3 Days in Chicago: Our Family Itinerary
Chicago quickly became one of our favorite U.S. cities — full of culture, architecture, fun attractions, and delicious food. Whether you’re visiting for a long weekend or a short city break, three days are enough to experience its highlights.
In this post, we’re sharing our 3-day Chicago itinerary — everything we did, where we ate, and what we loved most, based on our own trip from Barcelona to Chicago.
✈️ Day 1 – Arrival and Downtown Discoveries
Our Chicago adventure began when we flew from Barcelona to Chicago with United Airlines, experiencing their Basic Economy class firsthand.
👉 Read our detailed review here.
After landing and checking into our hotel, we decided to start our trip with one of the city’s most famous attractions — Skydeck Chicago at Willis Tower.
Standing on the glass ledge, 1,353 feet above the ground, was a breathtaking and slightly nerve-wracking experience! The views stretch across the entire city and even into neighboring states on a clear day.
👉 See our Skydeck Chicago experience.
Afterwards, we took a relaxing stroll along Michigan Avenue, admiring the mix of historic and modern buildings. In the evening, we stopped at Grant Park and the Buckingham Fountain, right across from where we were staying.
Watching the illuminated fountain at night, with the skyline in the background, was the perfect way to wrap up our first evening in Chicago.
👉 Read about Grant Park and the Buckingham Fountain.
☕ Day 2 – Architecture, Breakfast, and Sky-High Views
We started our second day at the Nutella Café on Michigan Avenue — a must-visit for anyone with a sweet tooth! From Nutella waffles to crepes and coffee, breakfast was simply delicious, though there was a small queue to get in.
👉 Our full Nutella Café review.
After breakfast, we headed to Millennium Park to see the Bean (Cloud Gate) — one of Chicago’s most iconic landmarks. Before entering the park, we passed through a quick security check, and once inside, we were amazed by the mirror-like sculpture reflecting the entire city.
👉 Our experience at Millennium Park and Cloud Gate.
Next, we used our CityPASS C3 to visit 360 Chicago, located in the John Hancock Center. It was our third attraction with the pass, after Skydeck and the Architecture Tour.
The views from the 94th floor were breathtaking — but we learned that the Tilt experience is not included with CityPASS and costs an extra $18 per person. If you buy tickets directly, you can even combine the Tilt with a drink.
👉 More about our 360 Chicago experience.
For lunch, we went straight to Giordano’s, the home of Chicago’s legendary deep-dish pizza. The pizza was everything we hoped for — cheesy, rich, and perfectly baked.
👉 Our Giordano’s experience.
In the evening, we walked to Navy Pier, our final stop for the day. This lively spot by Lake Michigan is filled with restaurants, shops, and attractions, including the famous Ferris Wheel. It was the perfect way to end our second day with city lights and lakeside views.
👉 Read more about Navy Pier.
🐧 Day 3 – Family Fun and Zoo Adventure
On our last day in Chicago before heading to Milwaukee, we spent the morning at Lincoln Park Zoo — one of the oldest and only free zoos in the United States.
It’s a fantastic place for families, home to lions, penguins, giraffes, and so many more animals. The zoo’s Nature Boardwalk offers one of the best skyline views in the city, surrounded by trees and water.
👉 Read our Lincoln Park Zoo experience.
Before leaving, we enjoyed a final Chicago coffee stop at the Starbucks Reserve Roastery, the largest Starbucks in the world. Spread across five floors, each level offers a unique experience — from fresh pastries to a cocktail bar.
👉 Full guide to the Starbucks Reserve Roastery Chicago.
This was the perfect finale to our three-day Chicago adventure — a trip full of iconic sights, unique food, and unforgettable family memories.
🛥️ Bonus: Don’t Miss the Shoreline Architecture Tour
One of our favorite Chicago experiences was the Shoreline Sightseeing Architecture Tour, which we took earlier during our stay. Cruising down the Chicago River while learning about the city’s famous buildings gave us a new perspective on its incredible skyline.
👉 Our full architecture tour experience.
🌇 Our Chicago Takeaway
Chicago truly offers something for everyone — families, couples, architecture lovers, and foodies alike. Three days felt short but unforgettable. Between skyscrapers and parks, we discovered a city that perfectly balances urban energy and natural beauty.
If you’re planning your own 3-day Chicago itinerary, we highly recommend combining Skydeck, Millennium Park, 360 Chicago, and Lincoln Park Zoo, with delicious meals at Nutella Café and Giordano’s.
Frequently Asked Questions about 3 Days in Chicago
Is 3 days enough to see Chicago?
Yes! Three days are enough to explore Chicago’s main attractions including Skydeck, Millennium Park, 360 Chicago, and Navy Pier.
What’s the best way to get around Chicago?
The city is easy to explore on foot or by using public transport and rideshare apps. CityPASS C3 is great for attraction savings.
What are must-visit attractions in Chicago?
Top attractions include Skydeck Chicago, The Bean, 360 Chicago, Grant Park, Navy Pier, and the Lincoln Park Zoo.
Where to eat in Chicago?
Don’t miss Giordano’s for deep-dish pizza and Nutella Café for a sweet breakfast on Michigan Avenue.
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