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Roam Around

undefined Itinerary

Last updated: 2024 Jun 14

Morning
Start your day with a Chicago River Architecture Tour, which will take you through the heart of the city and give you a glimpse into its rich history and stunning architecture. As you cruise down the river, you'll see some of the city's most iconic buildings, such as the Willis Tower, the Wrigley Building, and the Tribune Tower.
Afternoon
After the cruise, head to the Navy Pier for an afternoon of fun and excitement. The pier offers a variety of attractions, including an amusement park, a Ferris wheel, and an IMAX theater. You can also grab lunch at one of the many restaurants on the pier, such as Harry Caray's Tavern or Bubba Gump Shrimp Co.
Evening
End your day with a Sunset Dinner Cruise on Lake Michigan. This two-hour cruise will take you along the lakefront, offering stunning views of the Chicago skyline as the sun sets. Enjoy a delicious dinner and live music as you soak in the beauty of the city.
Bedtime
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Morning
Spend your morning exploring the city's vibrant neighborhoods, such as Wicker Park, Logan Square, or Pilsen. Each neighborhood has its own unique character and charm, so take your time and enjoy the local shops, restaurants, and street art.
Afternoon
For lunch, head to the Chicago Riverwalk, a scenic promenade that runs along the Chicago River. There are plenty of restaurants and cafes to choose from, such as City Winery, O'Brien's Riverwalk Cafe, or Tiny Tapp & Cafe.
Evening
In the evening, take a Twilight River Cruise to see the city come alive at night. This 90-minute cruise will take you down the Chicago River, offering breathtaking views of the illuminated skyline. Sip on a cocktail as you listen to live commentary about the city's architecture and history.
Bedtime
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Morning
Start your day with a Lakefront Speedboat Tour, which will take you on a thrilling ride along the shores of Lake Michigan. You'll get a unique perspective of the city as you speed past iconic landmarks such as Buckingham Fountain, the Adler Planetarium, and Soldier Field.
Afternoon
After the tour, head to Millennium Park for a picnic lunch. This 25-acre park is home to the famous Cloud Gate sculpture (also known as "The Bean"), as well as numerous other art installations and landmarks.
Evening
End your day with a fireworks cruise on Lake Michigan. This 90-minute cruise will take you out onto the lake to watch the weekly Navy Pier fireworks display. Enjoy a drink and some snacks as you take in the stunning pyrotechnics show.
Bedtime
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Morning
Spend your morning at the Museum Campus, home to some of the city's top museums, such as the Field Museum, the Adler Planetarium, and the Shedd Aquarium. Explore the exhibits and learn about everything from dinosaurs to outer space to marine life.
Afternoon
For lunch, head to the River North neighborhood, known for its trendy restaurants and art galleries. Grab a bite at one of the area's many eateries, such as Siena Tavern, RPM Italian, or Eataly.
Evening
End your day with a Chicago Sunset Sail, a two-hour cruise on Lake Michigan that will take you past the city's stunning skyline as the sun sets. Enjoy a glass of wine and some light snacks as you take in the beauty of the city from the water.
Bedtime
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