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Ultimate Chicago Experience: Architecture, Food, and Culture Itinerary
Last updated: 2024 Jun 14Iconic Chicago Landmarks and Skyline Views
Morning
Start your day with a classic Chicago breakfast at Lou Mitchell's, known for its hearty omelets and pancakes. After breakfast, take a stroll through the iconic Millennium Park and marvel at the famous "Bean" sculpture.
Afternoon
For lunch, enjoy a deep-dish pizza at Lou Malnati's Pizzeria, a Chicago staple. Afterward, visit the Art Institute of Chicago and explore its world-class art collection.
Evening
In the evening, head to the 360 Chicago Observation Deck (Formerly John Hancock Observatory) for panoramic views of the city at sunset. Then, have a memorable dinner at The Signature Room at the 95th, where you can enjoy fine dining with a view.
Bedtime
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4.69Millennium Park
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4.69Millennium Park
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4.61Art Institute of Chicago
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4.61Art Institute of Chicago
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Gangsters, Ghosts, and Culinary Delights
Morning
Start your day with a delicious brunch at Lula Cafe in the vibrant Logan Square neighborhood. Afterward, embark on the Chicago Mob and Crime Bus Tour to learn about the city's notorious past.
Afternoon
For a unique experience, take the Chicago Food, History and Architecture Tour, where you can sample a variety of local dishes while exploring the city. After the tour, visit the Chicago Cultural Center.
Evening
Enjoy a spooky evening on the Chicago Gangsters and Food Tasting Walking Tour, combining history with delicious food. End the night with a drink at Violet Hour, a speakeasy-style bar.
Bedtime
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4.39Chicago Mob and Crime Bus Tour
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4.39Chicago Mob and Crime Bus Tour
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4.84Chicago Food, History and Architecture Tour
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4.84Chicago Food, History and Architecture Tour
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Architectural Marvels and Culinary Adventures
Morning
Start your day with a pastry and coffee at Floriole Cafe & Bakery in Lincoln Park. Then, take the Chicago Architecture Center Cruise on Chicago's First Lady to learn about the city's stunning architecture.
Afternoon
For lunch, savor the flavors of Mexico at Rick Bayless' Frontera Grill. Afterward, visit the 360 Chicago Observation Deck (Formerly John Hancock Observatory) for a different perspective of the city.
Evening
Indulge in a fine dining experience at Alinea, one of Chicago's most renowned restaurants. After dinner, take a leisurely walk along the Chicago Riverwalk.
Bedtime
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4.46Chicago Architecture Center Cruise on Chicago's First Lady
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4.46Chicago Architecture Center Cruise on Chicago's First Lady
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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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Museums, Science, and Skyline Cruises
Morning
Enjoy a hearty breakfast at Wildberry Pancakes and Cafe before heading to the Field Museum to explore natural history and culture.
Afternoon
For lunch, try the famous pastrami sandwich at Manny's Cafeteria & Delicatessen. Afterward, visit the Willis Tower Skydeck and The Ledge for thrilling views of the city.
Evening
Relax on a Chicago Lake Michigan Buffet Brunch, Lunch or Dinner Cruise, enjoying a meal with a view of the skyline. After the cruise, take a walk around the Navy Pier.
Bedtime
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4.56Field Museum
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4.56Field Museum
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4.41Willis Tower Skydeck and The Ledge
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4.41Willis Tower Skydeck and The Ledge
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Final Taste of Chicago
Morning
For your last morning in Chicago, have a leisurely breakfast at Yolk, known for its creative egg dishes. Then, take a walk through the historic Wrigley Field.
Afternoon
Spend your final afternoon at the Adler Planetarium and Shedd Aquarium, immersing yourself in the wonders of the universe and the sea. For a late lunch, enjoy the views at Cindy's.
Evening
End your Chicago adventure with a dinner at Girl & the Goat, a favorite for its innovative cuisine. After dinner, take a Chicago River Guided Sunset Cocktail & Architecture Tour to see the city lights come alive.
Bedtime
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4.86Wrigley Field
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4.86Wrigley Field
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4.61Adler Planetarium
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4.61Adler Planetarium
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