The Ultimate Chicago Summer Bucket List

The Ultimate Chicago Summer Bucket List

Each year, usually sometime around spring break, my family sits down at the table to create our summer bucket list. This started when my firstborn was quite small and we realized that if we didn’t put it in writing, it would quickly be forgotten and then we’d be left with regrets, You see, we are a military family and our time in each city we live in is short. Our days are numbered if you will. So this year we sat down and made our list, only to find out a month or so later that this would in fact be our last summer in Chicago, making the list ever more important and meaningful. We NEEDED to accomplish the things on the list, to see the things we hadn’t yet seen. With that in mind, we pulled the kids out of school on a cold day in May (who would have thought that it would still be only 40 degrees in the middle of May!) and set out to check off some boxes on our Ultimate Chicago Summer 2019 bucket list. We spent the day as tourists and I’m telling you, it was the best day we’d had in a long time.

We hopped the train out of the suburbs of which we reside and headed into the city. My kids LOVE public transportation so even the 6:00 am train was exciting for them. Our first stop of the day was Willis Tower. If you’re a Chicagoland native, you’ll call this the Sears Tower. For all you non-locals, the landmark was renamed in 2009, after the Willis Group Holdings leased the naming rights. Regardless of what you call it, it’s a must see. The views are spectacular and unrivaled.

My husband is notorious for arriving early everywhere we go, so it was no surprise that we got to Willis Tower prior the Skydeck opening. This worked to our advantage as we found some delicious bagels in a pop up location on one of the lower levels. Pop up shops have become trendy recently, as they offer a variety of options in a spot where space can be limited. If you’re lucky enough to catch NYC Bagels at Willis or at any of their other locations, check them out, you won’t be disappointed. Delish!

Another great reason for getting to Willis early, you skip the lines! Our 9:00 reservation ensured that we were some of the very first guests of the day. The wait for the elevator, which I’m told can be hours, was less than three minutes. Once inside, we headed up at speeds of 18.2 miles per hour! Don’t worry, they slow the elevator down slightly on windy days. We reached the top quickly and had free roam of the immense 360 degree viewing room, allowing time to take in some stunning views of the city below us. My kids both agreed that the world outside looked like a tiny model you’d see in a train museum. We had fun finding all the places we’d been before, as well as searching out the places we planned on visiting that day. If you visit Skydeck’s website ( you can find activities for the kids, including fun facts, quizzes, coloring pages, and even a scavenger hunt.

The wait for the SkyDeck was also non-existent at 9:00 in the morning, so we were able to walk right into a box for our ninety seconds of awe. The Ledge has a pretty cool story of how it came to be, you can read it here

My son has a mild fear of heights and even he ventured out. He manned the camera and got some great photos of the occasion. I could have curled up with a good book and spent the entire day out there, lingering 103 stories up in the air, the city unfurling below me. It was incredibly relaxing. We spoke with the friendly elevator operators, who agreed that we picked the perfect time of day to visit, noting that they usually had a rush around lunch time and of course, on the weekends. If your schedule only allows you to visit during peak hours, consider purchasing the Fast Pass, which will get you out onto The Ledge much quicker! 

Once we had our fill of the view from the top, we headed down to water level and hopped aboard a Shoreline water taxi. The dock is conveniently located just steps from Willis Tower and the staff was amazingly friendly. As I mentioned earlier, it was a chilly morning, so we were the only ones aboard. Since we boarded at Willis Tower, we took the river route, which was a scenic, relaxing ride out to Navy Pier. Although I’ve walked along it, I’d never been on the Chicago River before and I was blown away at the views. There was so much to see, so many different, incredible buildings and the bridges- oh my goodness! My kids love all things mass transit, but being on a boat topped all other forms. They pretended to be pirates, sailors and fishermen, all while waving at everyone they saw from the deck. We saw quite a few other boats on the river, but never was there the stress of driving in downtown traffic. It was wonderful!

