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5 Days Exploring Chicago Itinerary
Last updated: 2024 Jun 14Welcome to the Windy City
Morning
Start your day with a visit to the iconic Millennium Park, where you can see the famous Cloud Gate sculpture. Enjoy a coffee at The Goddess and Grocer, known for its delicious pastries and coffee.
Afternoon
Head over to the Art Institute of Chicago to explore its vast collection of art. For lunch, dine at The Gage, a popular spot known for its upscale pub fare.
Evening
In the evening, catch a show at the historic Chicago Theatre. Before the show, enjoy dinner at RPM Italian, which offers modern Italian cuisine.
Bedtime
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Millennium Park
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Art Institute of Chicago
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Chicago Theatre
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Architectural Marvels and Sports
Morning
Begin your day with a visit to the stunning Rookery Building, an architectural masterpiece. Grab breakfast at Lou Mitchell's, a classic Chicago diner.
Afternoon
Take a tour of the legendary Wrigley Field, home of the Chicago Cubs. Have lunch nearby at Sheffield's Beer & Wine Garden, known for its BBQ and craft beers.
Evening
Spend your evening enjoying live music at the famous House of Blues. Dine beforehand at Girl & The Goat, one of Chicago's most celebrated restaurants.
Bedtime
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Rookery Building
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Wrigley Field
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House of Blues
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Museums and Lakefront Views
Morning
Visit the fascinating exhibits at the Field Museum. Start your day with breakfast at Yolk South Loop, which offers hearty breakfast options.
Afternoon
Explore marine life at the nearby Shedd Aquarium. For lunch, head to Pierrot Gourmet for some French-inspired dishes.
Evening
Take an evening stroll along the scenic Chicago Riverwalk. Enjoy dinner with river views at City Winery Chicago Riverwalk.
Bedtime
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Field Museum
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Shedd Aquarium
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Chicago Riverwalk
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Parks and Planetarium
Morning
Start your day with a relaxing walk in Grant Park. Have breakfast at Wildberry Pancakes and Cafe, famous for its pancakes.
Afternoon
Visit the stars at the impressive Adler Planetarium. Enjoy lunch nearby at The Dock at Montrose Beach with beautiful lake views.
Evening
Catch a comedy show in Old Town's renowned venue, Second City. Before that, have dinner at Twin Anchors Restaurant & Tavern known for its ribs.
Bedtime
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Grant Park
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Adler Planetarium
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Second City
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Shopping and Farewell
Morning
Spend your morning shopping along The Magnificent Mile . Grab breakfast or brunch from The Purple Pig known for its Mediterranean-inspired dishes.
Afternoon
Explore more of Chicago’s architecture by visiting Marina City and then have lunch nearby in Eataly Chicago which offers various Italian delicacies.
Evening
End your trip with an evening visit to Navy Pier where you can enjoy various attractions. Have dinner on-site in Offshore Rooftop & Bar which provides great views of Lake Michigan.
Bedtime
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The Magnificent Mile
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Marina City
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Navy Pier
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Adjacent Cities
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