The Ultimate 3-Day Chicago Itinerary: Top Things to See and Do

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Advisor - Italia Dutton
Curated By

Italia Dutton

  • Chicago

  • Arts & Culture

  • Food & Wine

  • Sightseeing

  • Architecture

  • History

Advisor - The Ultimate 3-Day Chicago Itinerary: Top Things to See and Do
Curator’s statement

Welcome to the Windy City — Chicago! This vibrant metropolis, renowned for its stunning architecture, rich history and dynamic cultural scene, offers something for every kind of traveler. Whether you're a first-time visitor or returning to uncover more of its many layers, this 3-day Chicago itinerary is designed to guide you through a perfect blend of iconic landmarks, hidden gems and unforgettable experiences.

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Day 1: Arrival and architectural wonders

Begin your journey in Chicago with a visit to the iconic Willis Tower. Take in breathtaking views from the Skydeck . Afterwards, explore the architectural beauty of the Millennium Park and don't miss the famous Cloud Gate. Check into your hotel, The Langham, Chicago, and unwind with their exquisite amenities. For dinner, indulge in a culinary experience at Gibsons Bar & Steakhouse.

Day 2: Art and culture immersion

Dive into the world of art at the Art Institute of Chicago, home to a vast collection of artworks. Have breakfast/brunch at Wildberry Pancakes and Cafe before you spend your afternoon at River North, known for its vibrant art galleries and chic boutiques. Enjoy lunch at Quartino Ristorante & Wine Bar. In the evening, catch a show at the historic Chicago Theatre for a taste of the city's cultural scene.

Day 3: Nature and neighborhoods

Start your day with a leisurely stroll through Lincoln Park Zoo, one of the oldest zoos in the country. Explore the surrounding Lincoln Park area, known for its charming streets and cafes. Have brunch at The Bongo Room. In the afternoon, relax at the North Avenue Beach or take a scenic walk along the Lakefront Trail. Conclude your trip with dinner at Lou Malnati's Pizzeria, a must-try for authentic Chicago-style pizza.

Let me know if you need any more details or adjustments for your trip!

Need to know

This itinerary offers a perfect mix of Chicago’s must-see attractions and local treasures, ensuring a memorable and well-rounded experience.

Advisor - Italia Dutton

Travel Advisor

Italia Dutton

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