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5-Day Chicago Cultural and Culinary Adventure

5-Day Chicago Cultural and Culinary Adventure Itinerary

Last updated: 2024 Jun 14

Iconic Landmarks and River Cruises

Morning
Start your Chicago adventure with a delicious breakfast at Lou Malnati's Pizzeria, known for its deep-dish pizza. Afterward, take a stroll along the iconic Chicago Riverwalk and admire the city's architecture.
Afternoon
Enjoy a classic Chicago experience with a Chicago River 1.5-Hour Guided Architecture Cruise. For lunch, head to Giordano's for their famous stuffed pizza. After the cruise, visit the The Magnificent Mile for some upscale shopping.
Evening
Dine at The Purple Pig, offering a menu of Mediterranean-inspired small plates. End the evening with a breathtaking view from the 360 Chicago Observation Deck (Formerly John Hancock Observatory) with a Chicago 360 Chicago Observation Deck Sip and View Ticket.
Bedtime
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Chicago Riverwalk

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Chicago River 1.5-Hour Guided Architecture Cruise

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The Magnificent Mile

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360 Chicago Observation Deck (Formerly John Hancock Observatory)

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Chicago 360 Chicago Observation Deck Sip and View Ticket

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Art and Museum Day

Morning
Start your day with a gourmet brunch on a Chicago Gourmet Brunch, Lunch, or Dinner River Cruise with live jazz music. Savor the views of the city's skyline as you enjoy your meal.
Afternoon
Immerse yourself in art at the Art Institute of Chicago with a fast-pass ticket. For lunch, visit Eataly Chicago and explore the variety of Italian cuisines offered in this vibrant marketplace.
Evening
Experience the vibrant atmosphere of Millennium Park and take a selfie at the famous Cloud Gate (The Bean). Enjoy dinner at Big Star, known for its tacos and whiskey selection.
Bedtime
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Chicago Gourmet Brunch, Lunch, or Dinner River Cruise

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Art Institute of Chicago

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Millennium Park

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Family-Friendly Chicago

Morning
Take the family on a Chicago 45-Minute Family-Friendly Architecture River Cruise. Grab a quick breakfast at Portillo's Hot Dogs before boarding the cruise.
Afternoon
Explore the underwater world at the Shedd Aquarium. For lunch, head to Little Goat Diner and try their creative comfort food dishes.
Evening
Enjoy a relaxing evening at Navy Pier. Dine at Gibsons Bar & Steakhouse for a classic Chicago steakhouse experience.
Bedtime
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Chicago 45-Minute Family-Friendly Architecture River Cruise

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Shedd Aquarium

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Navy Pier

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Chicago's Culinary Scene

Morning
Start your day with a coffee and pastry at Lula Cafe, a neighborhood favorite. Then, take a guided walking tour of the Taste of Chinatown Food Walking Tour to explore the flavors of the city.
Afternoon
After the tour, visit the historic Wrigley Building and enjoy lunch at Kuma's Corner, known for its gourmet burgers. Spend the rest of the afternoon at Lincoln Park & Zoo, one of the oldest zoos in the country.
Evening
Indulge in a memorable dinner at Au Cheval, famous for its burger and upscale diner atmosphere. Afterward, take a leisurely stroll through the park or enjoy a drink at a nearby bar.
Bedtime
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Chicago Taste of Chinatown Food Walking Tour

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Wrigley Building

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Lincoln Park & Zoo

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Chicago's History and Haunts

Morning
Begin with a hearty breakfast at Smoque BBQ, known for its authentic smoked meats. Then, embark on the Chicago Gangsters and Ghosts Guided Walking Tour to uncover the city's darker history.
Afternoon
For lunch, head to Xoco and savor the flavors of Mexico in the heart of Chicago. Afterward, visit the Field Museum of Natural History or take a VIP tour to explore the world of natural science.
Evening
Conclude your trip with a visit to the Skydeck Chicago at Willis Tower (Sears Tower) and dare to step out onto The Ledge for a thrilling experience. Enjoy a farewell dinner at Alinea, a three-Michelin-star restaurant known for its innovative and artistic dishes.
Bedtime
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Chicago Gangsters and Ghosts Guided Walking Tour

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Chicago Field Museum of Natural History Ticket or VIP Tour

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Skydeck Chicago at Willis Tower (Sears Tower)

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