquisite dishes and elegant ambiance. Reflect on the day's excitement as you enjoy a post-dinner digestivo (digestif) and prepare for the journey to Venice tomorrow.

Begin your day with a traditional Venetian breakfast at a local cafe. Then, take a gondola ride through the enchanting canals of Venice Canals (Gondolier's Route), soaking in the romantic atmosphere and admiring the beautiful architecture of the city.

Enjoy a leisurely lunch at Trattoria da Romano, a historic restaurant known for its fresh seafood and traditional Venetian dishes. Spend your afternoon exploring the iconic sights of Venice, including St. Mark's Square (Piazza San Marco), St. Mark's Basilica (Basilica di San Marco), and the historic Doge's Palace (Palazzo Ducale).

For your final dinner in Italy, indulge in the culinary delights of Antico Pignolo, a renowned restaurant that captures the essence of Venetian cuisine. Afterward, take a relaxing stroll through the less-visited streets of Venice, savoring the magical ambiance of the city's hidden corners and quiet canals.