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Chicago Uncovered Part 2: Explore the Windy City

By Charlotte Linde September 5, 2023

After breaking down why you absolutely should experience Chicago using Chicago CityPASS® in this article, I promised I'd share even more about my fun weekend trip. From the incredible Sheraton Grand Riverwalk stay to catching The Blue Man Group, I've spilled all the juicy details right here in this comprehensive article about my journey. If a Windy City escapade is on your horizon, this read is a must – packed with some valuable insights! And guess what? I'm already counting down to my next trip, this time with my teens in tow. 


The author was hosted by Chicago CityPASS®, Sheraton Grand Riverwalk and Blue Man Group to facilitate writing this article. All thoughts and opinions expressed are their own.


Ok, so let's get into what I ended up doing in Chicago with my Chicago CityPASS® and beyond.

Dive into the Depths at Shedd Aquarium:

The Shedd Aquarium offers a captivating immersion into the marvels of marine and aquatic life from across the globe. Among the highlights, the beluga whales and dolphins have always been my personal favorites. I think this stop on my trip is where I took the most pictures and videos, mesmerized by the coral reefs and beautiful fish.The aquarium truly provides a unique window into the intricate aquatic ecosystems. The Shedd Aquarium's exhibits not only awed me but also tapped into the vital importance of preserving these diverse marine habitats for generations to come. It's undeniably a perfect destination for families to explore and learn about the enchanting world beneath the waves.

Stargazing at the Adler Planetarium:Image by Leonid Andronov www.canva.com/design/DAFtm-C0o4E/BTCJdEceAL0s__H7gQy7mw/

Get ready to be blown away in a celestial haven where the universe's secrets take center stage. Imagine soaking up captivating sky shows (my top pick was "Planet 9") and diving into interactive displays. It's like embarking on an out-of-this-world cosmic adventure, exploring galaxies, planets, and stars.  Oh, and let me spill the beans about the café – the food there is incredibly delish! But that's not all – if you've got kids in tow, you're in for a treat. There's a kids' explore section that's like a mini-universe of fun and learning. Want a sneak peek? Check out [Reference URL]. Trust me, this place is the real deal when it comes to exploring the universe and having an absolute blast while you're at it!

360° Thrills at 360 Chicago:

So, picture this: I'm at 360 Chicago, heading up to the observation deck. And let me tell you, the city's epicness spreads out in all directions. The iconic skyline lit up at night - It's like a mega wow panorama. Now, here's the deal – there's this thing called TILT. You basically lean out from the building. I'll admit, I felt a bit dizzy and decided not to try it, but I heard it's an amazing experience. Instead, I soaked in the epic views and trust me, they were nothing short of spectacular. Curious for a peek? Check out [Reference URL]. It's all about taking in the awesome vibes of Chicago from up high!

Shoreline Sightseeing Architecture River Tour: (my favorite!)

This tour is like a front-row seat to Chicago's architectural wonders. As we cruised down the majestic Chicago River, I couldn't help but be in awe of the city's iconic skyline and stunning buildings. The knowledgeable guide's commentary added a whole new layer of appreciation, unveiling the stories and history behind each architectural masterpiece. What truly sets this experience apart is the unique vantage point. Seeing Chicago's landmarks from the water is a game-changer – you'll discover intricate details and perspectives you might have missed from the land.Shoreline Sightseeing Architecture River Tour: Cruise down the Chicago River and soak in the city's architectural wonders from a whole new angle.

Immersive Entertainment with Blue Man Group:

We caught the famous Blue Man Group show, and let me tell you, it's a belly-laughing good time! It's not on our Chicago CityPass radar, but we snagged the chance anyway. The show's a creative bombshell that mixes music, comedy, and interactive eye candy. Honestly, it's a show you absolutely can't afford to miss. Trust me, I was spellbound from start to finish – it's like they've got this magical grip on your senses and imagination. The Blue Man Group? Total artistic champs. They blew us away with their mind-blowing innovation and talent. Wanna check it out for yourself? Hit up [Reference URL]. Seriously, this is immersive entertainment at its finest!

