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Chicago, Illinois, USA

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

Published: 2024 Jan 04
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Iconic Chicago Landmarks and River Cruise

Morning
Begin your Chicago journey with a delightful breakfast at State and Lake Chicago Tavern, known for its classic American cuisine. Afterward, take a stroll along the Chicago Riverwalk and admire the city's stunning architecture.
Afternoon
For lunch, head to Billy Goat Tavern (The Original) for their famous "Cheezborger." Spend your afternoon at the historic Wrigley Building and explore the shops on The Magnificent Mile.
Evening
Enjoy a sophisticated dinner at Terrace 16, offering panoramic views of the city. Cap off the evening with a Chicago 360 Chicago Observation Deck Sip and View Ticket to see Chicago's skyline at night.
Bedtime
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Museum Marvels and Navy Pier Fun

Morning
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.
Afternoon
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.
Evening
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.
Bedtime
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Family-Friendly Chicago and Evening River Cruise

Morning
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.
Afternoon
Grab a quick bite at Billy Goat Tavern (Millennium Park) before visiting the interactive exhibits at the Chicago Museum of Science and Industry.
Evening
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.
Bedtime
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Chicago's Cultural Side and Haunted History

Morning
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.
Afternoon
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.
Evening
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.
Bedtime
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Sky-high Thrills and Culinary Delights

Morning
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.
Afternoon
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.
Evening
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.
Bedtime
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