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Ultimate 4-Day Chicago Adventure with Top Attractions and Dining

Ultimate 4-Day Chicago Adventure with Top Attractions and Dining Itinerary

Last updated: 2024 Jun 14

Iconic Landmarks and River Cruises

Morning
Begin your Chicago adventure with a delightful breakfast at Lou Malnati's Pizzeria, known for its famous deep-dish pizza. Afterward, take a stroll along the Chicago Riverwalk to enjoy the morning views of the city's architecture.
Afternoon
Immerse yourself in the city's history and skyline on the Chicago River 1.5-Hour Guided Architecture Cruise. For lunch, hop off at Navy Pier and savor the flavors of Big Star, offering a menu of creative tacos and cocktails.
Evening
Experience the breathtaking heights of the city at the 360 Chicago Observation Deck, and enjoy a drink with a view with the Sip and View Ticket. For dinner, indulge in the elegant ambiance and exquisite dishes at The Signature Room at the 95th.
Bedtime
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Chicago Riverwalk

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Chicago River 1.5-Hour Guided Architecture Cruise

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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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Museums and Scenic Views

Morning
Fuel up for the day with a hearty breakfast at The Purple Pig, offering a menu of Mediterranean flavors. Then, head to the Art Institute of Chicago to explore one of the oldest and largest art museums in the US.
Afternoon
After the museum, enjoy a leisurely lunch at Eataly Chicago, an Italian marketplace with various dining options. Spend your afternoon at the 360 Chicago Observation Deck (Formerly John Hancock Observatory), where you can also take part in the thrilling Tilt Experience.
Evening
For dinner, embrace the vibrant atmosphere and bold flavors at Girl & the Goat. End your evening with a relaxing walk at Millennium Park, admiring the famous "Bean" sculpture and the park's stunning architecture.
Bedtime
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Art Institute of Chicago

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360 Chicago Observation Deck (Formerly John Hancock Observatory)

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Millennium Park

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Cultural Explorations and Gourmet Delights

Morning
Start with a breakfast at Lula Cafe, a neighborhood spot known for its creative dishes. Then, take a walk through the Wrigley Building and the Tribune Tower to appreciate the city's architectural history.
Afternoon
For lunch, enjoy the casual and cozy ambiance of Little Goat Diner, with a menu of classic comfort foods. Spend your afternoon at the Field Museum, exploring the natural history and cultural exhibits.
Evening
Dine at Au Cheval, famous for its mouthwatering burgers and a selection of craft beers. After dinner, take a Chicago Gangsters and Ghosts Guided Walking Tour to uncover the city's mysterious and dark past.
Bedtime
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Wrigley Building

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Tribune Tower

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Field Museum

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Chicago Gangsters and Ghosts Guided Walking Tour

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Culinary Tour and Evening Entertainment

Morning
Embark on a gastronomic journey with the Taste of Chinatown Food Walking Tour. Sample a variety of Chinese delicacies and learn about the neighborhood's rich history. For a quick bite, grab a snack at Portillo's Hot Dogs, a Chicago classic known for its hot dogs and Italian beef sandwiches.
Afternoon
Enjoy the rest of your afternoon at the Lincoln Park Zoo, one of the oldest zoos in the US, and the nearby Lincoln Park for a leisurely stroll. For a sweet treat, visit the Museum of Science and Industry and indulge in the interactive exhibits.
Evening
Conclude your Chicago journey with a memorable dinner at Gibsons Bar & Steakhouse, offering prime steaks and an extensive wine list. Afterward, you can catch a live performance at the historic Chicago Theatre or enjoy the vibrant nightlife of the city.
Bedtime
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Chicago Taste of Chinatown Food Walking Tour

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Lincoln Park & Zoo

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Lincoln Park & Zoo

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Museum of Science and Industry

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Chicago Theatre

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