Ultimate Chicago Summer Bucket List on shore

At Navy Pier, we wanted to do the tourist things, so we planned on riding the Centennial Wheel. First we enjoyed the serene walk through the Crystal Gardens, an indoor, one acre botanical garden. There were fountains that hopped from one pool to another, palm trees and lush green foliage. For a moment we forgot that it was only forty degrees outside. That is, until we stepped through the sliding doors and were affronted by a cold gust of wind. We braved the cold and hopped on the wave swings, which would be tons of fun on a warm summer day. By the end of the ride, chilled tears of laughter were rolling down my cheeks. It was a nice reprieve to climb into the enclosed cabins of the Centennial Wheel and warm up. From the top of the wheel, we again had amazing views of the city and out over Lake Michigan. I was surprised at how comfortable the seats were, and how many different things you could see from different seats within the cabin. Since the cabins are enclosed, I had no qualms about having the kids along for the ride. It was safe, secure and lots of fun for all of us. 

From Navy Pier, we caught Shoreline’s water taxi again and took the lake route out to Shedd Aquarium. We’ve walked from Union Station all the way out to Museum Campus in the past. In the summer, with two kids. Let me tell you, after riding on the Shoreline water taxi, I will NEVER walk again! What a relaxing way to spend time, taking in the impressive view of the Chicago skyline, kicking our feet up and laughing as the boat made its way smoothly across the lake. 

The Shedd Aquarium is one of the things that repeats yearly on our bucket list. It never disappoints. We usually head into the city early and get in before it gets too busy, but since it was our third stop that day, we arrived in the afternoon, around 1:00. Knowing from experience that we’d want to see the aquatic presentation, known to kids everywhere as “the dolphin show”, we headed down to the Oceanarium to get tickets. The first available show wasn’t until 3:30, so a word to the wise, if you arrive during peak hours and you’re there with impatient kids, head straight to the Oceanarium to claim your spot, then resume your regular tour. The Polar Play Zone is also a great place to keep small hands busy while waiting. There is a small cafe with underwater windows that look into the depths of the dolphin tank. Here you can relax, grab a snack and enjoy the playful dolphins as they swim past. Once the time arrives for your turn at the show, try to sit near the front, to the left if you’re facing the audience. From here, you’ll have a front row view of the animals as they bring them out to the stage. My kids love getting a close up view of the sea lion as it lumbers out to greet the crowd.

There are many things to see at the Shedd, and so much to learn. My family enjoys strolling through each exhibit slowly and every time we visit, we see something new. A few of our favorites include spotting the sea turtle in the Caribbean Reef, the anaconda in Amazon Rising, and the giant isopod in the Waters of the World, but our favorite place to be is at the glass inside the Wild Reef exhibit. Even in a room full of people, it’s easy to relax among the coral, as fish of all kinds slowly swim past. If you sit long enough, you might be lucky enough to catch a glimpse of the sawfish, a truly remarkable creature! The docents working at the aquarium are knowledgeable, friendly and patient, especially with an inquisitive ten year old who has tons of questions!

The Shedd Aquarium makes a huge effort to ensure that everyone can enjoy a visit and has many accessibility accommodations. A sensory friendly app, geared towards autistic and sensory sensitive patrons can be helpful when planning your visit. For more information, click here

Ultimate Chicago Summer Bucket List  on water taxi

By the time we finished up at the Shedd, the clouds had cleared and the sun was warm in the sky. We hopped aboard the Shoreline water taxi for one more ride and it was the best ride of all. We took the “long” route, which combined the lake route and the river route. We encountered some of the same crew we had met earlier in the day, and were greeted with smiles and questions about our adventures. We felt like VIP’s! Because the weather had warmed, the boat was much more full on the return trip, which made it all the more fun. The crew handed out paper “First Mate” hats to kids and grownups alike and everyone enjoyed a laugh and a smile. Shoreline’s water taxis have become our new favorite mode of transportation. We never once had to worry about traffic or overcrowded CTA stations. The scenic views, friendly people and abundant laughter were the perfect way to travel as we checked off items on the Summer of 2019 Bucket List. Now we can’t wait to check out Shoreline’s Architecture tours!