Ultimate 5-Day Chicago Adventure with Top Attractions and Culinary Delights Itinerary

Start with a hearty breakfast at 676 Restaurant & Bar. Then, immerse yourself in culture at the Art Institute of Chicago with a fast-pass ticket, avoiding the lines.

Have a leisurely lunch at Cindy's Rooftop with its vibrant atmosphere and great views. Spend your afternoon at Navy Pier, exploring the shops, rides, and the Centennial Wheel for a bird's-eye view of the city.

Dine at Staytion Market & Bar, offering a modern take on comfort food. Afterward, enjoy the Chicago Signature Food Tasting & Cultural Walking Tour to savor the city's culinary delights.

Have a family-friendly breakfast at Elephant & Castle. Then, enjoy a morning at the Lincoln Park Zoo, one of the oldest zoos in the US, with free admission.

Grab a quick bite at Billy Goat Tavern (Millennium Park) before visiting the interactive exhibits at the Chicago Museum of Science and Industry.

Experience the Chicago Gourmet Brunch, Lunch, or Dinner River Cruise with live music and a tour of the city's architecture from the water. For a late-night drink, head to Long Room Chicago, a cozy neighborhood bar.

Enjoy a breakfast at The Gage, known for its rustic, yet refined, cuisine. Start your day with a visit to the Chicago Theatre for a behind-the-scenes tour of this iconic venue.

For lunch, indulge in the upscale American fare at Travelle at The Langham, Chicago. Afterward, explore the Chicago Prohibition Speakeasies Bus Tour or Walking Tour to learn about the city's notorious past.

Dine at The Franklin Room, a modern speakeasy with a vintage vibe. Then, if you dare, join the Chicago Gangsters and Ghosts Guided Walking Tour to uncover the dark and mysterious history of Chicago's criminal underworld.

Enjoy a breakfast at FireLake Grill House and Cocktail Bar, offering a diverse menu with a focus on local ingredients. Afterward, take in the city views from the Skydeck Chicago at Willis Tower (Sears Tower) and step out onto The Ledge for an exhilarating experience.

Have a laid-back lunch at Miller's Pub, a historic bar and restaurant in the heart of downtown. Spend your afternoon at the John Hancock Center with a skip-the-line ticket to the 360 Chicago Observation Deck, enjoying both the views and a drink at the bar.

Conclude your Chicago adventure with a memorable dinner at Cherry Circle Room, located in the historic Chicago Athletic Association. Reflect on your trip as you savor the innovative, seasonal dishes in a timeless setting.