Ultimate 5-Day Chicago Adventure Itinerary Itinerary

Enjoy a classic Chicago breakfast at The Purple Pig, a renowned spot for its inventive dishes. Afterward, visit the Art Institute of Chicago for a cultural morning, exploring one of the oldest and largest art museums in the United States.

For lunch, head to Giordano's to try their famous stuffed deep-dish pizza. Post-lunch, immerse yourself in the aquatic world at the Shedd Aquarium. Explore the amazing exhibits and catch a live aquatic presentation.

Wind down with a relaxing walk at Navy Pier, known for its entertainment and dining options. Enjoy a sumptuous dinner at Gibsons Bar & Steakhouse, a classic Chicago steakhouse offering prime steaks and seafood.

Start your day with a delightful breakfast at Eataly Chicago, an Italian marketplace with various cafes and restaurants. After breakfast, take a The Chicago Theatre Tour Experience to learn about the rich history and stunning architecture of this famous venue.

For lunch, visit Minneapolis, Minnesota to experience the vibrant and diverse culinary scene of this neighboring city. Afterward, spend your afternoon at the Museum of Science and Industry, exploring the interactive exhibits and learning about fascinating scientific innovations.

Conclude your day with a dinner at Little Goat Diner, a casual spot known for its creative menu. Afterward, enjoy a live performance at a local theater or live music venue to immerse yourself in Chicago's vibrant arts scene.

Kick off your morning with a visit to Cafe Ba-Ba-Reeba! for a Spanish-style breakfast. Post-breakfast, take a Chicago Hop-on Hop-off Sightseeing Tour by Open-top Bus to get an overview of the city's top attractions and neighborhoods.

For lunch, head to Big Star for some of the best tacos in town. After lunch, embark on a journey through Chicago's culinary history with the Chicago Prohibition Speakeasies Bus Tour or Walking Tour. Explore hidden bars and learn about the city's bootlegging past.

Enjoy a sophisticated dinner at Longman & Eagle, known for its Michelin-star rated cuisine. Afterward, take a leisurely walk through the Chicago Medieval Torture Museum and engage in some ghost hunting to uncover the city's darker history.

Begin your final day with a hearty breakfast at Kuma's Corner, a rock 'n' roll bar known for its gourmet burgers. After breakfast, visit the Lincoln Park & Zoo for a morning of wildlife and nature, exploring one of the oldest zoos in the United States.

For lunch, enjoy the casual and comforting atmosphere of Smoque BBQ, known for its authentic, wood-smoked Texas-style barbecue. Post-lunch, take a stroll through the lush landscapes of Grant Park and visit the iconic Buckingham Fountain for some memorable photos.

Conclude your trip with a visit to the Chicago Field Museum of Natural History, immersing yourself in the world of natural science and history. For a final dinner, savor the flavors of Portillo's Hot Dogs, a Chicago institution known for its classic hot dogs and Italian beef sandwiches.