Go back to search

Staypineapple, An Iconic Hotel, The Loop

$250
/ night

Avg. for October

Staypineapple, An Iconic Hotel, The Loop - Image 1
Staypineapple, An Iconic Hotel, The Loop - Room
Staypineapple, An Iconic Hotel, The Loop - Room
Staypineapple, An Iconic Hotel, The Loop - Reception
Staypineapple, An Iconic Hotel, The Loop - Bathroom

Prices for Staypineapple, An Iconic Hotel, The Loop

Select dates to see prices and availability

$250
/ night

Avg. for October

Monthly average prices

Nightly prices at Staypineapple, An Iconic Hotel, The Loop average $105 in January, the cheapest month, and $344 in September, the most expensive, based on the last 12 months.

Average nightly price at Staypineapple, An Iconic Hotel, The Loop by month, last 12 months (USD)
MonthAverage price
January$105
February$116
March$133
April$172
May$277
June$317
July$282
August$305
September$344
October$250
November$158
December$130

Most expensive: September (~$344)

Cheapest: January (~$105)

About this property

Take advantage of recreation opportunities such as a fitness center, or other amenities including tour/ticket assistance and a ballroom.
Show more
  • Parking

  • Non-Smoking Rooms

  • Valet Parking

  • Housekeeping

  • Banquet Facilities

  • Bicycle Rental

Show all

Location

1 West Washington, Theatre District, Chicago, Illinois, United States of America

State Street (0.1 miles)

Daley Plaza (0.1 miles)

Chicago Theatre (0.2 miles)

James M. Nederlander Theatre (0.2 miles)

Michigan Avenue (0.2 miles)

Goodman Theater (0.2 miles)


Room options

Atwood Queen

Room details

1 Queen Bed

Sleeps 2

Air Conditioning
Private Bathroom
Crib(s) (Free)

Atwithood Queen Mobility Accessible with Roll-In Showither

Room details

1 Queen Bed

Sleeps 2

Air Conditioning
Private Bathroom
Crib(s) (Free)

Reliance King Suite Mobility Accessible with Tub

Room details

1 King Bed
and
1 Sofa Bed

Sleeps 4

Air Conditioning
Private Bathroom
Crib(s) (Free)

Reliance King Suite

Room details

1 King Bed

Sleeps 4

Air Conditioning
Private Bathroom
Crib(s) (Free)

Burnham Twitho Double Mobility Accessible with Roll-In Showither

Room details

2 Full Beds

Sleeps 4

Air Conditioning
Private Bathroom
Crib(s) (Free)

Millennium Park View King Suite

Room details

1 King Bed

Sleeps 4

Air Conditioning
Private Bathroom
Crib(s) (Free)

Burnham 2 Two Queen

Room details

2 Queen Beds

Sleeps 4

Air Conditioning
Private Bathroom
Crib(s) (Free)

Burnham King

Room details

1 King Bed

Sleeps 2

Air Conditioning
Private Bathroom
Crib(s) (Free)

Atwithood Queen Mobility Accessible with Tub

Room details

1 Queen Bed

Sleeps 2

Air Conditioning
Private Bathroom
Crib(s) (Free)

Burnham Twitho Double Mobility Accessible with Tub

Room details

2 Full Beds

Sleeps 4

Air Conditioning
Private Bathroom
Crib(s) (Free)

Guest reviews of Staypineapple, An Iconic Hotel, The Loop

What guests think

AI-generated summary based on recent guest reviews

At Staypineapple, An Iconic Hotel, The Loop, guests repeatedly highlight the central Loop location, friendly staff, historic charm, and exceptionally comfortable beds, with many also noting clean rooms, nice city views, and convenient touches like refillable water bottles.

Read more

Facilities

Mixed

Cleanliness

Clean

Service

Friendly

Location

Central

Was this helpful?

6

Susan

IAN-logo

4 weeks ago

·

Stayed 4 nights

Street noise on the 15th floor horrible.
Street noise on the 15th floor horrible.

