My first visit to Chicago was back in 2000, exactly 15 years ago! My dad went for a business trip and he decided to extend it and make a family vacation out of it. So the first couple days when he was at work, my mom took my brother and I around downtown to explore and shop. I remember feeling very small and insignificant as I looked up at the massive skyscrapers that encompassed the city.

Now that I’ve grown up physically and mentally, not much has changed in terms of feeling tiny next to these towering structures. The concentration of skyscrapers downtown form a gorgeous skyline that can be seen from various viewpoints throughout the city. Based on the short amount of time we were there (around 36 hours) and the fact that everything needed to be within walking distance from our hotel, my opinion of the top three places to enjoy the Chicago skyline would be a stroll along the Chicago River, along Navy Pier, and from one of the buildings themselves, the John Hancock Center.

I'll share some photos that my dad captured back in 2000 juxtaposed with my 2015 pictures. I actually stumbled upon these old photos after I came back from Chicago so it was a pure coincidence that they happened to match my picture series.

Chicago River

The downtown area was bustling with people and we were easily distracted with all the livelihood and activity from nearby restaurants and shopping venues. The city was full of life on this sunny Saturday afternoon. I honestly felt like walking along the Chicago River was kind of like walking around the strip in Vegas. All the buildings looked so grand and the structures looked perfectly manicured. It almost felt artificial, like walking around The Venetian Hotel with the canal in the center, the painted bright blue sky above, and the fake windows above the shops.

Walking along the Chicago River, you can absolutely experience the towering feeling and admire the buildings up close and personal. I could barely capture a photo encompassing the full height of the buildings when I was along the river. It definitely brought me back to feeling like a little girl in a big city.

View from the Chicago river (2015) (notice the same building?)

View from the Chicago river, a little further down the road (2000)

Navy Pier

Navy Pier reminded me of Fisherman’s Wharf in San Francisco. There were plenty of seafood restaurants, families enjoying themselves in the amusement park area, and tourists taking in all the wonder. We walked along Navy Pier towards the Chicago Shakespeare Center and admired the skyline from the deck. It’s a great viewing point of the city from the waterfront. The amusement park also has a very tall ferris wheel, which is a great opportunity to get higher up to see the skyline.

We didn’t have enough time during this trip, but I would have wanted to board a boat and sail out onto Lake Michigan to get a view of the skyline from the water.

John Hancock Center

The Signature Lounge on the 96th floor of the John Hancock Center is a great viewpoint overlooking the city. You’re already in one of the highest buildings in the city so you have an amazing view of the other skyscrapers. There’s no entrance fee to go up to the 96th floor, although you will spend money buying drinks at the lounge. Drinks are on the pricier side, but it does come with the view. With that being said, I would rather come here than the Willis Tower (formerly known as Sears Tower) since you do have to pay an entrance fee over there. At the Signature Lounge, you will probably end up paying a similar amount but you get an added benefit of sitting comfortably at your table and enjoying a drink.

You also have a choice to wait a bit longer if you want to secure a lovely window seat. We went on a Sunday afternoon with five people and waited about 20-25 minutes for a window seat, so it wasn’t bad at all. We only ordered drinks as we had just eaten lunch prior to visiting the lounge, but we did sit and socialize for up to an hour and a half. At no point did we feel any pressure from the staff to leave our prime real estate of a table to make room for other waiting patrons. And again to add to my wishes for more time, if we had more time I would have loved to have brunch at The Signature Room on the 95th floor. Until next time!