Staypineapple, An Iconic Hotel, The Loop

4.0 star property
Hotel with a fitness centre, a quick walk to Cloud Gate
your current months are January, 2025 and February, 2025.
January 2025
February 2025

Photo gallery for Staypineapple, An Iconic Hotel, The Loop

Interior detail
Exterior detail
Front of property
Bar (on property)
View from property

Reviews

9.2 out of 10
Wonderful

Popular amenities

  • Laundry
  • Pet-friendly
  • Parking available
  • 24/7 front desk
  • Air conditioning
The price is AU$273
includes taxes & fees
26 Jan - 27 Jan

Get more when you're a member

  • Save 15% or more on select VIP Access properties when you reach Silver tier or higher
  • Experience top-rated quality and exceptional service
  • Get an in-stay perk at select properties, plus free room upgrades, early check-in, and late check-out when available

Room options

Available filters for rooms
Showing 10 of 10 rooms

Deluxe Room, 2 Queen Beds

Highlights

Air conditioning
Connecting rooms available
Free cots/infant beds
LCD TV
Hypo-allergenic bedding
Hairdryer
Designer toiletries
Bathrobes
  • Sleeps 4
  • 2 Queen Beds

Executive Suite, 1 King Bed

Highlights

Air conditioning
Connecting rooms available
Free cots/infant beds
LCD TV
Hypo-allergenic bedding
Hairdryer
Designer toiletries
Bathrobes
  • Sleeps 4
  • 1 King Bed

Executive Suite, Multiple Beds, Accessible

Highlights

Air conditioning
Connecting rooms available
Free cots/infant beds
LCD TV
Hypo-allergenic bedding
Hairdryer
Designer toiletries
Bathrobes
  • Sleeps 4
  • 1 Double Sofa Bed and 1 King Bed

Suite, 1 King Bed, Park View (Millennium)

Highlights

Air conditioning
Connecting rooms available
Free cots/infant beds
LCD TV
Hypo-allergenic bedding
Hairdryer
Designer toiletries
Bathrobes
  • Sleeps 4
  • 1 King Bed

Deluxe Room, 1 Queen Bed, Accessible

Highlights

Air conditioning
Connecting rooms available
Free cots/infant beds
Mini-fridge
LCD TV
Hypo-allergenic bedding
Hairdryer
Designer toiletries
  • Sleeps 3
  • 1 Queen Bed

Deluxe Room, 1 Queen Bed, Accessible

Highlights

Air conditioning
Connecting rooms available
Free cots/infant beds
Mini-fridge
LCD TV
Hypo-allergenic bedding
Hairdryer
Designer toiletries
  • Sleeps 3
  • 1 Queen Bed

Deluxe Room, 2 Double Beds, Accessible (Mobility Accessible with Tub)

Highlights

Air conditioning
Connecting rooms available
Free cots/infant beds
LCD TV
Hypo-allergenic bedding
Hairdryer
Designer toiletries
Bathrobes
  • Sleeps 4
  • 2 Double Beds

Deluxe Room, 2 Double Beds, Accessible (Roll-In Shower)

Highlights

Air conditioning
Connecting rooms available
Free cots/infant beds
LCD TV
Hypo-allergenic bedding
Hairdryer
Designer toiletries
Bathrobes
  • Sleeps 4
  • 2 Double Beds

Deluxe Room, 1 King Bed

Highlights

Air conditioning
Connecting rooms available
Free cots/infant beds
LCD TV
Hypo-allergenic bedding
Hairdryer
Designer toiletries
Bathrobes
  • Sleeps 3
  • 1 King Bed

Deluxe Room, 1 Queen Bed

Highlights

Air conditioning
Connecting rooms available
Free cots/infant beds
Mini-fridge
LCD TV
Hypo-allergenic bedding
Hairdryer
Designer toiletries
  • Sleeps 3
  • 1 Queen Bed
Mod logo
Sign in to view eligible discounts and perks. More rewards for more adventures!

Frequently asked questions

Is Staypineapple, An Iconic Hotel, The Loop pet-friendly?

Yes, dogs are allowed at this property. There's a fee of USD 29.95 per accommodation, per night. Service animals are exempt from fees.

How much does it cost to stay at Staypineapple, An Iconic Hotel, The Loop?

As of 21 Jan 2025, prices found for a 1-night stay for 2 adults at Staypineapple, An Iconic Hotel, The Loop on 26 Jan 2025 start from AU$225.60, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking at Staypineapple, An Iconic Hotel, The Loop?

Valet parking is available for USD 75 per night.

What time is check-in at Staypineapple, An Iconic Hotel, The Loop?

Check-in start time: 4:00 PM; check-in end time: midnight. After-hours check-in is not available.

What time is check-out at Staypineapple, An Iconic Hotel, The Loop?

Checkout is at noon.

Where is Staypineapple, An Iconic Hotel, The Loop located?

Located in Downtown Chicago, this boutique hotel is within a 10-minute walk of Chicago Cultural Center, Chicago City Hall and Cloud Gate. Chicago Riverwalk and Art Institute of Chicago are also within 10 minutes. Washington Station is only a 2-minute walk and Lake Station is 2 minutes.