10

Vickie

IAN-logo

4 weeks ago

·

Stayed 4 nights

The location was excellent if you are looking for a city experience. I thought it was windy and realized I was hearing the el early in the morning. Beautiful historic architecture inside and out. The rain make a tinkling noise on the glazed ceramic tiles. Chicago windows!! A very short walk to the Bean and the Art Museum. We utilized public transportation/CTA. The el from the airport, 1/2 block away, major bus routes outside the door; the express bus to the south side and the bus to the Gold Coast. Tap-on Tap-off for $2.50. The room is well appointed and the duvet was lovely. Many hotels have reduced themselves to paper and plastic cups, Staypineapple had mugs and Bourbon Glasses!!! Extremely clean, great staff. We had a relaxed breakfast at the restaurant our last morning, very good food and friendly service. I wish we could have tried the Happy Hour Oysters. I would stay again!
The location was excellent if you are looking for a city experience. I thought it was windy and realized I was hearing the el early in the morning. Beautiful historic architecture inside and out. The rain make a tinkling noise on the glazed ceramic tiles. Chicago windows!! A very short walk to the Bean and the Art Museum. We utilized public transportation/CTA. The el from the airport, 1/2 block away, major bus routes outside the door; the express bus to the south side and the bus to the Gold Coast. Tap-on Tap-off for $2.50. The room is well appointed and the duvet was lovely. Many hotels have reduced themselves to paper and plastic cups, Staypineapple had mugs and Bourbon Glasses!!! Extremely clean, great staff. We had a relaxed breakfast at the restaurant our last morning, very good food and friendly service. I wish we could have tried the Happy Hour Oysters. I would stay again!

10

Wan Ting

IAN-logo

4 weeks ago

·

Stayed 1 night

Loved everything about this stay! The staff are so warm and welcoming, and the room decorations are adorable. The view from the window was another highlight for me. The location is perfect, with plenty of shopping nearby. I’ll definitely choose to stay here again on my next trip!
Loved everything about this stay! The staff are so warm and welcoming, and the room decorations are adorable. The view from the window was another highlight for me. The location is perfect, with plenty of shopping nearby. I’ll definitely choose to stay here again on my next trip!

6

Jacob

IAN-logo

4 weeks ago

·

Stayed 1 night

Overall the our stay at this property was just OK. A few things to account for: - The enhancements the offer such as guaranteed early check-in do not mean anything so do not waste your money. I paid for "guaranteed early check-in" which would allow us to arrive a noon. However when we arrived this was not the case, we need to wait an additional 3 hours before our "guaranteed early check-in" room was available. I called the night before to make sure this "enhancement" was included and I was assured it was. When asking the front desk they did not see it on my account, but informed me even if it was it is based on availability and not guaranteed. Also the website noted about a welcome drink of wine or beer, when asking the front desk they noted it was only wine. However the front desk did say we could grab a beer free of charge due to the wait. - The rooms while nice, showed signs of neglect. The bed frame was too large for the mattress so it stuck out into the walk way. I lost count how many times I banged my shin on it. Also the shower fixtures were loose and sticking out of the wall, it worked OK but seemed kind of janky. Several of the outlets were not working, which resulted in a dead phones when we woke up. - The valet took over 45 minutes to get our car, we even arrived well before the checkout time to avoid the rush. The valet was going as fast as he could, but I think the hotel should be aware of the extended wait and hire another valet for the weekends.
Overall the our stay at this property was just OK. A few things to account for: - The enhancements the offer such as guaranteed early check-in do not mean anything so do not waste your money. I paid for "guaranteed early check-in" which would allow us to arrive a noon. However when we arrived this was not the case, we need to wait an additional 3 hours before our "guaranteed early check-in" room was available. I called the night before to make sure this "enhancement" was included and I was assured it was. When asking the front desk they did not see it on my account, but informed me even if it was it is based on availability and not guaranteed. Also the website noted about a welcome drink of wine or beer, when asking the front desk they noted it was only wine. However the front desk did say we could grab a beer free of charge due to the wait. - The rooms while nice, showed signs of neglect. The bed frame was too large for the mattress so it stuck out into the walk way. I lost count how many times I banged my shin on it. Also the shower fixtures were loose and sticking out of the wall, it worked OK but seemed kind of janky. Several of the outlets were not working, which resulted in a dead phones when we woke up. - The valet took over 45 minutes to get our car, we even arrived well before the checkout time to avoid the rush. The valet was going as fast as he could, but I think the hotel should be aware of the extended wait and hire another valet for the weekends.

