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Chicago Architecture, Comedy, and Deep Dish Delights Itinerary
Last updated: 2024 Jun 14Iconic Chicago Landmarks and Deep Dish Indulgence
Morning
Start your Chicago experience with a visit to the famous The Magnificent Mile. Afterward, take a leisurely walk to the historic Wrigley Building and enjoy the architecture.
Afternoon
For lunch, savor the city's best deep dish pizza at Lou Malnati's Pizzeria. Afterward, head to Millennium Park to see the iconic Cloud Gate sculpture, also known as "The Bean."
Evening
In the evening, enjoy a hilarious show at The Second City, a renowned comedy club that has launched many famous comedians. Conclude the day with a delightful dessert at The Purple Pig.
Bedtime
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4.65The Magnificent Mile
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4.65The Magnificent Mile
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4.39Wrigley Building
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4.39Wrigley Building
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Architectural Marvels and River Cruises
Morning
Begin your day with a visit to the Art Institute of Chicago, home to a world-class collection of art.
Afternoon
For lunch, experience a variety of gourmet options at Eataly Chicago. Afterward, take the Chicago River 1.5-Hour Guided Architecture Cruise to admire the city's skyline.
Evening
Enjoy a sophisticated dinner at The Signature Room at the 95th, offering stunning views of the city. After dinner, take a leisurely walk along the Chicago Riverwalk.
Bedtime
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4.61Art Institute of Chicago
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4.61Art Institute of Chicago
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4.77Chicago River 1.5-Hour Guided Architecture Cruise
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4.77Chicago River 1.5-Hour Guided Architecture Cruise
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Exploring Cultural Gems and Culinary Delights
Morning
Visit the Field Museum to explore natural history and cultural exhibits.
Afternoon
For a late lunch, enjoy the vibrant atmosphere and Mediterranean flavors at The Publican. Afterward, take a relaxing Chicago Lake Michigan Skyline Cruise.
Evening
Indulge in a unique dining experience at Alinea, a three-Michelin-star restaurant. After dinner, take a stroll through the lively neighborhood of Lincoln Park & Zoo.
Bedtime
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4.56Field Museum
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4.56Field Museum
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4.59Chicago Lake Michigan Skyline Cruise
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4.59Chicago Lake Michigan Skyline Cruise
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Gangsters, Ghosts, and Local Brews
Morning
Embark on the Chicago Discover the Gangsters & Ghosts of the City's Past tour to learn about the city's darker history.
Afternoon
For a casual lunch, try the famous tacos at Big Star. Afterward, visit the 360 Chicago Observation Deck (Formerly John Hancock Observatory) for panoramic views.
Evening
Enjoy a relaxed dinner at Pequod's Pizza, known for its caramelized crust. Then, experience the local brewery scene with a visit to Goose Island Brewery.
Bedtime
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4.68Chicago Discover the Gangsters & Ghosts of the City's Past
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4.68Chicago Discover the Gangsters & Ghosts of the City's Past
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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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Final Taste of Chicago's Culinary Scene
Morning
Spend your last morning in Chicago exploring the Chicago Cultural Center, a historic building with stunning architecture.
Afternoon
For a memorable final meal, indulge in a gourmet experience at Girl & the Goat, known for its creative dishes. Afterward, take a relaxing walk along the Chicago Riverwalk.
Evening
Conclude your trip with a visit to a local comedy club for a night of laughter and entertainment.
Bedtime
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4.71Chicago Cultural Center
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4.71Chicago Cultural Center
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4.72Chicago Riverwalk
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4.72Chicago Riverwalk
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