Ultimate 5-Day Chicago Exploration Itinerary Itinerary

Start with a delightful breakfast at Lula Cafe in Logan Square, known for its farm-to-table concept. Then, head to the Field Museum to explore natural history and anthropology, including the famous Sue the T. rex.

Enjoy a leisurely lunch at The Purple Pig, offering a menu of cheese, swine, and wine. Afterward, visit the nearby Shedd Aquarium to witness amazing aquatic life from around the world.

Dine at RPM Italian, where celebrity sightings are as common as the mouthwatering dishes. Cap off the night with a serene walk through Millennium Park, taking in the iconic Cloud Gate sculpture, also known as "The Bean."

Indulge in a delicious breakfast at Eataly Chicago, an Italian marketplace with a variety of high-quality food options. Afterward, immerse yourself in art at the renowned Art Institute of Chicago, enjoying priority access with your fast-pass ticket.

For lunch, head to Xoco and savor the flavors of Mexico with their mouthwatering street food. Then, experience the city from new heights at the 360 Chicago Observation Deck (Formerly John Hancock Observatory), where you'll have a panoramic view of Chicago's skyline.

Dine at Girl & the Goat, an award-winning restaurant known for its bold flavors and innovative dishes. After dinner, take a relaxing stroll down The Magnificent Mile, Chicago's premier shopping destination.

Start your day with a breakfast of champions at Au Cheval, famous for its indulgent yet delicious menu. Then, embark on the Chicago Prohibition Speakeasies Bus Tour or Walking Tour to learn about the city's fascinating history.

Enjoy a casual lunch at Little Goat Diner, a contemporary diner with a menu that reflects the best of American comfort food. Follow it up with a visit to the Chicago 360 Chicago Observation Deck Skip-the-Line Ticket for breathtaking views.

For dinner, head to Gibsons Bar & Steakhouse for a classic Chicago steak experience. Cap off the night with a visit to Skydeck Chicago at Willis Tower (Sears Tower) and step out onto The Ledge for an exhilarating experience.

Kick off your final day with a delightful breakfast at Longman & Eagle in Logan Square, known for its Michelin-starred cuisine. Then, take a guided stroll through the city's diverse neighborhoods on the Chicago Favorite Foods Guided Walking Tour.

Enjoy a laid-back lunch at Kuma's Corner, famous for its gourmet burgers and heavy metal vibe. Spend your afternoon visiting the animals at the historic Lincoln Park & Zoo, followed by a leisurely walk through the scenic park.

Dine at Smoque BBQ for some of the best barbecue in the city, and then catch a performance at the iconic Chicago Theatre, known for its stunning architecture and rich history.