Ultimate Chicago Experience in 5 Days Itinerary

Indulge in a hearty breakfast at Lou Malnati's Pizzeria, a Chicago staple known for its deep-dish pizza. Afterward, explore the Art Institute of Chicago, home to an impressive collection of art spanning centuries.

For lunch, savor the flavors of Spain at Cafe Ba-Ba-Reeba!. Post-lunch, take a leisurely walk through Millennium Park and marvel at the iconic Cloud Gate (The Bean).

Dive into a unique dining experience at The Purple Pig, known for its Mediterranean-inspired dishes. Conclude the day with a visit to the Chicago Theatre for a show or simply admire its iconic marquee.

Enjoy a classic Chicago breakfast at Portillo's Hot Dogs, famous for its hot dogs and Italian beef sandwiches. Then, immerse yourself in scientific wonders at the Field Museum, where you can explore exhibits on natural history and culture.

For lunch, head to Xoco for a taste of authentic Mexican cuisine by Chef Rick Bayless. Afterward, visit the Shedd Aquarium to discover the fascinating marine life.

Embark on the Chicago Gangsters and Ghosts Guided Walking Tour to uncover the city's darker history. Conclude the evening with a cocktail at the Untitled Supper Club, known for its speakeasy vibe.

Start your day with a delightful breakfast at Little Goat Diner, a favorite spot for comfort food. Then, explore the lush greenery of Lincoln Park & Zoo, home to a variety of animals and beautiful gardens.

For lunch, head to Giordano's for their famous stuffed deep-dish pizza. Post-lunch, visit the Marina City and take a stroll along the Chicago River.

Enjoy a scenic dinner cruise on the Chicago Lake Michigan Buffet Brunch, Lunch or Dinner Cruise, offering stunning views of the city skyline from the water.

Treat yourself to a sumptuous breakfast at Girl & The Goat, known for its innovative dishes. Then, explore the Navy Pier, where you can ride the Centennial Wheel and enjoy the various attractions.

For lunch, head to Au Cheval for their famous burger. Post-lunch, visit the 360 Chicago Observation Deck (Formerly John Hancock Observatory) for breathtaking views of the city.

Conclude your Chicago adventure with a memorable dinner at Gibsons Bar & Steakhouse, a classic steakhouse. Afterward, take a leisurely walk along the Chicago Riverwalk to soak in the city's ambiance.