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5 Days in Chicago Illinois Itinerary
Last updated: 2024 Jun 14Welcome to the Windy City
Morning
Start your day with a visit to the iconic Skydeck Chicago at Willis Tower (Sears Tower). Enjoy breathtaking views of the city from one of the tallest buildings in the world. For breakfast, head to Lou Mitchell's, a classic Chicago diner known for its hearty breakfasts.
Afternoon
Explore the fascinating exhibits at the Field Museum, one of the largest natural history museums in the world. For lunch, enjoy a meal at The Gage, an upscale tavern offering American cuisine with a twist.
Evening
End your day with some live music at House of Blues, a famous venue for blues and other genres. Before that, have dinner at Girl & The Goat, a highly-rated restaurant known for its innovative dishes.
Bedtime
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4.27Skydeck Chicago at Willis Tower (Sears Tower)
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4.27Skydeck Chicago at Willis Tower (Sears Tower)
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4.56Field Museum
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4.56Field Museum
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Exploring Downtown Chicago
Morning
Begin your day with a visit to Millennium Park, home to the famous Cloud Gate sculpture (The Bean). Grab breakfast at Wildberry Pancakes and Cafe, known for its delicious pancakes and other breakfast items.
Afternoon
Take a stroll along the scenic Chicago Riverwalk and enjoy lunch at Café Bonhomme, which offers great views and Mediterranean-inspired dishes. Afterward, explore the historic Chicago Theatre and take a guided tour.
Evening
Catch an evening show at Second City, Chicago's legendary comedy club. Before that, dine at RPM Italian, renowned for its modern Italian cuisine.
Bedtime
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4.69Millennium Park
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4.69Millennium Park
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4.72Chicago Riverwalk
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4.72Chicago Riverwalk
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Cultural Gems and Lakefront Views
Morning
Visit the impressive collection of art at the Art Institute of Chicago. Start your morning with breakfast at The Bongo Room, famous for its creative brunch dishes.
Afternoon
Head over to the lakefront and explore the wonders of marine life at the Shedd Aquarium. For lunch, stop by Giordano's for some classic deep-dish pizza.
Evening
Spend your evening enjoying breathtaking views from the 94th floor of 360 Chicago Observation Deck (Formerly John Hancock Observatory) . Have dinner beforehand at The Signature Room at the 95th, which offers both excellent food and panoramic views.
Bedtime
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4.61Art Institute of Chicago
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4.61Art Institute of Chicago
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4.75Shedd Aquarium
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4.75Shedd Aquarium
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Historic Architecture and Sports Fever
Morning
Start your day by exploring architectural marvels like the historicRookery BuildingandMarina City[26036]. Enjoy breakfast nearby atYolk - South Loopfor hearty morning fare.
Afternoon
Dive into sports history with a visit toWrigley Field[1216],one of baseball's oldest stadiums. Grab lunch around Wrigleyville area,Old Crow Smokehousefor BBQ delights.
Evening
Wrap up your day by catching an event or game if available,United Center[22646]. Before heading there,enjoy dinner nearby,Momotarofor Japanese cuisine.
Bedtime
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4.73Rookery Building
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4.73Rookery Building
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4.84Marina City[26036]
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4.84Marina City[26036]
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Final Day Adventures
Morning
Kick off your last day visiting vibrant neighborhoods like Lincoln Park & Zoo. Start morning right with breakfast,Toast Lincoln Parkknown for brunch specialties.
Afternoon
Explore more cultural sites like{ A-Adler Planetarium[1209]}and relax in Grant Park. Lunch break nearby,{ R-The Art Institute Cafe }offering light bites.
Evening
Conclude trip experiencing Navy Pier,enjoy rides or just walk around scenic pier.Dine final night out,{ R-Riva Crab House }seafood spot on pier.
Bedtime
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