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3-Day Chicago City Explorer Itinerary

3-Day Chicago City Explorer Itinerary Itinerary

Published: 2023 Dec 31

Iconic Landmarks and Sky-high Views

Morning
Start your Chicago adventure with a delightful breakfast at Cindy's Rooftop, offering stunning views of the city. Afterward, head to the historic Wrigley Building and take a leisurely walk along the Chicago Riverwalk to admire the architectural marvels.
Afternoon
For lunch, indulge in the vibrant atmosphere and gastropub cuisine at The Gage. Post-lunch, experience the city from the 360 Chicago Observation Deck with your skip-the-line ticket. Enjoy the breathtaking panoramic views and even try the "Sip and View" option for a drink with a view.
Evening
Dine at The Franklin Room, known for its speakeasy ambiance and craft cocktails. Afterward, take a relaxing Chicago River 1.5-Hour Guided Architecture Cruise to witness the city's famous skyline and learn about its rich history.
Bedtime
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Museums, Parks, and Cultural Delights

Morning
Fuel up for the day with a hearty breakfast at State and Lake Chicago Tavern. Then, spend your morning exploring the vast collections of the Art Institute of Chicago with your fast-pass ticket. Don't miss the iconic "Bean" at Millennium Park nearby.
Afternoon
Enjoy a leisurely lunch at The Dearborn, offering a modern take on classic American fare. Post-lunch, immerse yourself in the wonders of science and industry at the Chicago Museum of Science and Industry with your included ticket.
Evening
As the day winds down, take a relaxing stroll through the serene Grant Park, also known as "Chicago's front yard." For dinner, savor the flavors of the city at Sweetwater Tavern & Grille (Michigan Plaza - Chicago).
Bedtime
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Neighborhoods, Zoos, and Evening Entertainment

Morning
Begin your day with breakfast at Plymouth Restaurant & Rooftop Bar, offering a great start with a view. Then, head to the lively Navy Pier and enjoy the morning exploring the attractions, including a ride on the Centennial Wheel with your express ticket.
Afternoon
For lunch, visit Old Town Pour House (Old Town - Chicago) and enjoy a wide selection of craft beers and elevated pub food. Afterward, take a trip to the Lincoln Park Zoo, one of the oldest zoos in the country, and spend a delightful afternoon with the animals.
Evening
Conclude your Chicago journey with a memorable dinner at FireLake Grill House and Cocktail Bar, known for its warm hospitality and regional flavors. Afterward, if you're up for some entertainment, consider the vibrant shows at House of Blues Restaurant & Bar.
Bedtime
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Adjacent Cities

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