Reviews

9.2

Wonderful

Rating 10 - Excellent. 724 out of 1002 reviews" "
Rating 8 - Good. 185 out of 1002 reviews" "
Rating 6 - Okay. 58 out of 1002 reviews" "
Rating 4 - Poor. 24 out of 1002 reviews" "
Rating 2 - Terrible. 11 out of 1002 reviews" "

9.4/10

Cleanliness

9.4/10

Staff & service

8.8/10

Amenities

9.2/10

Property conditions & facilities

9.2/10

Eco-friendliness

Reviews

10/10 Excellent

Juan

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 2 nights in Dec 2024

10/10 Excellent

Macey

Travelled with pets, Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
easy and nice valet and very unique style of the hotel
Stayed 1 night in Dec 2024

10/10 Excellent

Patricia

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Wonderful comfortable hotel near shopping theaters and the river. And Christkindel market Amazing location
Stayed 1 night in Jan 2025

10/10 Excellent

Melanie

Travelled with partner
Liked: Staff & service, amenities, property conditions & facilities
This property made you feel at home as soon as you walked in the door. I always enjoy the old-fashioned keys, rather than having a key fob to swipe. The whole building was perfectly clean and beautifully decorated.
Stayed 1 night in Dec 2024

8/10 Good

Sara

Stayed 2 nights in Dec 2024

10/10 Excellent

Jacob

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
It was a great stay with a great location
Stayed 4 nights in Dec 2024

8/10 Good

Michael

Travelled with family
Liked: Cleanliness, staff & service, property conditions & facilities
Really great hotel, our only issue was they did not have our selected room (2 queens). They upped us to a suite with a fold out bed, so we all did not get to experience the amazing beds.
Stayed 1 night in Dec 2024

10/10 Excellent

Riomar

Stayed 3 nights in Dec 2024

10/10 Excellent

Pamela

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The Atwood restaurant has great food, very helpful and pleasant staff but thay need more servers.
Stayed 1 night in Dec 2024

10/10 Excellent

Nancy, Jupiter

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The location of this hotel is fabulous. It is one block from the Blue Line train from O'Hare and convenient to all other train lines in the Loop. Theatres and Millennium Park are a short walk. It is only a couple blocks south of the river so Riverwalk and River North are close. The rooms are comfortable, and the staff is friendly.
Stayed 2 nights in Dec 2024

10/10 Excellent

Lindsay

Liked: Cleanliness, staff & service, property conditions & facilities
We loved the StayPineapple so much and can't wait to stay again! The location, the rooms, the staff, the beds, everything was amazing. And the VIEW was just insane. Highly recommend.
Stayed 7 nights in Dec 2024

10/10 Excellent

Alistair

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Staff was really nice and location can’t be beat
Stayed 2 nights in Dec 2024

8/10 Good

Elizabeth

Travelled with family
Liked: Cleanliness, staff & service, property conditions & facilities
Exceptionally clean and architecturally unique hotel. Google Chicago Reliance Building. Two things kept my review from being excellent: 1) the room could use updating: peeling wallpaper, dinged up and damaged furniture, peeling tile in the bathroom; 2) a few of the staff members were less than helpful but everyone else was great. All in all, I would definitely stay here again.
Stayed 3 nights in Dec 2024

6/10 Okay

Constance

Travelled with family
Liked: Cleanliness, staff & service
The room was very small and close to the elevators, one of which was very noisy and clunked against something every time it moved. So loud, it shook the room! We’ve stayed here many times, but this was by far the worst room. The front desk staff when we arrived was busy chatting with her boyfriend, and was fairly abrupt with us. Otherwise, the staff was terrific, as we’ve come to expect. Gracious and helpful.
Stayed 4 nights in Dec 2024

10/10 Excellent

Rodolfo

Travelled with family, Business traveller
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
I will definitely book at this hotel again.
Stayed 4 nights in Dec 2024

10/10 Excellent

Robert

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great location, staff, and room!!
Stayed 1 night in Dec 2024

10/10 Excellent

Justin, Morristown

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Easy check in and enjoyed the water bottle and filling station. Location is perfect for shopping and very close to the Blue Line and Red Line.
Stayed 1 night in Dec 2024

10/10 Excellent

Mindelyn

Liked: Cleanliness, property conditions & facilities
Great place in a great location
Stayed 1 night in Dec 2024

10/10 Excellent

Melissa

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Everyone was friendly and willing to help with the smallest things.
Stayed 2 nights in Dec 2024

8/10 Good

Lisa

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The hotel itself was wonderful. The staff was good. The restaurant inside the hotel was horrible. They only accepted reservations. They had us wait for a spot at the bar to eat but were not managing it and other people just skipped ahead of us. We ended up leaving and going elsewhere. The valet parking took a long time and was confusing at first.
Stayed 2 nights in Dec 2024

6/10 Okay

Kathleen

Travelled with family
Liked: Cleanliness, staff & service, property conditions & facilities
Disliked: Amenities
Hotel was great, but here are additional “amenities fees” added that are not well explained upfront. When we asked we were told it was for unlimited coffee in our room and cookies in the lobby.
Stayed 1 night in Dec 2024

10/10 Excellent

Patricia

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Lovely property near theaters and the river walk and lots of shopping and food! Already have reservations to come back! Staff were excellent!
Stayed 1 night in Dec 2024

10/10 Excellent

James

Nice place to stay
Stayed 1 night in Dec 2024

10/10 Excellent

Angel, Divernon

Travelled with family
Liked: Cleanliness, staff & service
Disliked: Property conditions & facilities
The hotel is very cute with all its decor. You are able to get a great nights sleep in the comfy beds. The only bad thing is the bathroom is small, and the bathroom door makes it hard to enter and exit.
Stayed 2 nights in Dec 2024

8/10 Good

Miguel

Stayed 5 nights in Nov 2024