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4 Days Cultural City Trip in Chicago Itinerary
Last updated: 2024 Jun 14Exploring Downtown Chicago
Morning
Start your day with a visit to Millennium Park. This iconic park is home to the famous Cloud Gate sculpture, also known as 'The Bean'. It's a great spot for photos and a relaxing stroll. Grab breakfast at Wildberry Pancakes and Cafe, known for its delicious pancakes and fresh coffee.
Afternoon
Head over to The Magnificent Mile for some shopping and sightseeing. This bustling avenue is lined with shops, restaurants, and historic landmarks. For lunch, stop by Girl & The Goat, a highly-rated restaurant offering innovative small plates.
Evening
In the evening, catch a show at the historic Chicago Theatre. This iconic venue hosts a variety of performances from concerts to comedy shows. For dinner, dine at Alinea, one of Chicago's most renowned restaurants offering an unforgettable culinary experience.
Bedtime
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4.69Millennium Park
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4.69Millennium Park
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4.65The Magnificent Mile
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4.65The Magnificent Mile
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Cultural Landmarks and Architecture
Morning
Begin your day with a visit to the Chicago Cultural Center. This stunning building offers free art exhibits and performances. Enjoy breakfast at Goddess and the Baker nearby.
Afternoon
Take an architecture river cruise with Chicago Architecture River Cruise Skip-the-Ticket Line. This tour provides an insightful look into Chicago's architectural history. Have lunch at The Purple Pig, known for its Mediterranean-inspired dishes.
Evening
Visit the Rookery Building, one of Chicago's most famous architectural landmarks. End your day with dinner at The Signature Room at the 95th, which offers breathtaking views of the city.
Bedtime
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4.71Chicago Cultural Center
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4.71Chicago Cultural Center
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4.83Chicago Architecture River Cruise Skip-the-Ticket Line
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4.83Chicago Architecture River Cruise Skip-the-Ticket Line
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Museums and Historic Sites
Morning
Start your morning at the Shedd Aquarium, one of the largest indoor aquariums in the world. Enjoy breakfast at Yolk South Loop before heading over.
Afternoon
Explore Grant Park and visit the Art Institute of Chicago using your Chicago Art Institute of Chicago Fast-Pass Ticket. Have lunch at Terzo Piano inside the museum for a delightful meal with a view.
Evening
In the evening, head to House of Blues for live music and dinner. This iconic venue offers great food and an even better atmosphere.
Bedtime
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4.75Shedd Aquarium
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4.75Shedd Aquarium
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4.79Chicago Art Institute of Chicago Fast-Pass Ticket
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4.79Chicago Art Institute of Chicago Fast-Pass Ticket
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Sports and Scenic Views
Morning
Begin your day with a tour of Wrigley Field, one of baseball's oldest ballparks. Have breakfast at Ann Sather Restaurant nearby.
Afternoon
Take a stroll along the scenic Chicago Riverwalk where you can enjoy beautiful views of the city skyline. Stop for lunch at River Roast, which offers fantastic riverside dining.
Evening
End your trip with a visit to United Center to catch a game or concert if there's one scheduled. For dinner, enjoy deep-dish pizza at Lou Malnati's Pizzeria.
Bedtime
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4.86Wrigley Field
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4.86Wrigley Field
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4.72Chicago Riverwalk
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4.72Chicago Riverwalk
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