Staypineapple An Iconic Hotel The Loop

Luxury Vibes in the Heart of Chicago's Music Scene

Modern comfort meets historic grandeur at Staypineapple An Iconic Hotel The Loop. Housed in a Daniel Burnham-designed building, this boutique hotel features gorgeous mosaic floors, marble ceilings, and elegant mahogany furnishings. Located in Chicago’s vibrant Loop, it’s just a short walk from iconic cultural landmarks and major music venues, making it a stylish home base for concert-goers.

Every room balances classic style with sleek, modern touches—think plush bedding, flat-screen TVs, and select suites offering Millennium Park or Lake Michigan views. With a fitness center, bike rentals, and pet-friendly perks, you’ll be well-equipped for both adventure and relaxation.

Check-in starts at 4:00 PM and check-out is at a generous 12:00 PM, giving you plenty of time to sleep in after a late night out.

Why Concert-goers love it

With top venues like the Chicago Theater and Millennium Park less than a 5-minute walk away, this hotel is ideal for those catching a show. You can walk to most events, skip the rideshare surge pricing, and be back in your room in minutes. Despite its central location, guests report a quiet, restful atmosphere—perfect for winding down. The later check-out time is a bonus for anyone who rocked out a little too hard.

Who this Hotel is great for

• Groups of friends looking to stay stylishly close to the action
• Solo travelers ticking a legendary artist off their list
• Couples planning a romantic concert weekend
• Fans wanting a quiet and luxurious place to recharge
• Budget-conscious music lovers who still want upscale touches

Food and Drink Options

While the hotel doesn’t have a full-service restaurant, it’s surrounded by walkable dining options that stay open late. You'll find everything from deep-dish pizza to upscale bites just steps away. Many guests appreciate the in-room coffee and snacks for a quick morning fix after a long night. Though there’s no on-site bar, the neighborhood is packed with options.

Nightlife Options

The Loop comes alive at night with nearby bars, lounges, and live music venues. From jazzy speakeasies to craft cocktail bars, there’s something for every vibe. The hotel’s central location makes it easy to hop from show to afterparty and still be in bed before sunrise.

What People Say

Guests love the charming historic details, the cleanliness, and the super-friendly staff. Many highlight how perfectly located the hotel is for exploring the city and attending concerts. The plush bedding and quiet rooms get frequent shoutouts as a major plus after a night out.

Areas for Improvement

Some guests mention that the hotel lacks an on-site restaurant or bar, which could be a downside if you’re hoping for room service or a nightcap without leaving the building. And while most rooms are spacious, a few guests found certain room layouts a bit snug.

The Bottom Line

For concert-goers who want historic elegance, modern comfort, and unbeatable location, Staypineapple An Iconic Hotel The Loop hits all the right notes.