5-Day Chicago City Adventure with Iconic Landmarks and Culinary Delights Itinerary

Start with a breakfast at Lou Malnati's Pizzeria for a taste of Chicago's famous deep-dish pizza. Then, spend your morning exploring the world-class exhibits at the Art Institute of Chicago with your fast-pass ticket, including the renowned "American Gothic" painting.

Enjoy a lunch at Pequod's Pizza, known for its caramelized crust pizzas. Post-lunch, visit the Field Museum of Natural History to delve into the natural and cultural history of the world, including the fascinating Sue, the T. rex exhibit.

Dine at Gibsons Bar & Steakhouse, a classic Chicago steakhouse. Afterward, take a guided Chicago Gangsters and Ghosts Walking Tour to explore the city's darker history and famous crime spots.

Enjoy a breakfast at Little Goat Diner, known for its creative take on classic diner dishes. Post-breakfast, spend your morning at the serene Lincoln Park & Zoo, one of the oldest zoos in the country, with free admission.

For lunch, head to Kuma's Corner for their legendary burgers. Afterward, explore the vibrant shopping and dining district of The Magnificent Mile, where you can find everything from luxury boutiques to local Chicago flavors.

Indulge in a dinner at Girl & the Goat, offering a menu with bold flavors and a lively atmosphere. Cap off your evening with a visit to the historic Chicago Theatre for a behind-the-scenes tour to learn about its rich history and stunning architecture.

Start your day with a family-friendly breakfast at Portillo's Hot Dogs, a Chicago institution. Then, head to the Navy Pier for a morning of fun, including rides at the amusement park, exploring the Chicago Children's Museum, and enjoying the lakefront views.

Have a lunch at Smoque BBQ, known for its mouthwatering barbecue. Afterward, continue your family adventure with a visit to the Museum of Science and Industry, where you can interact with hands-on exhibits and explore the U-505 Submarine.

For dinner, savor the flavors at Xoco, offering a menu of Mexican street food-inspired dishes. Afterward, take a break from the city buzz and enjoy a serene evening at Grant Park, known as Chicago's "front yard," with its iconic Buckingham Fountain.

Enjoy a breakfast at Eataly Chicago, an Italian marketplace with various dining options. Post-breakfast, take a morning stroll at the Millennium Park, where you can't miss the famous Cloud Gate sculpture, also known as "The Bean."

For your final lunch in Chicago, head to Au Cheval for their renowned burger. Afterward, visit the historic Wrigley Field for a guided tour to learn about its storied past and its significance in Chicago's sports history.

Conclude your Chicago adventure with a memorable dinner at Longman & Eagle, known for its innovative American fare. Afterward, if time allows, take a private Helicopter Tour of Chicago Skyline to see the city from a breathtaking aerial perspective.