Travel
There’s something magical about finding a hotel that doesn’t just accommodate your stay but enhances your entire travel experience. As a mom who’s stayed in countless hotels across the globe, I can confidently say that StayPineapple Chicago isn’t just another place to rest your head—it’s a destination in itself that’s capturing the hearts of Gen-Z travelers and cool people of all ages. Bonus: Did you know StayPineapple Chicago is the most Pet Friendly Hotel?
A Historic Building with Modern Vibes
Housed in a National Historic Landmark building in Chicago’s vibrant Loop district, StayPineapple seamlessly blends old-world charm with contemporary flair. The moment you step into the bustling lobby, you’re transported to what feels like the city’s coolest gathering (minus any awkward drunk uncles asking you weird questions). The old-school door keys add to the vintage appeal, though fair warning—losing one will cost you a $50 fee!
During my recent stay celebrating my daughter’s 20th birthday with tickets to Moulin Rouge at the nearby Cadillac Theatre, I was immediately struck by the Instagram-worthy elevator area and the building’s authentic Chicago character. As a native Chicagoan who’s experienced many hotels in my beloved city, the historic architecture combined with playful modern design creates an atmosphere that feels distinctively Chicago without any of the cookie-cutter hotel vibes.
Location, Location, Location
For travelers wanting to experience the best of Chicago, you simply can’t beat StayPineapple’s prime location. Situated in the heart of the Loop, you’re literally steps away from:
- The Theatre District (perfect for Broadway show enthusiasts)
- Millennium Park (hello, Bean selfies!)
- The Art Institute of Chicago
- The glamorous boutiques of the Magnificent Mile
- The architecturally stunning Rookery Building
- Lakeshore East Park (ideal for those traveling with pets)
From my room, I fell asleep gazing at the iconic Chicago Theatre marquee and the twinkling city lights. For shoppers, Primark is nearby, and coffee lovers will appreciate being within walking distance of the Chicago Starbucks Reserve. The central location means you can reach practically any major Chicago attraction within minutes.
The Naked Experience: Sleep Like You’ve Never Slept Before
Let’s talk about what StayPineapple calls “The Naked Experience”—quite possibly the most comfortable hotel beds on the planet. As someone who had unfortunately received both MMR and pneumonia vaccines right before our trip, I can personally attest that StayPineapple’s heavenly bedding saved our vacation.
Each room features:
- Ultra-plush, cloud-like mattresses that make your bed at home seem like a park bench
- Individual European-style duvets that eliminate the dreaded cover-stealing midnight tug-of-war
- Incredibly soft pineapple-embroidered robes that you’ll be tempted to smuggle home
- Minimalist room design with just the right touch of quirky pineapple accents
I’ve stayed in luxury hotels worldwide, but I’ve never experienced bedding that comes close to the comfort level at StayPineapple. I’m still trying to figure out how to recreate this sleep experience at home!
Officially the Most Pet-Friendly Hotel Brand in America
If you travel with furry family members, StayPineapple isn’t just pet-friendly—they’re downright pet-obsessed. They’ve been recognized with numerous awards including being listed as one of the Best Pet-Friendly Hotels in Newsweek’s 2025 Readers’ Choice Awards and ranked #1 in BringFido.com’s list of Top Dog-Friendly Hotel Chains.
Your four-legged companions receive:
- A special Staypineapple dog bed for use during your stay
- A Staypineapple treat tin (afternoon delight for dogs!)
- A collapsible water bowl to keep
- Walk-friendly waste bags in a yellow holder
Unlike many hotels that claim to welcome pets but make it difficult to actually enjoy your stay with them, StayPineapple truly accommodates your entire family—fur members included. They even let you leave your pet in the room while you explore the city (just use their special door hangers to let staff know).
The Little Touches That Make All the Difference
What sets StayPineapple apart are the thoughtful details that show they’ve genuinely considered what travelers need:
- Complimentary yellow umbrellas for unexpected Chicago downpours
- Bicycles available for exploring the city
- Afternoon treats and coffee in the lobby
- Friendly staff who seem genuinely happy to assist with any request
- Unique pineapple-shaped cookies that taste as good as they look
The team at StayPineapple has clearly put thought into creating not just comfortable accommodations but a memorable experience. Their “Everything People” approach means that every staff member is empowered to make your stay special.
Worth Every Single Penny
While StayPineapple isn’t the cheapest option in Chicago, the value you receive far exceeds the price tag. From the unparalleled comfort of their beds ( I cannot put a finer point on how damn comfy these beds are) to the prime location and exceptional service, you’re investing in an experience that elevates your entire Chicago trip.
As a mom who values both comfort and creating special memories for my family, I can honestly say I’ve found my new favorite Chicago hotel. There’s something refreshing about a boutique hotel brand that maintains its personality while delivering five-star comfort. Whether you’re a Gen-Z traveler looking for Instagram-worthy moments, a family celebrating a special occasion, or anyone who appreciates the perfect blend of luxury, comfort, and playfulness, StayPineapple Chicago delivers an experience that will have you planning your return visit before you’ve even checked out. Believe me, I’m just trying to decide on a city! South Boston StayPineapple, I’m coming for you! We’ve always stayed at the Hyatt Regency Boston and love it. It’s amazing but I’m not sure the beds can compete with StayPineapple.
And isn’t that what we’re all looking for? Not just a place to stay, but a place that makes us want to staypineapple.
If you want to see how awesome StayPineapple Chicago really is be sure to stop by my Instagram over the weekend. I promise you’ll be glad you did!
What’s your favorite go to hotel when traveling?