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Ultimate 3-Week Chicago Exploration with Top Attractions & Dining

Ultimate 3-Week Chicago Exploration with Top Attractions & Dining Itinerary

Last updated: 2024 Jun 14

Iconic Chicago Landmarks and Deep Dish Delight

Morning
Start your Chicago adventure with a visit to the famous The Magnificent Mile, where you can enjoy some morning shopping and marvel at the city's architecture.
Afternoon
For lunch, savor the iconic deep-dish pizza at Lou Malnati's Pizzeria, a must-try in Chicago. Afterward, take a leisurely walk to The Art Institute of Chicago and immerse yourself in world-class art.
Evening
In the evening, head to Millennium Park to see the famous "Bean" and enjoy a relaxing stroll in the park. For dinner, indulge in a gourmet experience at Alinea, one of the city's top restaurants.
Bedtime
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Visit The Magnificent Mile in Chicago
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The Magnificent Mile

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Visit Art Institute of Chicago in Chicago
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The Art Institute of Chicago

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Lakefront Serenity and Sky-High Views

Morning
Enjoy a peaceful morning at Lake Michigan, take a walk along the lakefront, and soak in the beautiful views.
Afternoon
For lunch, try the delicious barbecue at Smoque BBQ. Afterward, visit the 360 Chicago Observation Deck for panoramic views of the city.
Evening
Have a memorable dinner at The Signature Room at the 95th, where you can enjoy both great food and a stunning view of the city.
Bedtime
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Visit Chicago 360 Chicago Observation Deck General Admission in Chicago
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360 Chicago Observation Deck

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Museum Day and River Cruise

Morning
Spend your morning exploring the Field Museum and learning about natural history and culture.
Afternoon
For lunch, have a taste of Italy at Eataly Chicago. Afterward, take the Chicago Architecture Center Cruise on Chicago's First Lady to admire the city's skyline.
Evening
Enjoy a relaxing evening with a dinner cruise on the Chicago River with gourmet food and beautiful views.
Bedtime
Find amazing hotels in Chicago.
Visit Field Museum in Chicago
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Field Museum

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Visit Chicago Architecture Center Cruise on Chicago's First Lady in Chicago
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Chicago Architecture Center Cruise on Chicago's First Lady

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Adjacent Cities

IndianapolisLouisvilleNashvilleMemphisDallasAustinHouston

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