A First-Timer’s Guide to Chicago: Where to Go and What to Do
Welcome to the Windy City!
Chicago has a way of pulling you in. Maybe it’s the towering skyscrapers lining the Chicago River, or the aroma of deep-dish pizza wafting through the streets. Perhaps it’s the lakefront that stretches for miles, offering a peaceful contrast to the hustle and bustle of the city. Whatever the draw, one thing is certain—if it’s your first time in Chicago, you’re in for an experience that will stick with you long after you leave.
I’ve visited Chicago a couple of times, and each trip has given me a different perspective on the city. Whether you’re here for a weekend getaway or a longer stay, you’ll quickly find that there’s something for everyone, from breathtaking skyline views to world-class museums, historic neighborhoods, and an ever-evolving food scene. To help you make the most of your visit, here’s what I recommend for first-time visitors.
🏙️ Skydeck vs. 360 CHICAGO – Which View is Best?
If you want a bird’s-eye view of the city, you have two main choices: Skydeck Chicago at Willis Tower or 360 CHICAGO at the former John Hancock Center. Both offer panoramic views of the city, but they provide very different experiences.
📌 Skydeck Chicago (Willis Tower)
The highest observation deck in Chicago at 1,353 feet (412 meters).
Features The Ledge, a series of glass boxes extending out from the building, giving you the feeling of standing in mid-air.
Best for: Thrill-seekers who want to test their nerves while enjoying breathtaking city views.
📌 360 CHICAGO (John Hancock Center)
Stands at 1,030 feet (314 meters) with incredible views of Lake Michigan and the city skyline.
Features TILT, a thrill ride that leans visitors forward over the edge of the building.
Home to CloudBar, where you can sip a cocktail while taking in the sights.
Best for: A more relaxed, less crowded experience with stunning views over the lake.
💡 My Recommendation: If you’re looking for a quieter, more comfortable experience with amazing views, 360 CHICAGO is your best bet. It tends to be less crowded, and you can stay as long as you like.
🎭 Must-See Attractions
No trip to Chicago is complete without checking out a few of its iconic landmarks. Here are some must-see spots that first-time visitors won’t want to miss:
📌 Millennium Park & Cloud Gate (a.k.a. The Bean)
You simply have to get the classic photo at Cloud Gate, one of Chicago’s most famous landmarks.
Millennium Park is perfect for people-watching, free concerts, and public art.
💡 Pro Tip: Visit in the morning or late afternoon to avoid crowds.
📌 The Field Museum & The Art Institute of Chicago
If you love history and science, The Field Museum is home to Sue the T-Rex, one of the most complete T-Rex skeletons ever found.
The Art Institute of Chicago houses famous works, including American Gothic and A Sunday Afternoon on the Island of La Grande Jatte.
💡 Why Visit? These museums are fantastic for homeschooling families or travelers looking for a cultural, self-paced experience.
📌 Chicago River Dinner Cruise
One of the best ways to enjoy the city at night is by booking a dinner cruise on the Chicago River.
You’ll get stunning views of the illuminated skyline while enjoying a great meal.
💡 Pro Tip: Book in advance, especially during peak travel months.
🛤️ Are You Ready to Go to Chicago Now?
Chicago is one of those cities that blends history, architecture, food, and culture seamlessly. Whether you’re walking along the lakefront, taking in the skyline from above, or snapping a selfie at The Bean, there’s something unforgettable around every corner.
Have you been to Chicago?
What’s at the top of your must-see list?
Let me know in the comments!
🍽️ Where to Eat (Coming in a Future Post!)
Chicago is one of the best food cities in the U.S. Whether you’re craving deep-dish pizza, Chicago-style hot dogs, or an upscale steakhouse experience, there’s something for every palate. I’ll be covering the must-try foods and restaurants in a separate post, so stay tuned!
💡 What’s Next in the Series?
There’s so much more to see in Chicago, so stay tuned for upcoming guides covering:
✅ Best Places to Eat in Chicago 🍕
✅ Navy Pier & Lakefront Activities 🌊
✅ Chicago Sports & Game Day Experiences ⚾🏀
✅ Hop-On Hop-Off Tours – Worth It? 🚌
