Staypineapple An Iconic Hotel The Loop

After a long day of unexpected travel 'adventure' the awning of the Pineapple was a welcome sight. As we entered the building we were immediately taken aback by the beauty of the art deco style interior. The front desk staff at the Stay Pineapple are phenomenal! Their kindness, efficiency and attentiveness were impeccable. As we approached the front desk we were greeted warmly and with a smile. Check-in was easy and uneventful. (that's a good thing) A ride in the glamorous silver and black classic old Hollywood movie style elevator was a lovely way to be transported to our room. As the doors opened to our floor we were once again delighted by the beautifully ornate design and decor. Once in our room the functional and comfortable room layout made for a welcome respite from the busy city below. Even though this is touted as a pet friendly hotel there were no sights or smells of previous furry inhabitants. Our room was impeccably clean and serenely quiet. I truly can not express enough how lovely our stay was. Kudos to the staff from front desk to housekeeping for working together to make sure every guests needs and wants are met. We will definitely be back.

We spent two nights at the Staypineapple during our visit to downtown Chicago. It’s a great location with tons of restaurants, shopping and public transportation close by. The service was wonderful and the beds were relatively comfortable. We had a car and utilized the Valet which is a bit pricey ($75/day) and there is only one valet on staff at a time so plan on a little extra time to drop and retrieve your vehicle. The nightly cookies and complementary water bottle are nice touches. We will definitely be back for our next stay in the loop.

I love this hotel! The overall experience is probably one of the best I’ve had in my decades of traveling. I stayed here on my visit to Chicago for Pride month and this hotel has so much character and little details that makes you feel special as a guest. Its vintage building mixed in with the cute pineapple style is such a vibe! All the staffs ate very helpful and friendly as well. They offer to help with everything without you even asking. I provided captions for the photos of my favorite things in this hotel. But I forgot to add that they have cute vintage bikes you can borrow to use around the city! This hotel is just amazing. I also wanna give a shout out to their bar tender Maya who’s so great at her job and is very hardworking. I hope the management rewards their staff. They all seem happy to be working here. I’ll def recommend this hotel to all my friends visiting Chicago and I’d def come back!