5-Day Chicago Highlights and Culinary Delights Itinerary

Start with a gourmet brunch on a Chicago Gourmet Brunch River Cruise with live jazz music, courtesy of Spirit of Chicago. Afterward, visit the renowned Art Institute of Chicago with a fast-pass ticket to beat the lines.

Immerse yourself in natural history at the Field Museum, and then take a break at Eataly Chicago, an Italian marketplace with various dining options. Post-lunch, explore the marine life at the nearby Shedd Aquarium.

Dine at Gibsons Bar & Steakhouse, a Chicago classic known for its prime steaks and extensive wine list. After dinner, take a relaxing walk in Millennium Park and don't miss the famous "Bean" (Cloud Gate) sculpture.

Enjoy a hearty breakfast at Lula Cafe in Logan Square, then spend the morning exploring the area's vibrant street art and local boutiques. Don't miss the chance to take a photo at the iconic Logan Square Monument.

For lunch, head to Xoco for some of the best Mexican street food in the city. Afterward, take a guided Chicago Gangsters and Ghosts Walking Tour to uncover the city's darker history and hidden secrets.

Indulge in a pre-theater dinner at The Chicago Theatre, where you can enjoy a meal in the historic theater before catching a live performance. After the show, take a leisurely stroll through the bustling streets of downtown.

Start your day with a breakfast sandwich at Little Goat Diner, then spend the morning at Lincoln Park & Zoo, one of the oldest zoos in the country. Explore the park and visit the animals in their habitats.

For lunch, head to Smoque BBQ for some of the best barbecue in the city. Afterward, take a leisurely bike ride or walk along the lakefront and enjoy the beautiful views of Lake Michigan.

Dine at Girl & the Goat, a highly acclaimed restaurant known for its bold flavors and innovative dishes. After dinner, relax at a nearby lounge or rooftop bar and enjoy the Chicago skyline at night.

Enjoy a classic Chicago breakfast at Portillo's Hot Dogs, then take a guided Taste of Chinatown Food Walking Tour to sample a variety of Asian cuisine and learn about the history of the neighborhood.

Spend your afternoon at Willis Tower Skydeck, where you can step out onto The Ledge and take in breathtaking views of the city. For lunch, try the famous caramelized crust pizza at Pequod's Pizza.

Dine at Au Cheval, known for its award-winning cheeseburger, and then end your trip with a special experience at The Second City, the famous comedy club where many comedy legends got their start.