Earlier this year, I made my way to Chicago for the first time, and despite the freezing temps and wind that slapped me straight across the face, I was smitten. I mean, I’ve heard so many incredible things about Chicago, and once I visited, I got it! The food, the architecture, the energy, all the makings of a great city!
But, one thing almost every local said to me during that trip was, “You’ve got to come back in the summer!”
Fast forward a few months, and my wife was invited to deliver a keynote for United Airlines. Naturally, I tagged along, because any excuse to revisit a city I already love? Count me in! This time, we checked into Staypineapple Chicago, and from the moment we walked through the historic doors of this cheeky little hotel, I knew we were in for a good time.
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Before I go any further, let’s clear something up — Staypineapple is not a swingers hotel 🙃. I had so many people slide into my DMs asking this when I posted that I stayed there. The pineapple theme is cute and quirky, but not that kind of party.
That said, this brand does have personality, and I LOVE that! Staypineapple leans all the way into the fun with its bold yellow accents, playful messaging, and what they call the “Naked Experience.” And no, it’s not what it sounds like either. It’s just their version of peak cozy: fluffy robes, oversized towels, and soft European-style bedding with individual duvets so you’re not fighting your partner for covers at 2 a.m. Bless them.
They’re also super pet-friendly, and it’s no hidden fees, no weird rules; your pet is welcome just like you are.
Location
Staypineapple has locations in cities like New York, Boston, Portland, Seattle, San Francisco, and San Diego, but each hotel has its own unique vibe. The Chicago one has that old-school charm with a punch of personality.
Staypineapple Chicago is smack dab in Chicago’s Loop, which is perfect if you’re looking to be within walking distance of some of the city’s amazing attractions. Whether you’re into art, architecture, food, or just wandering aimlessly like I tend to do, this spot has you covered. It’s housed inside the historic Reliance Building, so if you’re into buildings with character and a backstory, Staypineapple Chicago checks those boxes.
What’s Nearby:
- Millennium Park (the “Bean”) – 5 min walk
- Art Institute of Chicago – 6 min walk
- Chicago Riverwalk – 10 min walk
- Lou Malnati’s (because deep dish is non-negotiable) – 8 min walk
- CTA Red Line – 2 min walk
Food & Drinks at Staypineapple Chicago
There’s something incredibly convenient about having a restaurant right in the hotel when you’re not quite in the mood to deal with crowds or make decisions. Atwood, the on-site restaurant serving up American comfort food, makes it very easy to just roll out of bed and straight into a cozy table by the window.
Staypineapple Chicago also offers a “complimentary” beer, wine, or fountain drink during happy hour, and cookies that will test every ounce of your self-control. You’ve been warned.
They also provide a reusable water bottle you can fill up at their filtered water station, which is a nice sustainability touch. Just FYI, things like this, along with the fitness center, Wi-Fi, streaming services (which weren’t working during our stay), and daily cookies, are covered under a daily ‘amenity fee’. Something to keep in mind when budgeting your stay.
The Rooms
We stayed in both a regular room and a suite, and it was cool to experience the difference. The standard room had everything we needed; clean, comfortable, and super cozy, with Staypineapple’s signature robes and duvets that I seriously considered stuffing into my suitcase. Also, I cannot stop talking about the bed!! It was one of the most comfortable beds I’ve ever slept in!
The suite is where we were able to stretch out a little more. It had a separate sitting area, perfect for lounging and watching TV. The layout gave us a bit of breathing room, especially after a full day of running around the city.
That said, while the historic charm of the building is undeniable and the city views were iconic, I do think some upgrades are needed, especially in the bathroom. The finishes felt dated, and a few modern touches would go a long way. The same goes for the furniture.
Whether you’re tagging along on your partner’s work trip (like me), visiting for the first time, or returning to fall in love with the city all over again, Staypineapple Chicago is a fun, quirky spot with a lot to offer. The location is unbeatable, the hospitality is warm, and the beds alone are worth booking a stay!
CHECK OUT PRICES FOR STAYPINEAPPLE CHICAGO
Need-to-Know Info
- Check-in: 4:00 p.m.
- Check-out: 12:00 p.m.
- Pet-friendly: Yep! No extra fee
- Resort fee: $24.95/day (includes water bottle, cookies, coffee/tea, and bike rentals)
- O’Hare International (ORD)
- By car or taxi: Approximately 22–23 minutes (no traffic)
- By CTA Blue Line subway: Around 44–45 minutes, nonstop from the Loop to O’Hare
- Midway International (MDW)
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- By car or taxi: Roughly 19 minutes (no traffic)
- By CTA Orange Line train: About 31 minutes direct from Midway to the Loop
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Planning a Trip?
- Find cheap flight and hotel packages with Expedia.
- Book your travel insurance with SafetyWing or World Nomads. You never know when you might need it. Lost luggage, trip cancellation, accidents. Better to be safe than sorry.
- Don’t forget these packing essentials
