Weekend in Chicago

Our weekend in Chicago was something different this time around. We have been to the Windy City many times over the years—usually for shopping marathons, wild nights, or just to soak up the lively energy of the place. But this trip? It was about slowing down, breathing in the city’s sights and sounds, and most importantly, just enjoying each other’s company in a more peaceful, romantic way. From the moment we stepped out of the car and felt that Chicago breeze, We knew this trip was going to be special. 

We arrived in Chicago on a perfect Friday afternoon. After parking the car, we decided to stretch our legs by heading straight to Millennium Park. Now, honestly, we’ve never walked through Millennium Park, and now to our surprise the Chicago Jazz Festival was in full swing. The festival had attracted a good-sized crowd, but the vibe was laid-back, and the music... oh, the music. It gave the day an extra layer of magic. As we strolled hand-in-hand, the smooth jazz playing in the background seemed to synchronize with our mood, creating this kind of spontaneous soundtrack to our day. 

We couldn’t resist stopping by The Bean (Cloud Gate) for a quick photo session, because honestly, what’s a visit to Chicago without capturing that iconic reflection? It’s one of those things we had to do.  We spent a lot of time simply standing there, gazing up at our distorted reflections, laughing at how the angles made us look like funhouse mirror versions of ourselves. 

We wandered through the park, listening to the jazz, occasionally stopping to watch street performers, and feeling the warmth of the late summer sun. There’s something so refreshing about being surrounded by the hustle and bustle but still finding these quiet moments to appreciate the little things, like a shared laugh or the feeling of your partner's hand in yours. 

After our leisurely walk, we meandered over to Grant Park, which feels like an extended arm of Millennium Park, seamlessly guiding us to the majestic Buckingham Fountain.  The fountain’s towering streams of water shot high into the sky, catching the sunlight and sparkling as they cascaded down. We paused to soak it in, and naturally, the camera came out. We love being goofy together, and this was no different.  

From there, we wandered through the surrounding gardens, which were bursting with color. The meticulously landscaped flower beds were a feast for the eyes, and we took our time strolling down the pathways, hand in hand, stopping to admire the vibrant blossoms and snap a few more candid photos. The towering trees provided pockets of shade, making it the perfect place to enjoy a quiet moment. Every corner of the park felt like its own little haven, and we were fully immersed in the beauty of it all. 

We wrapped up our day by stopping at Raising Cane’s for some chicken fingers. Nothing fancy, but after all that walking, it hit the spot. We headed back to the hotel afterward to call it a day. It had been the perfect start to what would turn out to be a fantastic weekend. 

Saturday morning, we woke up feeling recharged and ready for a full day of exploring. First stop? Wildberry Pancakes and Cafe for breakfast. If you’ve never been, do yourself a favor and check it out. The atmosphere, and the service complimented each other perfectly, and the food was delicious. We loaded up on carbs because we had a day full of walking ahead, and we needed the energy. Plus, their coffee is excellent, so we were sufficiently caffeinated for whatever adventures came next. 

After breakfast, we decided to walk to the Chicago Cultural Center. It’s about a mile from our hotel, which meant more picture-perfect moments along the way, plus the chance to just chat, be silly, and take in the city.  

The Chicago Cultural Center is a gorgeous building with stunning architecture—seriously, the domes and mosaic ceilings are breathtaking. It was once the city’s main library and now serves as a cultural hub with free exhibits, concerts, and art displays. The building itself is a masterpiece, especially the Tiffany dome, which is the largest Tiffany glass dome in the world. We spent a good amount of time marveling at it, taking in all the little details in the stained glass and the intricate designs.

 If you’re an art lover—or even if you just appreciate beautiful spaces—it’s a must-see. Visitors can expect rotating art exhibits, live performances, and plenty of history lessons tucked within its walls. We wandered through a few art exhibits, taking our time to admire the work and chat about what we liked (and didn’t like). It was such a peaceful way to spend the morning. 

Our next stop was the Museum of Illusions, and honestly, this place was an absolute blast. The museum is filled with interactive illusions that mess with your mind in the best possible way. We spent so much time laughing at how confused we were by some of the exhibits. It’s the kind of place where you can let your guard down, and just have fun.

There’s everything from optical illusions that make you question reality to rooms that mess with your sense of space and balance.  We took turns playing tricks on each other, taking funny pictures where one of us looked twice the size of the other. The entire experience was full of laughs and just added to the light-hearted tone of our weekend. If you’re in Chicago and want to do something a little quirky, this is the place. 

After our museum fun, we made our way to the Northman Beer and Cider Garden down by the river. This was the perfect spot to take a load off for a bit, sip on some cold cider, and people-watch.

There’s something calming about sitting by the river, watching boats and kayaks glide by, and just soaking up the city's energy without being in a rush. It felt like time slowed down for us as we sat there, chatting and laughing, reflecting on how perfect the day had been so far. 

A Romantic Dinner on the Water 

After our Cider break, we headed back to the hotel to freshen up because we had a special evening planned: a dinner cruise on the Odyssey. We took a Lyft down to Navy Pier, which was bustling with people, but the mood was more romantic than chaotic as the sun started to dip lower in the sky. 

The dinner cruise was the highlight of the trip. As we boarded the Odyssey, the boat's sleek, elegant design set the tone for what would be a memorable evening. The staff greeted us warmly, and we were led to our table, which had the most incredible view of the Chicago skyline. There’s something magical about seeing the city from the water, especially at sunset.  

Dinner was phenomenal—delicious courses served at a leisurely pace so we could really enjoy each other's company and the beautiful setting. The food was excellent, but the real magic was in the atmosphere. There was soft music playing in the background, and the boat cruised gently along the lake, giving us a front-row seat to one of the best views in the world. We clinked our glasses and toasted to us, to love, and to another wonderful Chicago adventure.

As the evening went on, we wandered out onto the deck to take in the views. The wind off the lake was cool, but not cold, and we stood there, side by side, watching the skyline shimmer from the setting sun. It was one of those moments that makes you stop and realize just how lucky you are to be sharing it with someone you love. 

By the time the cruise docked and we headed back to the hotel, we were completely content. Chicago had once again given us a weekend to remember—one filled with laughter, love, and just the right amount of adventure. 

What A Trip!