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

Start your day with a visit to the world-renowned Art Institute of Chicago, where you can use your fast-pass ticket to explore the impressive collections. After immersing yourself in art, enjoy a brunch at The Purple Pig, offering a menu of cheese, swine, and wine in a lively setting.

Post-brunch, take a leisurely walk to Millennium Park to see the famous "Bean" sculpture and the serene Lurie Garden. Then, indulge in a guided Chicago Favorite Foods Walking Tour to savor the city's culinary highlights, including local favorites and hidden gems.

For dinner, experience the vibrant atmosphere and innovative dishes at Girl & the Goat, a highly acclaimed restaurant. Afterward, enjoy a leisurely stroll along the Chicago Riverwalk, taking in the beautiful views of the city lights and the river's architecture.

Fuel up for the day with a hearty breakfast at Lou Malnati's Pizzeria, a Chicago classic known for its deep-dish pizza. After breakfast, take a guided Chicago Gangsters and Ghosts Walking Tour to explore the city's notorious past and visit famous crime scenes.

After the tour, enjoy a visit to the Field Museum, where you can use your VIP tour ticket to delve into natural history and cultural exhibits. For lunch, head to Giordano's to indulge in another Chicago staple, the stuffed deep-dish pizza.

Dine at Gibsons Bar & Steakhouse, an iconic Chicago steakhouse offering prime steaks and an extensive wine list. After dinner, if you're up for some entertainment, catch a show at the historic Chicago Theatre or explore the nearby vibrant nightlife.

Enjoy a serene morning at Adler Planetarium, where you can explore the universe and enjoy the stunning views of Lake Michigan. For breakfast, visit Little Goat Diner, a popular spot known for its creative take on classic diner fare.

Post-breakfast, take a leisurely walk through Grant Park and make your way to the Shedd Aquarium, where you can use your ticket to discover a diverse array of aquatic species. For lunch, savor the flavors of authentic Mexican cuisine at Big Star in Wicker Park.

As the day winds down, enjoy a laid-back dinner at Portillo's Hot Dogs, a Chicago institution famous for its hot dogs and Italian beef sandwiches. Afterward, take a relaxing evening stroll along the Chicago Riverwalk or explore the vibrant neighborhood of River North.

Start your final day with a breakfast at Xoco, a Rick Bayless restaurant known for its gourmet Mexican street food. After breakfast, visit the iconic Willis Tower Skydeck and The Ledge to step out onto the glass-floored balconies and enjoy unparalleled views of the city.

For lunch, head to Smoque BBQ to indulge in some of the best barbecue in the city. Afterward, take a guided Chicago Prohibition Speakeasies Walking Tour to learn about the city's history during the Prohibition era and visit hidden bars with a local guide.

Conclude your Chicago adventure with a memorable dinner at Au Cheval, known for its famous cheeseburger and upscale diner ambiance. After dinner, if you have time, take a leisurely walk through the vibrant streets of the West Loop and enjoy the neighborhood's lively atmosphere.