Staypineapple, An Iconic Hotel, The Loop, Chicago (IL) - Deals & Reviews

perfect spot for exploring chicago's parks and theaters

During my stay, I loved that we were just a few steps from the Chicago Theatre and only an easy 900-meter stroll to Millennium Park, which made exploring the city a breeze every day. plus, I really appreciated the comfort of the duvet-style bedding that allowed for a restful night's sleep after long walks around downtown.

exceptional service made our stay truly special with personalized touches like free water bottles!

Incredibly clean. Super friendly staff.

Had a great time with friends! The staff was super friendly, and the location made it easy to explore Millennium Park and visit a local restaurant. The bed was incredibly comfy, perfect after a long day of sightseeing. Pro tip, the restaurant closes early, so plan accordingly if you're looking for a late-night bite.

One downside was the parking cost, which was pretty steep at $75 for overnight.

staypineapple has the perfect location for shopping and dining near millenium park and the art institute. the deluxe king room was spacious and featured a super comfy bed with cloud-like duvets. the complimentary water bottles and the fun pineapple touches in the room made it feel special. the friendly staff truly stood out, especially with the welcome drink at the bar.

do recommend

The location is fantastic, right in the heart of downtown. The staff is super friendly, and the decor is cozy and vibrant. My Deluxe Queen Room was spacious and comfortable, with really nice toiletries and a great view. I loved the little touches like complimentary pineapple cupcakes at check-in!

No free breakfast option available.

I had a great time at this hotel! The king bed felt like sleeping on a cloud, and I loved the fun pineapple touches in the room. The only downside was I could hear some noise from the street below, but it wasn't too bad. Pro tip, don't miss the free drink at the bar when you arrive! 🍹

100% recommend for a weekend vacation

Comfortable bed, exceptional location, with easy access to multiple L train lines for exploring the city and a delightful breakfast that made our mornings even better.

Valet service was disappointing.

Stylish, Stylish, Stylish

The building's architecture is eye-catching, with stunning views that made my mornings feel magical. The seamless check-in experience set the perfect tone for my stay, and fellow travelers, their complimentary pineapple cookies were simply delightful! Plus, I loved that the hotel is so conveniently located near the train station, making it super easy to explore.

Totally recommend! 🥰🍍

Perfect for a Weekend Getaway!

Absolutely loved my stay in the spacious Deluxe Queen Room! The staff were really friendly and went above and beyond to make my experience special, like having pineapple cupcakes at check-in. The location was superb, making it easy to explore downtown Chicago. One minor downside was the lack of free breakfast options, but the complimentary bottled water and tea were great touches.

my stay was fantastic! the hotel truly exceeded my expectations with its vibrant atmosphere and cozy decor, making it the perfect peaceful break. the staff was incredibly friendly and the location couldn't be better for exploring the best of downtown chicago.

no free breakfast option available.

Staypineapple is right in the mix of downtown—seriously, you're a hop away from some killer eats, like Garrett Popcorn and The Walnut Room! The welcome drink at the bar was a sweet touch, and that bed? Cloud nine comfy! Can't forget the cute pineapple vibes they sprinkle around the hotel.

Things got a little wonky with the fitness center—it was super tiny and felt drab. Plus, breakfast was a letdown. Soggy burrito action with no one to chat with made the vibe a bit off, as the staff didn't seem too engaged.

Great location and clean rooms. check-in took forever and luggage storage was lacking.

We absolutely loved our stay at this charming hotel! The boys had the best time exploring Millennium Park, which was just a short walk away. The staff were fantastic, and they truly made our visit special with little touches like complimentary drinks and cozy robes.

In my kids' opinion, having a microwave in the room would have been super convenient for warming up snacks.

The exceptional location in the Loop and the vintage charm of the building stood out during this stay. The comfortable Deluxe Queen Room provided a cozy retreat, and staff made the experience enjoyable by being warm and helpful. However, the customer service was inconsistent, with one staff member displaying a lack of hospitality that was disappointing. While the stay exceeded expectations overall, the mixed service experiences left an impression.