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  • Writer's pictureAmanda Akers

Chicago: A Long Weekend Away

Updated: May 28, 2023

Oh Chicago, a perfect short flight for a weekend getaway!


Logistics:

  • Travel: We flew frontier from Charlotte to Chicago. I am usually an American Airlines flyer and now, I will stay that way after the experiences we had getting to Chicago.

    • We opted to take a late flight Thursday night so I wouldn't have to take an unneeded day or PTO and we scheduled our flight home Sunday later to arrive in time to get rest for work on Monday morning.

  • Lodging: We stayed that W Chicago - opted for a downtown hotel over an AirBnb due to cost and location

  • Getting around: we opted for walking (lots of walking), Ubers and the subway to get around.


 

My Top Recommendations

Brunch

Wildberry Cafe - while they don't serve alcohol, the food makes up for it! You definitely won't leave hungry

Activity #1

Bar

Activity #1


 


We rolled out of bed on Friday morning, feeling delightfully lazy, and made our way to the highly recommended Wildberry Cafe for breakfast. Let me tell you, that place lived up to the hype! The food was on point, and the atmosphere was so much fun.


With satisfied bellies, we sauntered through Millennium Park, excited to see Cloud Gate, aka "The Bean." I mean, come on, who can resist the allure of a giant, shiny bean? It was like stepping into a funky, reflective wonderland. We couldn't resist striking some goofy poses and capturing the perfect selfie.


After getting our art fix, we headed towards the waterfront and snagged tickets for a river architecture tour. It was like a crash course in Chicago's history, from the devastating Great Chicago Fire to the incredible rebirth that followed. The tour guide was a fountain of knowledge, and we soaked up every fascinating tidbit about the city's iconic buildings.


Once back on solid ground, we decided to hit up Magnificent Mile for some retail therapy. We happily wandered in and out of stores, indulging our shopaholic tendencies. Our ultimate destination? Stadium Goods.


As the sun began to set, we found ourselves craving an adrenaline rush, so we made our way to Chicago 360. Picture this: you're leaning out from the 94th floor of a skyscraper, the ground seemingly vanishing beneath your feet. It was equal parts thrilling and terrifying, but the views were absolutely epic. With our hearts still racing, we retreated to the CloudBar for some well-deserved libations. Sipping on our drinks, we marveled at the stunning cityscape below. The night was young, and Chicago had cast its spell on us. It was just the beginning of our urban adventure, and we couldn't wait to see what else this captivating city had in store for us.



The next day, we sprang out of bed and made our way to the Color Factory. Let me tell you, it was a wild and vibrant experience! Every corner was bursting with colors and interactive installations that brought out our inner child. We couldn't resist snapping selfies and getting lost in a rainbow of hues.


As we stepped outside, we were greeted by a bizarre sight - snowflakes falling from the sky in April! Talk about a surprise twist in our Chicago adventure. We embraced the magical moment, laughing and taking pictures.


We ventured to Stax Cafe for a hearty brunch. Once we were properly fueled, we hopped in an Uber and headed to the iconic United Center to pay homage to the one and only Michael Jordan.


After soaking up MJ's greatness, we decided to keep the good times rolling by venturing to Lincoln Park. And guess what? The zoo was free! We strolled through the animal-filled oasis, taking in the sights and sounds of nature. It was a perfect little escape from the bustling city.


By this point, our appetites were calling, and we knew there was only one thing we had to try in Chicago - deep dish pizza! We eagerly made our way to Giordano's, where we indulged in slice after slice of cheesy goodness.


With satisfied stomachs, we were ready for a truly unique experience at Whim. This immersive bar took us on a journey through time, making us ponder the past, present, and future. It was like stepping into a time-traveling adventure that had us questioning our very existence. Talk about a mind-bending night out!


As the evening wound down, we found a cozy bar near our hotel to catch a thrilling fight on TV while sipping on some late-night libations. The energy in the air was electric, and we cheered on our favorite fighters as if we were part of the action.


Exhausted but fulfilled, we finally called it a day, knowing that Chicago had delivered yet another unforgettable experience. From colorful adventures to snowy surprises, delicious deep dish to thought-provoking bars, this city had captured our hearts and left us yearning for more.



On our last day in Chicago, we couldn't miss the chance to attend a Chicago Cubs game at the legendary Wrigley Field. The atmosphere was electric, with cheering fans and the excitement of America's favorite pastime filling the air. We soaked in the sights and sounds, cheering on the team and joining in on the seventh-inning stretch. It was an unforgettable Chicago experience that left us with lasting memories of the city's passion for baseball.

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