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    Skydeck Chicago - NEVER FORGET (look closely)

    Skydeck Chicago

    (939 reviews)

    The Loop

    Visiting Skydeck Chicago was easily one of the highlights on my weekend. I've seen plenty of city…read moreviews before, but nothing quite compares to standing that high up and seeing all of Chicago stretched out in every direction. There's a bit of a wait depending on when you go, but it moves steadily and there's enough to look at along the way that it doesn't feel like you're just standing around. The top, though, it's completely worth it. The best part, of course, is stepping onto The Ledge. Standing on a glass box looking straight down at the city is surreal, and definitely something you don't forget. It's one of those moments where you just have to pause and take it all in. If you're visiting Chicago, I'd say this is a must-do at least once. It's touristy, sure, but for good reason. The views, the experience, and that little rush of adrenaline make it totally worth it.

    Let me start by saying the main purpose of this visit was to step outside of my comfort…read morezone--because I am terrified of heights. The staff at Skydeck Chicago were all very sweet and friendly throughout the experience. As you make your way up, you walk through a series of exhibits and fun facts about Chicago, which was a nice touch and made the wait feel more engaging. It really highlights what makes the city special. Once we reached the top, I quickly realized I had underestimated just how high the building actually is. When it was time to step out onto the ledge... I completely punked out! They tell you not to look down, but of course, your natural reaction is to do exactly that. There's a photographer ready to capture the moment when you step all the way out onto the glass, but truthfully, I couldn't make it all the way out. I gave it about 2.5 seconds of bravery before my fear kicked in! Even with my moment of panic, I'm still really glad I went. It was definitely an unforgettable experience and a fun way to challenge myself.

    Chicago Riverwalk - PS. Chicago I love you.

    Chicago Riverwalk

    (258 reviews)

    The Loop

    One might expect me to be all doom and gloom about the sheer number of restaurants and bars along…read morethe river. Surprisingly, I won't be that guy, at least not this time. The main thing I really love about the Riverwalk is that it's a place in Chicago where someone can simply exist and vibe without the necessity of spending money. There is more than enough space to walk along the riverfront, take a seat, and enjoy the atmosphere. In terms of safety, there are more than enough "eyes on the street" as well as a visible police/private security presence. As with any high-traffic spot, use common sense, but other than a possible pickpocket, I don't foresee any issues. In terms of cleanliness, it is well-maintained, and I've not encountered any noticeable dirt, grime, or trash. I also really appreciate that the Riverwalk has both public bathrooms and is accessible! Accessibility needs no further explanation, and being able to wash up without buying an overpriced drink is worth its weight in gold. Another Yelper has compared it to the San Antonio River Walk and called out Chicago for having a shorter, less green "rip-off" of what one would find in Texas. However, I believe one should cast this comparison aside and judge the Chicago Riverwalk on its own merits. With that said... The final verdict: The Chicago Riverwalk is not your traditional, greenery-filled park. It is, however, a fantastic public space to take a stroll, have a bite, or just relax. Better still, while there is no shortage of tourists, it is an excellent destination for locals and visitors alike.

    Chicago Riverwalk is this great pathway that takes you, as the name implies, right along the river…read more Basically to get there, it branches just off of the lake shore, just by a little bit, then you walked down and around, and you are there. From Navy Pier you will find signs to guide you to the actual pathway. Simple as that. Along the Riverwalk you will find a bunch of restaurants, a couple of places to have drinks; i.e.: cocktails, and/or coffee oriented drinks like lattes and cappuccinos, plus, I'm sure, they also have soft drinks and things like that. Mostly, you will find great and unique views of the city. In terms of the actual functionality of the Riverwalk, it's a great place to get your steps in, as it travels along the river for quite a ways. Once you reach the end, there you can turn around and walk back the other way. Especially if you're in the area, and you want to get some exercise in, it's a great place to do just that. The Riverwalk is lined with stairwells. Plus, a number of embedded, cement seats. Thus, if you want to take a break and just sit back and enjoy the day, you can do that along the Riverwalk, as well. Overall, it's one of those main examples of Chicago life. Chicago Riverwalk is a great place to find a place to eat and/or a great place to take a walk.

