Ultimate 5-Day Chicago Exploration Itinerary

Kick off your day with a hearty breakfast at Au Cheval, famous for its indulgent burgers. Then, head to the Art Institute of Chicago to explore one of the oldest and largest art museums in the country.

For lunch, enjoy a casual yet innovative meal at Little Goat Diner, owned by a James Beard award-winning chef. Afterward, take a leisurely Taste of Chinatown Food Walking Tour to discover the culinary delights of the city's vibrant Chinatown.

As the night falls, take a Windy City Ghosts Hauntings of Chicago tour to uncover the city's spooky history. Conclude the day with a delightful dinner at The Purple Pig, known for its eclectic menu and lively Mediterranean-inspired ambiance.

Start your day with a visit to the Millennium Park, where you can't miss the famous "Bean" at the Cloud Gate. Enjoy breakfast at Lula Cafe, a neighborhood spot known for its creative dishes and artsy vibe.

Explore the Navy Pier, Chicago's iconic lakefront destination. Have lunch at Big Star, a lively spot serving up some of the best tacos in town. Afterward, take a spin on the Centennial Wheel for panoramic views of the city and Lake Michigan.

For dinner, indulge in the flavors of Spain at Cafe Ba-Ba-Reeba!, a long-standing favorite for tapas and sangria. Cap off the evening with a Chicago 360 Chicago Observation Deck Sip and View Ticket, enjoying the city lights with a drink in hand.

Begin with a breakfast at Eataly Chicago, an Italian marketplace offering a variety of fresh and high-quality foods. Then, take the Chicago River 1.5-Hour Guided Architecture Cruise to witness the city's stunning skyline and learn about its famous buildings.

For lunch, head to Giordano's for a true Chicago experience with their famous stuffed deep-dish pizza. Afterward, enjoy a self-guided Chicago Prohibition Speakeasies Bus Tour or Walking Tour to uncover the secret history of the city's underground bars and speakeasies.

Dine at Portillo's Hot Dogs for a classic Chicago meal with their famous hot dogs and Italian beef sandwiches. End the day with a relaxed stroll through the Wrigley Building and Tribune Tower, admiring the architectural beauty of these historic landmarks.

Enjoy a breakfast at Kuma's Corner, a rock music-themed burger bar known for its unique and flavorful creations. Then, visit the Lincoln Park & Zoo for a leisurely morning among the animals and beautiful park landscapes.

For lunch, savor the authentic flavors of barbecue at Smoque BBQ, a local favorite for its slow-smoked meats and mouthwatering sides. Spend your afternoon on a Chicago Mob and Crime Bus Tour, delving into the notorious history of the city's organized crime.

Conclude your trip with an exciting Chicago Blackhawks NHL Game Ticket at United Center if there's a game scheduled. For a final dinner, enjoy the upscale ambiance and prime steaks at Gibsons Bar & Steakhouse, a Chicago institution. Reflect on your trip with a nightcap and stunning city views at the 360 Chicago Observation Deck (Formerly John Hancock Observatory).