Ultimate 5-Day Chicago Exploration Itinerary Itinerary

Start your day with a hearty breakfast at Au Cheval, known for its mouthwatering burgers. Then, immerse yourself in art and culture at the world-renowned Art Institute of Chicago with a fast-pass ticket.

Enjoy a scenic lunch at Lula Cafe in Logan Square. Afterward, visit the serene Millennium Park to see the famous Cloud Gate sculpture, also known as "The Bean."

Dine at The Purple Pig, and indulge in a menu of cheese, swine, and wine. End your day with a relaxing stroll at the 360 Chicago Observation Deck Sip and View Ticket, sipping on your favorite beverage as you admire the city lights.

Start with breakfast at Eataly Chicago, where you can explore a variety of Italian cuisines. Then, visit the vibrant The Magnificent Mile for some upscale shopping and the historic Water Tower.

Have lunch at Giordano's for their famous stuffed deep-dish pizza. Spend your afternoon at the family-friendly Navy Pier, exploring the shops, rides, and the beautiful Crystal Gardens.

Dine at RPM Italian for a modern take on traditional Italian dishes. After dinner, enjoy a colorful and musical experience at the Chicago Shakespeare Theater with a performance at one of the city's most vibrant cultural spots.

Start with breakfast at Portillo's Hot Dogs for a classic Chicago meal. Then, take a guided Chicago Gangsters and Ghosts Guided Walking Tour to explore the city's notorious past and haunted history.

Enjoy a diverse and delicious lunch at Smoque BBQ, known for its mouthwatering barbecue. Afterward, take a stroll through the historic Tribune Tower and the nearby Chicago Prohibition Speakeasies Bus Tour or Walking Tour to learn about the city's bootlegging history.

Dine at Girl & the Goat, an award-winning restaurant known for its bold flavors and creative dishes. End your day with a relaxing Taste of Chinatown Food Walking Tour, exploring the culinary delights of one of Chicago's most vibrant neighborhoods.

Start with breakfast at Little Goat Diner, offering a menu of classic comfort foods with a creative twist. Then, spend your morning at the beautiful Lincoln Park & Zoo, exploring the zoo and the surrounding park.

Have a leisurely lunch at Kuma's Corner, known for its gourmet burgers and heavy metal vibe. Afterward, visit the serene Alfred Caldwell Lily Pool to relax and enjoy the peaceful oasis in the heart of the city.

Dine at Longman & Eagle, a Michelin-starred gastropub known for its innovative menu and extensive whiskey selection. End your Chicago journey with a colorful and vibrant Lake Michigan Buffet Brunch, Lunch or Dinner Cruise, enjoying the skyline views and live entertainment on a luxurious cruise.