Chicago: Not Moving Here … Yet

I've visited Chicago several times, and, somehow, each trip feels just as special as the first. There's a familiarity to the city that makes it feel welcoming, yet I always leave having discovered a new favorite spot. This was my first solo trip to Chicago, and it completely exceeded my expectations. There’s a kind of freedom to experiencing a destination exactly how you want to, and I made the most of every minute.

Magnificent Mile covered in 1,000 tulips!

Because my flight arrived close to midnight, I spent my first night at the Hilton Chicago O'Hare, which is right inside the airport. The next morning, I took the CTA into the city and checked into Freehand Chicago, where I stayed for the rest of the trip. Freehand is a unique little place tucked into a city block that almost blends into its surroundings. The rooms and common areas are compact, but the hotel has a trendy, eclectic atmosphere and a great lounge space. I've learned that I personally prefer larger hotels with more space and a few more stars. But if you’re looking for a stylish and unconventional stay, you will likely enjoy the experience.

Iconic stop. You can't NOT go.

Coffee was a daily priority, and Chicago delivered. Blue Bottle remained my personal favorite, but I had to stop by Intelligentsia. I also found a cute little spot called Tiny Café, right along the Riverwalk. As for eating, LondonHouse Rooftop offers one of the best views in the city and is worth visiting, even if only for the scenery. River Roast was another highlight, especially for lunch downtown—the pull-apart rolls alone are worth the stop. Traveling solo also meant a healthy amount of Uber Eats, which honestly worked out perfectly between adventures.

Of course, Blue Bottle ... my first love.

LondonHouse Rooftop with the best view

One of Chicago's greatest strengths is the variety of things to do. Riverwalk. Millennium Park. The Art Institute. Lincoln Park. 360 Chicago. Oak Street Beach. Skydeck. Starbucks Reserve. Every attraction offered a different perspective of the city. My favorite experience was easily the sunset cruise. I chose Wendella Cruises, and it was the perfect way to experience Chicago's skyline and architecture. If you're deciding between a daytime or evening cruise, I strongly recommend the sunset option. Watching the city transition from daylight to dusk on the water was truly unforgettable.

Skydeck experience is worth it!

Oak Street Beach: a beautiful walk!

Chicago is an ideal destination for those who enjoy city life, walkable neighborhoods, the L (as the locals say), and the energy that comes from being surrounded by people. Despite the crowds, the city never felt overwhelming—instead, it felt vibrant, welcoming, and full of life. Whether you're planning a quick weekend getaway or a longer stay, Chicago offers more than enough experiences to fill your itinerary.

And no, I'm not moving here ... yet.

Ghirardelli with this view ...

Sunset cruise view ... nothing like it.

For more inspiration and insider recommendations, visit our Chicago page.