Where the Skyline Meets the Shore: My Love Letter to Chicago

Lake Michigan

One of Chicago’s biggest highlights is its setting along Lake Michigan. In warmer months, the lakefront trail is perfect for walking or biking, and the beaches feel like a summer escape without leaving the city. Even in colder months, the views alone are worth bundling up for.

The neighborhoods

Chicago is a city of neighborhoods, each with its own personality. Downtown (The Loop) is where you’ll find iconic architecture, river views, and easy access to Millennium Park and the Art Institute. Head north to River North and Gold Coast for upscale hotels, rooftop bars, and shopping along the Magnificent Mile—including the immersive Harry Potter Shop Chicago, where fans can browse themed merchandise and stop at the in-store café for a frozen or classic butterbeer. Venture west to the West Loop for some of the city’s best restaurants, or south for rich cultural history and incredible music roots. A river architecture cruise is one of the best introductions to the city—even locals love it.

Griffin Museum of Science and Industry

While exploring Chicago, I highly recommend carving out time for the Griffin Museum of Science and Industry. It’s one of those places that surprises you with how immersive it is—not just for kids, but for genuinely curious adults too. The absolute highlight is the U-505 Submarine experience.

For an additional ticket, you can take a guided tour inside the real captured German U-boat from World War II. Walking through the tight corridors and engine rooms makes history feel incredibly tangible, and it’s well worth the extra cost if you enjoy interactive experiences.

Food

If you’re a foodie (or just love exploring neighborhoods with a strong cultural identity), Chicago’s Chinatown is a must. The area is packed with incredible restaurants representing different regions of China—from hand-pulled noodles and Szechuan spice, to Cantonese barbecue and dim sum. It’s easy to spend an entire afternoon hopping between bakeries, tea shops, and full-service restaurants.

Ghost tours

For travelers who enjoy a slightly different kind of evening activity, Chicago also offers a variety of ghost tours. One of the most intriguing focuses on H. H. Holmes and the infamous “Murder Castle” tied to the World's Columbian Exposition. These tours dive into the darker side of Chicago’s history and are typically offered during the spring and summer months (some are available in winter). It’s a fascinating way to experience the city after dark and adds an unexpected layer to Chicago’s already rich story.

Chicago is one of those cities where you can eat something iconic one minute and completely unexpected the next. Here are my personal favorites from this trip and beyond.

• Chinatown Food Tour: If you want to try dishes from multiple regions of China in one afternoon, this is the move. It’s the best way to explore beyond just one restaurant and really understand the diversity of Chinese cuisine—come hungry.

• Tony’s Garage Dinner Show: Dinner and entertainment in one night. It’s quirky, interactive, and perfect if you want something a little different than just sitting at a restaurant. Great for groups or a fun date night.

• Giordano's: You can’t come to Chicago and not try deep-dish at least once. Giordano’s is a classic—plan ahead because these pies take time, but they’re worth it.

• The Tavern at Thompson Chicago: Attached to Thompson Chicago, this is such a convenient and genuinely good spot. Great service, solid cocktails, and an easy place to use a property credit if you have one.

• Café on Oak (inside The Drake): Perfect for a slower morning. It’s cozy and classic Chicago—ideal for coffee and a light breakfast before heading out to explore.

• Afternoon Tea at The Drake Hotel: If you want something a little elevated and iconic, tea at The Drake is such a fun experience. Think tradition, lake views, and a great excuse to dress up a little.

• Yolk: One of my favorite breakfast/brunch spots. Big portions, lots of options, and exactly what you need before a full day of walking the city.

• Portillo's: For a quick, casual Chicago staple—this is it. Italian beef, hot dogs, and chocolate cake shakes. No frills, just iconic comfort food.

Chicago truly lets you mix classic, cultural, and completely unexpected all in one weekend—and that’s what makes the food scene so fun to explore.