5-Day Chicago Cultural and Culinary Adventure Itinerary

Start your day with a delicious breakfast at Lou Malnati's Pizzeria, a Chicago institution known for its deep-dish pizza. After breakfast, visit the world-renowned Art Institute of Chicago with a fast-pass ticket and explore its impressive collection of art and artifacts.

Enjoy a VIP tour or explore at your own pace at the Field Museum, where you can learn about natural history and cultural anthropology. For lunch, try the famous caramelized crust pizza at Pequod's Pizza.

Experience the vibrant atmosphere and innovative cuisine at Girl & the Goat, a top-rated restaurant in the West Loop. After dinner, take a guided walking tour to discover the city's gangster and ghost stories on the Chicago Gangsters and Ghosts Guided Walking Tour.

Start your day with a visit to the historic Wrigley Field, home of the Chicago Cubs. Then, enjoy a hearty breakfast at Smoque BBQ, known for its mouthwatering smoked meats.

Explore the vibrant neighborhood of Logan Square and grab lunch at Little Goat Diner, a casual spot with a creative menu. Afterward, take a guided Chicago Gourmet Brunch, Lunch, or Dinner River Cruise and enjoy the city's skyline from the water.

Dine at Gibsons Bar & Steakhouse, a classic Chicago steakhouse with a lively atmosphere. After dinner, take a stroll through the lively atmosphere of Navy Pier and consider riding the iconic Ferris wheel.

Enjoy a classic Chicago breakfast at Portillo's Hot Dogs, known for its hot dogs and Italian beef sandwiches. Afterward, take a guided tour of the Chicago Theatre and learn about its rich history and stunning architecture.

Visit the iconic Willis Tower Skydeck and The Ledge and step out onto the glass-floored balconies for a thrilling experience. For lunch, head to Xoco for gourmet Mexican cuisine by Rick Bayless.

Indulge in a memorable dining experience at Au Cheval, famous for its award-winning burgers and upscale diner ambiance. Afterward, enjoy a live performance at a local venue or take a Prohibition Speakeasies Bus Tour or Walking Tour to learn about Chicago's history of bootlegging and speakeasies.

Start your day with a visit to the beautiful Lincoln Park & Zoo, where you can enjoy a morning stroll and see a variety of animals. For breakfast, try the pastries and coffee at Eataly Chicago, a vibrant Italian marketplace.

Explore the expansive Grant Park and visit the serene Museum of Science and Industry with an audio guide. For lunch, indulge in the creative burgers at Kuma's Corner, a rock music-themed eatery.

Conclude your Chicago journey with a memorable dinner at Girl & the Goat, where you can savor bold flavors and innovative dishes. Afterward, take a relaxing evening walk through Millennium Park and enjoy the iconic Cloud Gate sculpture, also known as "The Bean."