Ultimate 7-Day Chicago and Italy Adventure Itinerary

Begin with a hearty breakfast at Wildberry Pancakes and Cafe, offering a wide selection of pancakes. Then, explore the interactive exhibits at the Museum of Science and Industry.

Have a quick bite at Eataly Chicago, a vibrant Italian marketplace, and then visit the aquatic wonders at the Shedd Aquarium. Later, take a leisurely walk at Navy Pier and enjoy the attractions.

Dine at RPM Italian, where celebrity chef Bill and Giuliana Rancic offer a modern take on Italian cuisine. End the night with a stroll at the serene Chicago Lakefront Trail.

Start with breakfast at Lula Cafe, a neighborhood spot known for its seasonal dishes. Then, take a walk through the vibrant Wicker Park Neighborhood.

Enjoy a diverse range of flavors on the Chicago Favorite Foods Guided Walking Tour. Sample iconic dishes while exploring the city's neighborhoods. For a post-tour snack, visit Big Star for their renowned tacos.

Savor an unforgettable dinner at Au Cheval, famous for its award-winning cheeseburger. Afterward, explore the lively Fulton Market District and its trendy bars.

Begin your day in Milan with a delightful breakfast at Pasticceria Marchesi 1824, one of the city's oldest pastry shops. Then, marvel at the impressive architecture of the Milan Cathedral (Duomo).

After visiting the cathedral, enjoy a sumptuous lunch at Terrazza Triennale, which offers not only exquisite cuisine but also a panoramic view of the city. Spend your afternoon exploring the masterpieces at the Pinacoteca di Brera, one of Italy's most important art galleries.

For dinner, indulge in the innovative dishes at Da Vittorio, a three-Michelin-starred restaurant known for its impeccable service. Conclude your day with a leisurely walk around the picturesque Galleria Vittorio Emanuele II, one of the world's oldest shopping malls.

Start your day in Bologna with a traditional Italian breakfast at Caffè Terzi. Then, take a stroll through the historic heart of the city, visiting landmarks such as the Piazza Maggiore and the Basilica di San Petronio.

For lunch, enjoy the rich flavors of Bolognese cuisine at Trattoria Anna Maria, a local favorite. Afterward, explore the unique history of the city at the Museo della Storia di Bologna (Museum of the History of Bologna) or take a leisurely walk along the Portico di San Luca, the longest covered arcade in the world.

Dine at I Portici Hotel Bologna, where you can enjoy a meal in a sophisticated setting with innovative dishes. Finish the day with a relaxing evening passeggiata (stroll) along the charming streets of La Dotta, La Grassa, La Rossa, Bologna's well-known nicknames.

Begin your day in Venice with a delightful breakfast at Caffè Florian, the oldest café in the world. Then, take a gondola ride along the Grand Canal, admiring the stunning architecture and passing under the iconic bridges of Venice.

After the gondola ride, enjoy a sumptuous lunch at Osteria Da Fiore, a Michelin-starred restaurant known for its exquisite seafood dishes. Spend your afternoon exploring the cultural treasures of Venice, including the St. Mark's Basilica (Basilica di San Marco) and the Doge's Palace (Palazzo Ducale).

For dinner, indulge in the innovative dishes at Quadri Restaurant & Cafè, a Michelin-starred restaurant with a breathtaking view of St. Mark's Square. Conclude your day with a romantic stroll through the hidden alleys and charming piazzas of Venice.

Start your last day with a delightful breakfast at Beatrix, offering a variety of healthy and delicious options. Then, head to the iconic Willis Tower (Sears Tower) and step out onto The Ledge for a heart-pounding, glass-floored view of the city.

Enjoy a classic Chicago hot dog for lunch at Portillo's Hot Dogs, and then spend your afternoon at the Lincoln Park Zoo, a beautiful and family-friendly destination.

Dine at Girl & the Goat, an award-winning restaurant serving bold flavors in a lively setting. Finish your trip with a memorable comedy show at The Second City, known for launching the careers of many famous comedians.