10

Edith

IAN-logo

Sep 10, 2026

·

Stayed 1 night

Super convenient location just 2 blocks from the train! The staff was amazing super helpful!
Super convenient location just 2 blocks from the train! The staff was amazing super helpful!

Property Policies

Check-in instructions

Everything you need to know for a smooth check-in.

Show more

Check-in

Check-out

From 16:00 to 00:00

Before 12:00


Good to know

Additional policies and info about this property.

Show more

Optional extras

Additional paid services you can request.

Show more

FAQs about Staypineapple, An Iconic Hotel, The Loop

Is parking available at the hotel?

Valet parking is available at the property for a fee of USD 75 per night. No reservation is required for parking.


Does the hotel allow pets?

Pets are allowed at the property with a fee of USD 29.95 per accommodation, per night. Service animals are exempt from fees.


What are the check-in and check-out times?

Check-in is at 16:00 and check-out is at 12:00. Early or late check-in/check-out may be available upon request, but additional charges may apply.

What accessibility features does the hotel offer?

The property has limited wheelchair accessibility, including features like step-free entrances and accessible public areas. However, specific details about room accessibility are not provided.


Where is the hotel located in relation to key landmarks?

The hotel is centrally located in Chicago, just a 5-minute walk from the Chicago Cultural Center and City Hall. It is 0.4 miles from the Chicago Riverwalk and 0.5 miles from the Art Institute of Chicago.


What are the hotel's policies for guests staying with children?

Children are allowed at the property, and there is no specified minimum age for kids to stay for free.


Have a question?

Instant AI responses are based on hotel information


Considering this hotel for your Chicago trip?

What do room rates usually run at Staypineapple, An Iconic Hotel, The Loop in Chicago?

Over the next 60–90 days, room rates at Staypineapple, An Iconic Hotel, The Loop in Chicago typically land around $221 a night for two guests, ranging from $188 to $346 on peak dates.


Why is Staypineapple, An Iconic Hotel, The Loop so affordable?

Staypineapple, An Iconic Hotel, The Loop in Chicago undercuts 17 of 20 comparable hotels nearby, while similar properties typically run around $279 a night. The hotel’s downtown Cook County location — a short walk from Michigan Avenue and Millennium Park — and its appeal to couples and business travellers help explain why it sits below the neighborhood median.

When can I find the lowest room rates at Staypineapple, An Iconic Hotel, The Loop in Chicago?

January is the cheapest month to stay at Staypineapple, An Iconic Hotel, The Loop in Chicago, averaging $150 a night; June is the priciest month, averaging $402.


How does the nightly price at Staypineapple, An Iconic Hotel, The Loop in Chicago compare to recent weeks?

The current price at Staypineapple, An Iconic Hotel, The Loop in Chicago is $407 per night for 2 guests, which is high for this hotel: about 15% above its $358 average over the last 60 days. Most nights over that period fell between $195 and $877.

Prices for upcoming dates

October 2026
November 2026

Cheaper

Pricier

Average nightly price across deals, with taxes & fees.

Prices in USD for 2 guests, updated daily.



Product

  • Affiliate program
  • Cookie preferences
  • Cookie policy
  • Privacy policy
  • Terms of use

Social


© 2026 Vio