Under the Chicago Skyline!
Updated: Jun 26
One of the most beautiful downtown cities I’ve visited in the U.S., Chicago completely exceeded my expectations. It reminded me of a mix of London, Paris, and New York, while still maintaining its own distinct Chicago vibe. It’s a big city with its pros and cons, but we mostly stayed around the Loop and nearby areas and felt as safe as in any other major, bustling city.
Arrival day: riverwalk views and a memorable first stop
We kicked off the trip with a visit to the massive Starbucks Reserve Roastery, the largest Starbucks. Even with all that space, it was extremely busy, with lines stretching across multiple floors and a few items already sold out. The menu felt completely different from a regular Starbucks, with specialty items you won’t find at typical locations, and the space itself was an experience. It’s definitely one of those “try it once” Chicago spots.
We stayed at the Sheraton Grand Chicago Riverwalk, which ended up being an amazing choice. The location was one of the highlights, right by the river with beautiful views and easy access to everything.
After arriving, we kept things relaxed and spent the evening unwinding along the riverwalk, which was the perfect way to ease into the trip.
First full day: classic Chicago views
Our first full day was all about exploring downtown. We visited Millennium Park, saw The Bean, and walked through Maggie Daley Park while taking in the skyline.
Chicago really knows how to show off its architecture, even just walking around felt like an experience in itself.
We also made our way to Navy Pier and rode the Centennial Wheel, Chicago’s iconic Ferris wheel. It was a long holiday weekend, so the city felt packed everywhere, but the energy made it fun rather than overwhelming. The views from the wheel were amazing. The Flyover experience was sold out, but we’ve done similar attractions elsewhere, so we didn’t feel like we missed out too much.
Later, we stopped by the Museum of Ice Cream, which added a playful and colorful break to the day. Even though we had prebooked, there was still a long line to enter because of the holiday crowds.
Next day: unique experiences and a must-do activity
We started with Color Factory, which was fun and interactive. We’ve actually done it in a few other cities too, but the kids make sure we visit every time. After that, we did the architecture boat tour, which was easily one of the highlights of the entire trip.
We went with Shoreline Sightseeing near the riverwalk, and seeing Chicago from the water gave such a different perspective. The skyline looks incredible from there, and I’d absolutely recommend this as a top experience for anyone visiting Chicago for the first time. The weather that day was also perfect, cool, comfortable, and ideal for walking around.
Next day: skyline views from above
We visited both Skydeck Chicago and 360 CHICAGO, and I’m really glad we experienced both—they offer different perspectives of the city.
If I had to choose just one, I’d go with Skydeck Chicago for The Ledge, since it feels like the classic, bucket-list Chicago experience. That said, 360 CHICAGO also offers equally stunning views and has a more relaxed atmosphere overall. Tilt is a unique experience too, and the wait time was manageable.
One thing to keep in mind: if you’re visiting during a busy time, like summer or a long weekend—expect long lines. We waited about an hour, especially for The Ledge, which was extremely crowded. At times, the Ledge space is shared with multiple groups, although you still get a turn for photos (whether you’re visiting on your own or with family).
In short, Skydeck is the more iconic, must-do experience, while 360 Chicago is a more relaxed and less crowded alternative.
Later, we stopped by North Avenue Beach. It was extremely crowded, but still beautiful and with a lot going on. Honestly, it was more crowded than any beach I’ve seen in the U.S., especially on such a sunny day. Once you move slightly away from the main crowd, the skyline views are absolutely worth it.
Final day: food, cafés, and one last stroll
We wrapped up the trip with breakfast at Wildberry Pancakes & Café. It’s very popular, especially on weekends, with long waits even around late morning, so we chose to go on a weekday when the wait was shorter. They don’t take reservations by phone or online, but overall, it was definitely worth it.
For food, we tried Giordano’s for their famous deep-dish pizza, explored a few Indian restaurants, and visited several cafés and dessert spots along the way. Everything we tried was good.
One standout was Molly’s Cupcakes. The desserts were delicious, and the playful swing seating made the experience even more fun and memorable.
A few things we skipped
We skipped the Adler, Aquarium and the Field Museum this time since we wanted this trip to focus more on the city itself, its neighborhoods, architecture, riverwalk, and lakefront.
Final thoughts
What stood out most about Chicago was the vibe. It felt lively, scenic, and energetic while still keeping its charm.
Between the riverwalk, skyline views, the architecture tour, observation decks, beach, cafés, and food, it was one of those trips that felt full without feeling overwhelming.
Even with the long weekend crowds, we had such a great time.
Chicago officially became one of my favorite downtown cities, and I’d definitely go back, especially to explore more in the summer. One thing to keep in mind is that Chicago weather can be unpredictable. It can be rainy, sunny, and windy all in the same trip, so it’s best to plan accordingly and avoid booking activities too far in advance without checking the forecast.
Chicago has two main airports. O’Hare was the one with a direct flight (like ours from Seattle), while the other, Midway, is smaller and may be closer to downtown depending on where you’re flying from and flight availability.
One thing we did notice was that the traffic from the airport to the downtown Loop area was really bad and barely moving at times. However, once we were within downtown, it didn’t feel as bad. For getting around, we either walked or took Ubers when the distance wasn’t easily walkable.
Public transportation is also a good option—Chicago’s trains and buses are well-connected and can help you avoid traffic, especially when traveling to and from the airport or getting around downtown.
If there’s one takeaway from this trip, it’s that timing and planning can make a big difference. Visiting popular spots during off-peak hours, choosing between experiences based on what you value most, and keeping plans flexible can really help you make the most of your time in the city.
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