7-Day Chicago and Great Lakes Adventure Itinerary

Enjoy a gourmet breakfast at Alinea, a three-Michelin-star restaurant. Afterward, spend your morning exploring the masterpieces at the Art Institute of Chicago with a fast-pass ticket.

Have a leisurely lunch at Eataly Chicago, an Italian marketplace with various dining options. Post-lunch, visit the Millennium Park to see the famous "Bean" sculpture, also known as Cloud Gate, and take in the park's other unique art installations.

Indulge in a progressive dinner experience with the Chicago Gourmet Brunch, Lunch, or Dinner River Cruise. This cruise will take you along the Chicago River while you enjoy a fine dining experience with live music and breathtaking views of the city.

Start your day with a breakfast sandwich at Little Goat Diner, a casual spot with a creative menu. After breakfast, join the Chicago Gangsters and Ghosts Guided Walking Tour to uncover the city's underworld history and haunted locations.

For lunch, head to Big Star for their renowned tacos and a relaxed atmosphere. Afterward, take a guided tour of the Chicago Theatre to learn about its rich history and contributions to the world of entertainment.

Dine at The Publican, known for its beer selection and pork-centric menu. After dinner, experience the city's nightlife by visiting some of the best bars in the Fulton Market District, such as The Aviary for innovative cocktails or Parlor Pizza Bar for a more laid-back vibe.

Have a family-friendly breakfast at Portillo's Hot Dogs, a Chicago institution. Then, spend the morning at Navy Pier, exploring the various attractions and enjoying the lakeside views.

Grab a quick bite at Kuma's Corner, known for its heavy metal-inspired burgers, before heading to the Lincoln Park Zoo for a relaxed afternoon with the animals.

For dinner, try the unique flavors at Xoco, specializing in Mexican street food. Afterward, enjoy a fun-filled evening at Medieval Torture Museum Ticket with Ghost Hunting, a quirky and entertaining experience for the whole family.

Start your day with a breakfast sandwich at Crisp, known for its Korean-inspired dishes. After breakfast, visit the iconic Wrigley Field for a guided tour and a glimpse into the history of Chicago's baseball.

Enjoy a Chicago-style hot dog for lunch at Giordano's, then take a Private Helicopter Tour of Chicago Skyline for a breathtaking aerial view of the city's skyline and famous landmarks.

Dine at Frontera Grill, a vibrant and colorful restaurant offering the best of Mexican cuisine. After dinner, take a relaxing walk along the Chicago River to cap off the day.

Have a hearty breakfast at Smoque BBQ, known for its authentic barbecue flavors. After breakfast, start your day with a visit to the Adler Planetarium, where you can explore the wonders of the universe.

For lunch, head to Revival Food Hall, a lively food hall with a variety of culinary options. Post-lunch, immerse yourself in the natural world at the Shedd Aquarium, home to a diverse range of marine life.

Enjoy a relaxing dinner at Lula Cafe, a neighborhood spot known for its farm-to-table dishes. Afterward, take a serene evening walk through Grant Park, also known as Chicago's "front yard," and enjoy the city lights.

Start your last day with a classic Chicago breakfast at The Original Pancake House, known for its wide selection of breakfast delights. After breakfast, take a final stroll through the city and visit any favorite spots for some last-minute souvenirs or memories.

For lunch, enjoy the famous pan pizza at Pequod's Pizza, a local favorite. Afterward, take the Chicago Prohibition Speakeasies Bus Tour or Walking Tour to learn about the city's history during the Prohibition era and visit hidden bars with a knowledgeable guide.

Conclude your Chicago journey with a grand dinner at Girl & the Goat, an award-winning restaurant with a menu that celebrates bold flavors and local ingredients. After dinner, reflect on your trip with a peaceful evening at Skydeck Chicago at Willis Tower (Sears Tower), standing on the famous Ledge and looking out over the city one last time.