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Family Fun Weekend in Chicago

Family Fun Weekend in Chicago Itinerary

Last updated: 2024 Jun 14

Iconic Landmarks and River Cruise

Morning
Start your Chicago adventure with breathtaking views from the 360 Chicago Observation Deck (Formerly John Hancock Observatory). Afterward, enjoy a hearty breakfast at State and Lake Chicago Tavern.
Afternoon
Spend your afternoon cruising along the Chicago River on an architectural tour, admiring the city's famous buildings. For lunch, head to Cindy's Rooftop for a unique dining experience with panoramic views.
Evening
As the sun sets, take a leisurely walk at Navy Pier, where you can enjoy the amusement park rides and the evening breeze from Lake Michigan. Have dinner at The Gage, known for its diverse menu and historic setting.
Bedtime
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Museums and Millennium Park

Morning
Immerse yourself in art and history at the Art Institute of Chicago and the nearby Grant Park. Grab a quick breakfast at Plymouth Restaurant & Rooftop Bar before starting your day.
Afternoon
After the museums, take a relaxing stroll through the serene Millennium Park, where you can't miss the famous "Bean" (Cloud Gate). For lunch, head to The Gage for their renowned Scotch eggs.
Evening
Conclude your trip with a visit to the lively Chicago Cultural Center, followed by a delightful dinner at Cindy's Rooftop with its stunning views of the city skyline.
Bedtime
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