A Must-Do: The Navy Pier Riverwalk:

I can't believe this place isn't talked about more. When I walked from my hotel to the pier, my jaw dropped. Being originally from the east coast, I've missed the ocean. While Lake Michigan isn't quite the same, this place satisfied that ocean longing in me and made me kick myself that I have never brought my kids here. The Navy Pier is like a whole world compacted into this spot. The beach, shopping, incredible views, attractions that'll blow your mind, and an atmosphere that's nothing short of electric. This isn't just your typical tourist spot – it's a full-on experience.

I was completely floored by the sheer amount to do. I mean, from iconic rides to upscale restaurants to Chicago Dogs - the Navy Pier is a goldmine of entertainment. Oh, and don't let me forget the view. You're right there on Lake Michigan, and the view is flat-out breathtaking. I could've easily spent hours just soaking it all in. Long story short? If you're in Chicago, Navy Pier is an absolute must-visit. Seriously, go check it out and save your thanks for later!

Retreat to the Sheraton Grand Riverwalk:

At the Sheraton Grand Riverwalk, I found a peaceful oasis amidst the city's vibrant buzz. Positioned right along the Chicago River, this hotel showcased breathtaking cityscape views.   Its prime riverfront location offers captivating city panoramas and convenient access to popular attractions. The hotel's strategic location made it possible for me to walk to many of the places I wanted to cross off my bucket list. The generously appointed rooms, coupled with modern amenities, foster an inviting ambiance for guests. With attentive staff and remarkable service, the Sheraton Grand Chicago stands as a remarkable option for both business and leisure travelers seeking an exceptional stay in the Windy City.

Tall Ship Windy: 

Although this stop was not a part of our hosted trip, 5 of us were given the opportunity to take sail aboard The tall Ship Windy. The Tall Ship Windy's Monday Night Blues Concert Series Sail is an unforgettable experience that combines the charm of sailing on a historic tall ship with the magic of live blues music. As the sun sets over Lake Michigan, passengers are treated to talented jazz musicians, creating a relaxing and atmospheric ambiance. The ship's crew is not only skilled in navigating the waters but also in offering a fun and welcoming experience. The combination of the gentle sway of the ship, the stunning views of Chicago's skyline (the absolute best way to see it!), and the enchanting jazz melodies makes for a truly unique and delightful evening. If you are looking for a memorable outing, the Monday Night  Sail on the Tall Ship Windy is a must-try experience that promises a memorable evening on the water. It was the perfect ending to my weekend trip. Check out my TikTok for a relaxing sneak peek:

Air and Water Show:

I got lucky with this one as it also was not planned in our hosted weekend. The Chicago Air and Water Show is nothing short of a spectacular display of precision and power in the heart of the Windy City. I consider myself incredibly fortunate to have stumbled upon this thrilling event while taking a leisurely stroll along Navy Pier. As jets roared overhead and watercraft showcases on Lake Michigan, I was treated to a jaw-dropping aerial performance that left me in awe. Like Top Gun stuff! The skill and daring of the pilots, along with the grandeur of the synchronized maneuvers, were truly a sight to behold. The Chicago Air and Water Show is an annual spectacle that not only highlights the city's rich military and aviation history but also offers an unforgettable experience for those fortunate enough to catch a glimpse. It's a testament to the city's liveliness and the magic that can be discovered in unexpected moments.

TIP: Getting Around- Use Public Transport 

Navigating Chicago was a breeze, thanks to the city's robust public transportation system. I found that a car was unnecessary, as the extensive bus and train networks took me anywhere I wanted to go at an incredibly affordable rate. For just $2.50 each trip or $5.00 for the full day - I could hop on a bus or train and explore the city without any hassle. This budget-friendly will allow you to focus on what the city has to offer without worrying about parking or traffic.

This adventure unlocked Chicago's best – diverse, captivating, and unforgettable. I will be back with my teens and most definitely purchase Chicago CityPASS® again - in Chicago and in another available city.