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

Fuel up for the day with a hearty breakfast at Au Cheval, famous for its indulgent burgers and a lively atmosphere. Post-breakfast, take a leisurely walk to the historic Wrigley Building and then explore the upscale boutiques of The Magnificent Mile.

Enjoy a Chicago-style deep-dish pizza for lunch at Lou Malnati's Pizzeria, a local favorite. Afterward, immerse yourself in art and history at the renowned Art Institute of Chicago with a fast-pass ticket.

Experience the vibrant culinary scene of Chicago at Girl & the Goat, known for its creative dishes and a lively atmosphere. Conclude your evening with a visit to the iconic Chicago Theatre for a guided tour experience.

Start your day with a breakfast at Little Goat Diner, a casual spot with a diverse menu. After breakfast, visit the serene Millennium Park to see the famous Cloud Gate sculpture, also known as "The Bean."

Enjoy a leisurely lunch at Giordano's, where you can savor their famous stuffed deep-dish pizza. Post-lunch, explore the aquatic wonders at the Shedd Aquarium and the natural history exhibits at the Field Museum with a single ticket or VIP tour.

Dine at Gibsons Bar & Steakhouse, an iconic Chicago steakhouse offering prime steaks and classic cocktails. After dinner, take a relaxing walk at the Navy Pier and enjoy the stunning views of Lake Michigan.

Begin your day with a breakfast at Portillo's Hot Dogs, a Chicago institution known for its classic hot dogs and Italian beef sandwiches. After breakfast, embark on a guided Chicago Gangsters and Ghosts Walking Tour to uncover the city's intriguing past.

For lunch, head to Smoque BBQ and indulge in some of the best barbecue in the city. Afterward, take a self-guided stroll through the Chicago Pedway & Downtown Secrets Walking Tour to discover hidden gems and architectural wonders.

Enjoy a sophisticated dinner at Eataly Chicago, an Italian marketplace with multiple dining options. Cap off the evening with a visit to the Skydeck Chicago at Willis Tower (Sears Tower) and dare to step out onto The Ledge for a thrilling experience.

Start your final day with a breakfast at Longman & Eagle, a Michelin-starred gastropub known for its innovative cuisine. After breakfast, take a morning stroll through the lush greenery of Grant Park and visit the serene oasis of Buckingham Fountain.

For your last lunch in Chicago, enjoy the unique flavors of Xoco, a Rick Bayless restaurant specializing in Mexican street food and artisanal tortas. Afterward, spend your afternoon at the Lincoln Park Zoo, one of the oldest and most beautiful zoos in the country.

Conclude your Chicago journey with a grand dinner at Kuma's Corner, famous for its heavy metal vibe and gourmet burgers. Reflect on your trip as you enjoy the eclectic decor and the bold flavors of the food.