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.
The Fora Difference
Book with Italia to access exclusive perks and experiences on your trip.
Killer perks
Free upgrades, spa credits and more—we got you
Personalized recs
Customized travel planning for your style
Insider knowledge
Expert advice from people who’ve actually been there
Where to stay
Unlock perks by contacting Italia to book your trip.
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.
Travel Advisor
Italia Dutton
Get in touch with Italia
Did you like this guide? Reach out to customize and book your own experience. Or, just to chat about travel in general.
You can expect a response from Italia within 1–2 business days. You’ll also be subscribed to our traveler newsletter (you can unsubscribe at any time).
For more inspiration and insider recommendations, visit our Chicago page.