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Staypineapple An Iconic Hotel The Loop

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Staypineapple An Iconic Hotel The Loop, 1 W. Washington Street, Chicago, IL -(888) 420-1644
Area: Chicago Loop - Millennium Park
(Map)
4.45
HOTEL RATING: 
EXCELLENT
4.45 out of 5 (1132 Ratings)
3.5 miles United Center
v11 mins driving
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The Spotlight on 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.
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4
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1 room
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2 guests
Amenities View More
y
Free Internet
E
Fitness Center
w
Non Smoking
r
Pets Allowed
q
Accessible
x
Free Breakfast
j
Free Parking
u
Swimming Pool
A
Business Center
B
Airport Shuttle
Other Amenities
` Meeting/Banquet Facilities
` Safety Deposit Box
` Air Conditioning
` Bar
` 24-Hour Front Desk
` Express Check-In/Check-Out
` Elevator
` Hair dryer
` Wheelchair accessible
` On-site parking
` telephone
` kitchenware
` Free Wi-Fi
` Restaurant(s)
` Daily Housekeeping
` English
` Non-Smoking Rooms Available
` taxi service
` Smoke alarms
` Fire extinguishers
` Guests can opt-out of daily cleaning service
` First aid kit available
` Cashless payment available
` Linens, towels and laundry washed in accordance with local authority guidelines
` Hand sanitizer in guest accommodation and key areas
` Invoices
` Staff trained in safety protocol
` Contactless check-in/out
` Food delivery
` ATM or cash withdraw on site
` Daily disinfection
` Facilities for disabled guests available
` Fitness center
` Ironing amenities
` Laundry services
` Luggage storage & lockers
` Non-smoking property
` Separate shower/bathtub
` TV & Movies/Shows
` Air conditioning in public area
` Heating in public area
` Desk/workspace available
` Allergy-free rooms available
` Cleaning products available
` Pets allowed (charges may apply)
` Bicycle rental (charges may apply)
` Valet parking (charges may apply)

Staypineapple An Iconic Hotel The Loop Guest Reviews

Overall Average Score: 
Excellent (4.45 out of 5)

Write a review

5

Exceptional - 5.0 out of 5

Hannah, Cudahy, visiting Chicago Temple

Beautiful hotel. The room was impeccably clean and the staff was superb. This will definitely be my go-to place the next time I am in downtown Chicago.

5

Exceptional - 5.0 out of 5

Laurel Tue, 10 June 2025

Exceptional

Liked: I was there for a Blues Festival and to see friends. It was the perfect location, and the hotel bar was a nice space to relax with a group!

5

Exceptional - 5.0 out of 5

Keegan Tue, 10 June 2025

Exceptional

5

Exceptional - 5.0 out of 5

Russell Wed, 4 June 2025

Quiet, clean hotel with historic...

Liked: Wonderful location, close to park and other Loop attractions, right by a train stop and super easy to get to Midway. Nice property, friendly staff.
Disliked: A lot more expensive than last time we stayed. But so is everything else.

5

Exceptional - 5.0 out of 5

Andrew Fri, 30 May 2025

Exceptional

5

Exceptional - 5.0 out of 5

Ella-louise Thu, 29 May 2025

Exceptional

4

Very Good - 4.0 out of 5

Kayla Thu, 29 May 2025

Very good

Liked: Location was perfect to explore Chicago and very close to many L lines. The room was a great size and very comfortable. There were a lot of nice touches like the reusable water bottle in the room.

3.5

Good - 3.5 out of 5

Gabriele Tue, 27 May 2025

Good location

Liked: Great location, friendly staff, vintage vibe. Complimentary drinks. Nice view.
Disliked: Facility is rather old, mattress very soft and saggy, bathroom is very small and needs updating.

5

Exceptional - 5.0 out of 5

Jacklyn Sun, 25 May 2025

Exceptional

Liked: Conveniently located in the theater district and a short walk to fantastic restaurants and attractions. Staff was hospitable and very quick to help! Overall a lovely stay

4

Very Good - 4.0 out of 5

Robert Sat, 24 May 2025

Lovely hotel, nice staff, great...

Liked: Location was excellent. Hotel was beautifully renovated to honor the historic nature of the building. Large windows with great a view down State Street to the Marshal Field building and Chicago Theater.
Disliked: The price was way more than we have ever spent in fifty plus years of international travel. Our “deluxe” king room was very small as was the bathroom. I felt the $24.95 Daily Amenity Charge (for a coffee maker, 1 bottle of water and a welcome drink) that was sprung on us when we checked in was inexcusable when paying $600/night. That fee was never listed in the booking description. Our three night stay was almost $1800. which is crazy since there is no complimentary anything such as breakfast or a pool/health facility just a sugar cookie in the afternoon. We had to stay there due to other family members in town for a grandchild’s graduation. I would never stay there again due to the expense.

5

Exceptional - 5.0 out of 5

Tommi Fri, 23 May 2025

Great, historic hotel with fantastic...

Liked: I did not have high expectations, mostly due to rhe name. The name sounded really odd and gave a weird, budget hotel vibe. But I will definitely stay here again. The staff of the restaurant and reception were friendly. The room had high ceilings and spectacular views. The desk was for once by the window and not against the wall. Breakfast is great. And the renovation of the building has been done with great taste.
Disliked: It’s a small thing but the coffee at breakfast was cold to lukewarm. Small thing and could have said something about it.

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Staypineapple An Iconic Hotel The Loop 1 W. Washington Street, Chicago, IL