The Penthouse at Grand Plaza

Coming back in August 2025 felt almost like returning home, since we’d stayed at the Grand Plaza in 2019. Apartment 7 was comfortable, and the kitchen had everything we needed for vacation, even Zip Lock bags for city tours. There were extra towels for the lovely pool area, which has multiple grills. We had dinner there and chatted with the mostly resident tenants, who were extremely friendly. Lou and James helped with some special requests, and from the balcony we could see the Navy Pier fireworks. The Navy Pier trolley that used to stop at the front door is no longer there, unfortunately. But the bus line and Grand station are right by the building, so public transit gets you around the city. If we can save up for another trip, we’d stay there again.

I paid $4,000 for three nights at James’s property, but the experience was disappointing. Instead of a welcoming stay, it felt like a business-to-business transaction, with endless instructions and several PDF files full of rules. James’s attitude and management style don’t seem suited to hospitality, and I think substantial changes are needed for future guests to have a positive experience.

The view was spectacular, and the location made almost everything I wanted to do an easy walk. The Redline stop on the corner made getting to Wrigley Field for the Winter Classic simple. The grocery store is attached to the building, which made picking up anything I needed easy. At the Penthouse at Grand Plaza, the apartment was clean to my high standards and stocked with what I needed, even grocery bags so I didn’t have to buy any. The bed was comfortable, and the staff were exceptional. Thanks to Jim and Jeri-Lou for being so kind and hospitable. I couldn’t have been happier with my stay.

James, Jim, and Jeri-Lou were informative and helpful to deal with. They’re direct about keeping the condos immaculate and respecting the building and its occupants, and I respect how hard they work at it. This is a high-end condo with high standards, not a hotel, and that’s what appealed to me. If you want to throw big parties and trash the place, go somewhere else. The condo is spacious, fully equipped, and the deck is unbelievable. The amenities are among the best in Chicago, and there’s nothing I felt I was missing. Getting up around 4:45 or 5 a.m. to catch the sunrise is unmatched. The location is great too. I worried because of the reviews, but people should ignore them. It’s an amazing space, and I already can’t wait to stay here again on my next Chicago trip. Thanks to Jeri-Lou and the team for all your help.