5-Day Chicago Adventure: Landmarks, Cruises, and Culinary Delights Itinerary

Enjoy a delightful breakfast at Lula Cafe before heading to the Chicago Art Institute of Chicago. Spend the morning exploring the museum's world-class art collection.

For lunch, indulge in the delectable dishes at The Purple Pig. Afterward, visit the 360 Chicago Observation Deck (Formerly John Hancock Observatory) for breathtaking views of the city.

Dine at the elegant The Signature Room at the 95th and enjoy panoramic views of Chicago. After dinner, take a leisurely walk in Millennium Park and admire the famous "Bean" sculpture.

Start your day with a hearty breakfast at Little Goat Diner. Then, visit the Field Museum to explore its fascinating exhibits.

For lunch, enjoy the mouthwatering burgers at Au Cheval. Afterward, take a relaxing walk along the Chicago Lake Michigan Skyline Cruise and enjoy the beautiful lakefront views.

Dine at the renowned Girl & The Goat for a memorable culinary experience. After dinner, take a stroll in Grant Park and admire the Buckingham Fountain.

Enjoy a delicious breakfast at Kuma's Corner, known for its unique and flavorful burgers. Then, embark on a Chicago Gangsters and Ghosts Guided Walking Tour to learn about the city's intriguing history.

For lunch, savor the mouthwatering barbecue at Smoque BBQ. Afterward, explore the Navy Pier and take a ride on the Chicago Navy Pier Centennial Wheel Regular & Express Ticket for stunning views of the city.

Dine at the iconic Gibsons Bar & Steakhouse for a classic Chicago steakhouse experience. Afterward, enjoy a live performance at the historic Chicago Theatre.

Start your day with a delightful breakfast at Big Star. Then, take a guided tour of the city's diverse neighborhoods, such as Pilsen, Chinatown, and Wicker Park.

For lunch, enjoy the authentic Mexican cuisine at Xoco. Afterward, visit the vibrant Wrigley Field and take a guided tour of this historic baseball stadium.

Conclude your Chicago adventure with a farewell dinner at Eataly Chicago, where you can savor a variety of Italian dishes. Afterward, take a relaxing evening walk along the Chicago River and reminisce about your memorable trip.