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5 Days in Chicago Midwest Winter Getaway Itinerary
Last updated: 2024 Jun 14Exploring the Loop and Beyond
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. Afterward, grab a coffee and breakfast at Wildberry Pancakes and Cafe.
Afternoon
Head over to Millennium Park to see the famous Cloud Gate sculpture (The Bean) and enjoy a leisurely walk through this urban oasis. For lunch, stop by Girl & The Goat, known for its innovative dishes.
Evening
In the evening, explore Chicago Riverwalk, which offers stunning views of the city skyline. End your day with dinner at Alinea, a three-Michelin-starred restaurant offering an unforgettable dining experience.
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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4.69Millennium Park
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4.69Millennium Park
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Cultural Gems and Architectural Wonders
Morning
Begin your day with a visit to the Art Institute of Chicago, home to an extensive collection of art from around the world. Enjoy breakfast at The Bongo Room, known for its creative brunch dishes.
Afternoon
Afterward, take a stroll through Grant Park and visit Grant Park. For lunch, head to Portillo's Hot Dogs for a taste of classic Chicago-style hot dogs.
Evening
In the evening, catch a show at the historic Chicago Theatre. For dinner, dine at Gibsons Bar & Steakhouse, renowned for its steaks and vibrant atmosphere.
Bedtime
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4.61Art Institute of Chicago
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4.61Art Institute of Chicago
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4.70Grant Park
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4.70Grant Park
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Aquatic Adventures and Sporting Excitement
Morning
Start your day with a visit to the fascinating Shedd Aquarium, where you can explore marine life from around the globe. Have breakfast at Yolk - South Loop for hearty morning fare.
Afternoon
Next, head over to Soldier Field for a tour of this historic stadium. Grab lunch nearby at The Gage, which offers upscale pub food in an elegant setting.
Evening
In the evening, experience live music at House of Blues. Enjoy dinner beforehand at RPM Italian for delicious Italian cuisine.
Bedtime
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4.75Shedd Aquarium
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4.75Shedd Aquarium
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5.00House of Blues
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5.00House of Blues
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Science and Skyline Views
Morning
Visit the renowned Museum of Science and Industry in Hyde Park. Start your morning with breakfast at Valois Restaurant nearby.
Afternoon
After exploring the museum's interactive exhibits, take some time to relax at Jackson Park. For lunch, try Medici on 57th Street for eclectic American eats.
Evening
End your day with stunning views from 360 Chicago Observation Deck (Formerly John Hancock Observatory). Have dinner at The Signature Room on 95th for fine dining with panoramic views.
Bedtime
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4.31Museum of Science and Industry
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4.31Museum of Science and Industry
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4.17360 Chicago Observation Deck (Formerly John Hancock Observatory)
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4.17360 Chicago Observation Deck (Formerly John Hancock Observatory)
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Historic Highlights and Farewell Chicago
Morning
Begin your final day with a visit to Lincoln Park & Zoo. Enjoy breakfast nearby at Batter & Berries known for their inventive dishes.
Afternoon
Explore more history by visiting Marina City followed by lunch at Lou Malnati's Pizzeria for some deep-dish pizza goodness.
Evening
'Conclude your trip by visiting Wrigley Field followed by dinner at Joe's Seafood Prime Steak & Stone Crab.'
Bedtime
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