Embarking on a journey to the Windy City in August 2023, we found ourselves amidst the vibrant streets and iconic landmarks of Chicago. Our two-part hotel adventure, coupled with immersive city explorations, presented us with a whirlwind of experiences, from awe-inspiring attractions to hotel stays that both delighted and challenged us. Join us as we recount our Chicago escapade, complete with valuable recommendations for fellow travelers.

Embassy Suites Magnificent Mile: Aug 13-15 Our Chicago adventure commenced at the Embassy Suites Magnificent Mile, a promising beacon nestled in the heart of the city. Greeted with efficiency and a thoughtful gift bag that acknowledged our Hilton Honors status, the check-in process was seamless. However, the hotel’s floor and elevator configuration proved puzzling, slightly tainting the initial impression.

Stepping into our suite, we were met with a familiar layout that blended comfort and functionality. The allure of a separate living area and cozy bedroom echoed the essence of a classic suite. Our mornings were graced with the allure of a typical hotel breakfast, complete with a range of offerings to satisfy diverse palates. Meanwhile, evenings beckoned with a delightful happy hour, further enhancing the sense of hospitality.

Nonetheless, the hotel’s dated appearance was impossible to ignore. Urgently in need of updates, aspects like the carpet’s condition and broken tiles in the bathroom were clear signs of wear. Despite these shortcomings, the attentive and supportive hotel staff remained a highlight, compensating for the less-than-ideal room conditions.

Sheraton Grand Downtown Chicago: Aug 15-17 Transitioning to the Sheraton Grand Downtown Chicago promised an elevated experience, characterized by an executive 1-bedroom suite thanks to our strategic use of Marriott Bonvoy cards and Platinum Elite Status. Anticipation filled the air as we left one hotel haven for another, eager to dive into all that the Sheraton had to offer.

However, a few hurdles awaited us. The process of checking in at the Sheraton proved to be less smooth than expected, lacking the acknowledgment of our status and essential details about the Sheraton Club and breakfast arrangements. The absence of baby changing stations compounded the inconvenience, leading to an impromptu car seat diaper change in a lobby restroom.

Once settled in, the suite’s lightly updated ambiance exuded comfort, with the living area’s well-furnished arrangements and the bedroom’s spacious design. The bathroom, although still in need of attention, maintained the Sheraton’s signature amenities that we grew to appreciate.

CityPASS Adventures and Recommendations: As part of our Chicago exploration, the CityPASS revealed its worth through a collection of attractions. However, navigating the pass’s intricacies demanded careful attention, with two options available for different numbers of attractions. Our three-pass selection allowed us to immerse ourselves in the wonders of the aquarium and the captivating architectural boat tour.

Tips for a Seamless Chicago Adventure:

  1. Hotel Choice: Prioritize your preferences when selecting accommodations, considering aspects like convenience, amenities, and brand loyalty.
  2. CityPASS Selection: Analyze the available attractions before choosing your CityPASS option, ensuring you make the most of your chosen attractions.
  3. Exploring Attractions: Plan your days thoughtfully to maximize your exploration time. Consider booking popular attractions like boat tours for late afternoon or early evening slots for an added scenic dimension.

Conclusion: Our journey through Chicago in August 2023 was a tapestry of highs and lows, of hotel discoveries and urban explorations. From the Embassy Suites’ warm hospitality to the Sheraton Grand’s pursuit of luxury, each hotel left its unique mark on our journey. Through captivating attractions like the architectural boat tour and the wonders of the CityPASS, we delved into Chicago’s essence, discovering a city teeming with history, culture, and architectural brilliance. As the sun dipped below the skyline, painting the city in hues of gold, we realized that our experiences, both the delightful and the challenging, were woven into the vibrant fabric of Chicago—a city that never ceases to captivate and inspire.