    Willis Tower - Entrance

    Willis Tower

    (1.5k reviews)

    The Loop

    Spontaneous visit to Sears Tower on a Saturday afternoon! I haven't been here since I was a little…read morekid, and that was before they added The Ledge and before it was renamed to Willis Tower, so I've been wanting to come back to experience it again. Surprisingly on a Saturday around 1:30pm, it wasn't crowded at all and there was 0 wait times for anything. I loved the museum you walk through before getting to the elevator that takes you up. The part featuring Chicago foods and the mirrored deep dish pizza was especially cool. When we got up to the top, we enjoyed the amazing views and then headed over to The Ledge. There are two lines, but it did not take long at all because they only allow people 90 seconds to take photos and there are multiple ledges. There's also a bunch of restaurants located here, so you could truly just make a day out of it. They also have other exhibits sometimes, and I think this time around it was the Color Museum. Love that they also added a Van Leeuwen ice cream shop recently!

    They have military discounts! But you can't take advantage of the discount unless you purchase…read moretickets onsite. We were not prepared for the crowd on a weekday. Pro tip, you can line up for entry 15 minutes before your entry time. But at about 17 minutes before entry everyone rushes to the line, lol. The line moves fast, so no biggie. Once you enter, you go through security (another line) then they do photos (another line) then you walk through several very interesting exhibits, with multiple photo opportunities (more lines) but my hubby was focused on getting to the top, so we skipped the photo ops. Next you get in line for the elevator. After shooting up so fast your ears pop, you are treated to a wonderful view that pictures just don't capture. If you choose to go out on "The Ledge" its another line. They also take your picture. I can attest that you can accomplish the photo without ever looking down. Yes it's a lot of standing in line, but how often are you up where planes are flying by at eye level? And boy is the city breath taking from this vantage point.

    Buckingham Fountain - Married with children fountain

    Buckingham Fountain

    (413 reviews)

    South Loop, The Loop

    If you are vising Chicago, this is one of the not to be missed iconic landmarks. The Buckingham…read moreFountain is managed by the Chicago Park District is one of largest fountains in the world. It features impressive water displays and stunning architecture in the beautiful setting of Grant Park. The Buckingham Fountain was built at a cost of $750,00 and it was dedicated on August 12, 1927. Philanthropist Kate Buckingham donated the funds for the fountain as a tribute to her brother, Clarence who was an art collector of Japanese prints. Kate collected medieval sculpture, tapestries, and decorative arts. In addition to the Clarence Buckingham Memorial Fountain she also donated a statue honoring Alexander Hamilton in Lincoln Park and her family's art collection to the Art Institute of Chicago. Clarence Buckingham had been a governing member and a trustee of the Art Institute and Kate was influenced by his association with the institution. The Buckingham Fountain was designed by architect Edward H. Bennett in a classic Art Deco style out of pink marble. The sculptural elements were created by French artist Marcel Loyau. The fountain resembles a rococo style wedding cake and was inspired by the Bassin de Latone and modeled on the Latona Fountain at the Palace of Versailles in France. The fountain symbolizes the vastness of Lake Michigan, with four groups of bronze seahorses representing the four states bordering the lake: Wisconsin, Illinois, Indiana, and Michigan. The fountain is able to propel 14,000 gallons of water per minute. At night the fountain comes alive with lights and dancing water jets. The fountain is known for being featured in the opening of the television show, Married with Children. The Buckingham Fountain stands as a symbol of Kate Buckingham's philanthropic generosity and her love for her brother and the City of Chicago. Enjoy a picnic one one of the well maintained lawns and seating areas near the fountain where you are to create a lasting memory in the heart of Chicago. I will always treasure my visit.

    Buckingham Fountain is absolutely stunning and a must-see in Chicago. The size, but unfortunately…read moreit was closed and empty for cleaning. Nonetheless the skyline backdrop make it the perfect photo spot. Whether you visit during the day or catch it lit up at night, it's a beautiful and iconic experience.

    Original Sears Tower - landmarks - Updated May 2026

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