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5-Day Chicago City Explorer Itinerary Itinerary
Last updated: 2024 Jun 14Iconic Chicago Landmarks and River Cruise
Morning
Start your Chicago adventure with a delightful breakfast at The Gage, known for its upscale American cuisine. Afterward, take a stroll to the historic Wrigley Building and then explore the shopping paradise of The Magnificent Mile.
Afternoon
For lunch, head to State and Lake Chicago Tavern for a modern gastropub experience. Spend your afternoon at the vibrant Navy Pier, enjoying the various attractions and the stunning views of Lake Michigan.
Evening
Dine at Cindy's Rooftop, offering a panoramic view of the city skyline. Cap off the evening with a Chicago River 1.5-Hour Guided Architecture Cruise, witnessing the renowned architectural wonders of Chicago.
Bedtime
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Art and Skyline Views
Morning
Enjoy a classic Chicago breakfast at Miller's Pub, a historic spot in the Loop. Then, immerse yourself in the world of art at the iconic Art Institute of Chicago, home to a vast collection of masterpieces.
Afternoon
Have a quick bite at Five Star Bar, a local favorite for its casual ambiance. Spend your afternoon at the Millennium Park, where you can't miss the famous "Bean" (Cloud Gate) and the serene Lurie Garden.
Evening
Experience the city from above at the 360 Chicago Observation Deck (Formerly John Hancock Observatory), and then savor a sumptuous dinner at 676 Restaurant & Bar, known for its modern American cuisine.
Bedtime
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Family-Friendly Fun and Evening Riverwalk
Morning
Start with a family-friendly breakfast at The Beetle Bar and Grill. Then, head to the Chicago 45-Minute Family-Friendly Architecture River Cruise for an informative and entertaining ride.
Afternoon
Grab a quick lunch at Old Town Pour House (Old Town - Chicago) before spending your afternoon at the Lincoln Park & Zoo, one of the oldest zoos in the country.
Evening
Enjoy a leisurely walk along the Chicago Riverwalk, taking in the lively atmosphere and the beautiful city lights. For dinner, try the innovative dishes at Bar Mar by José Andrés.
Bedtime
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Museum Day and Evening Delights
Morning
Have a hearty breakfast at Plymouth Restaurant & Rooftop Bar before starting your day at the Field Museum, where you can explore natural history and cultural exhibits.
Afternoon
Grab a quick bite at Fadó Irish Pub and then visit the Shedd Aquarium, known for its impressive aquatic displays.
Evening
Dine at LUXBAR, offering a sophisticated yet casual dining experience. Afterward, take a relaxing Chicago Lake Michigan Skyline Cruise to admire the city's skyline from the water.
Bedtime
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Parks, History, and Farewell Dinner
Morning
Enjoy breakfast at FireLake Grill House and Cocktail Bar before heading to the serene Grant Park, also known as "Chicago's front yard."
Afternoon
Have lunch at Gilt Bar, a trendy spot with a diverse menu. Spend your afternoon at the Chicago History Museum, diving into the city's rich past.
Evening
Conclude your Chicago journey with a memorable dinner at Sweetwater Tavern & Grille (Michigan Plaza - Chicago), where you can reminisce about your favorite moments in the city.
Bedtime
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