Stay Realm Logo

Discover

Hotels

Settings

Currency
Language
Loading...
9 / 10 Guest Rating

Staypineapple, An Iconic Hotel, The Loop

1 West Washington, Chicago, us

Staypineapple, An Iconic Hotel, The Loop - main view

About the Property

Historic Architecture and Luxury Design
Experience the grandeur of historic Chicago architecture at Staypineapple, An Iconic Hotel, The Loop. Designed by renowned architect Daniel Burnham, the hotel boasts mosaic floors and marble ceilings, offering a luxurious stay in the heart of Chicago's Loop.

Modern Amenities and Stunning Views
Indulge in the perfect blend of classic elegance and modern comfort in our rooms. Enjoy white and gray decor with mahogany furnishings, flat-screen TVs, and plush bedding. Upgrade to a suite for breathtaking views of Millennium Park and Lake Michigan.

Convenient Location and Special Amenities
Explore Chicago's top attractions with ease - from shopping on Michigan Avenue to visiting Millennium Park. Take advantage of our fitness center, bicycle rental service, and special perks for your furry friends. Don't miss out on experiencing Navy Pier and other nearby entertainment venues during your stay.

Book now for an unforgettable stay at Staypineapple, An Iconic Hotel, The Loop!

Facilities & Amenities

Fitness facilities
WiFi available
Free WiFi
Parking
Non-smoking rooms
Air conditioning
Fitness center
24-hour front desk
Heating
Pets allowed

Important Information

Check-in & Out

Check-in
Check-out12:00 PM

Property Notes

Reservations for 10 rooms or more need to be contracted as a Group with the hotel directly.Guests are required to show a photo ID and credit card upon check-in. Please note that all Special Requests are subject to availability and additional charges may apply. A deposit may be required at the property.

Check Room Availability

1 night · 2 adults

Available Rooms

Deluxe King Room - Photo 1
Deluxe King Room - Photo 2
Deluxe King Room - Photo 3
Deluxe King Room - Photo 4
1/4

Deluxe King Room

Complete with luxury bedding and linens, this room includes a 50-inch flat-screen HDTV, complimentary bottled water, a small refrigerator and a Keurig coffee maker.

17 sqm
Sleeps 2
1 Extra-large double bed (Super-king size) (181-210 cm wide)
Amenities
Coffee/tea makerShowerSafety deposit boxHair dryerRefrigeratorDesk

Deluxe King

Non-refundable
Room Only
20% OFF$254.24

$203.39

Includes taxes & fees
Millennium Park King Suite - Photo 1
Millennium Park King Suite - Photo 2
Millennium Park King Suite - Photo 3
Millennium Park King Suite - Photo 4
Millennium Park King Suite - Photo 5
Millennium Park King Suite - Photo 6
1/6

Millennium Park King Suite

Featuring iconic views of Millennium Park and Lake Michigan, this suite offers a separate living room with a sofa bed.

37 sqm
Sleeps 4
1 Extra-large double bed (Super-king size) (181-210 cm wide)
Amenities
Coffee/tea makerShowerSafety deposit boxHair dryerRefrigeratorDesk

Millennium Park King Suite

Non-refundable
Room Only
20% OFF$542.36

$433.89

Includes taxes & fees
Executive King Suite - Disability Access - Photo 1
Executive King Suite - Disability Access - Photo 2
Executive King Suite - Disability Access - Photo 3
Executive King Suite - Disability Access - Photo 4
Executive King Suite - Disability Access - Photo 5
1/5

Executive King Suite - Disability Access

This handicap-accessible suite features a separate living room with a sofa bed, along with luxury bedding and linens.

37 sqm
Sleeps 4
1 Extra-large double bed (Super-king size) (181-210 cm wide)
1 Sofa bed (Variable Size)
Amenities
Coffee/tea makerSafety deposit boxHair dryerRefrigeratorDeskSeating Area

Mobility Accessible Executive King Suite with Tub

Non-refundable
Room Only
20% OFF$433.13

$346.5

Includes taxes & fees
Deluxe Queen Room with Two Queen Beds - Photo 1
Deluxe Queen Room with Two Queen Beds - Photo 2
Deluxe Queen Room with Two Queen Beds - Photo 3
Deluxe Queen Room with Two Queen Beds - Photo 4
1/4

Deluxe Queen Room with Two Queen Beds

Complete with luxury bedding and linens, this room includes a 50-inch flat-screen HDTV, complimentary bottled water, a small refrigerator and a Keurig coffee maker.

16 sqm
Sleeps 4
2 Queen bed (151-180 cm wide)
Amenities
Coffee/tea makerShowerSafety deposit boxHair dryerRefrigeratorDesk

Deluxe Two Queens

Non-refundable
Room Only
20% OFF$292.56

$234.05

Includes taxes & fees
Deluxe Queen Mobility Accessible w/Roll-in Shower - Photo 1
Deluxe Queen Mobility Accessible w/Roll-in Shower - Photo 2
Deluxe Queen Mobility Accessible w/Roll-in Shower - Photo 3
Deluxe Queen Mobility Accessible w/Roll-in Shower - Photo 4
1/4

Deluxe Queen Mobility Accessible w/Roll-in Shower

The double room offers a flat-screen TV with streaming services, a tea and coffee maker, a safe deposit box and heating. The unit offers 1 bed.

16 sqm
Sleeps 2
1 Queen bed (151-180 cm wide)
Amenities
Coffee/tea makerShowerSafety deposit boxHair dryerRefrigeratorDesk

Accessible Queen with Roll-In Shower

Non-refundable
Room Only
20% OFF$243.1

$194.48

Includes taxes & fees
Deluxe Queen Mobility Accessible w/Tub - Photo 1
Deluxe Queen Mobility Accessible w/Tub - Photo 2
Deluxe Queen Mobility Accessible w/Tub - Photo 3
Deluxe Queen Mobility Accessible w/Tub - Photo 4
1/4

Deluxe Queen Mobility Accessible w/Tub

This double room features a tea and coffee maker, a safe deposit box and a flat-screen TV with streaming services. The unit offers 1 bed.

16 sqm
Sleeps 2
1 Queen bed (151-180 cm wide)
Amenities
Coffee/tea makerSafety deposit boxHair dryerRefrigeratorDeskBottle of water

Accessible Queen with Grab Bar Bathtub

Non-refundable
Room Only
20% OFF$241.46

$193.17

Includes taxes & fees
Reliance King Suite - Photo 1
Reliance King Suite - Photo 2
Reliance King Suite - Photo 3
Reliance King Suite - Photo 4
Reliance King Suite - Photo 5
Reliance King Suite - Photo 6
Reliance King Suite - Photo 7
1/7

Reliance King Suite

1 King BedLayout - Bedroom Entertainment - 50-inch LCD TV with premium channels, streaming services, iPod dockSleep - Pillowtop bed, premium bedding, a down duvet, turndown service, and bed sheets Bathroom - Private bathroom, shower/tub combination, bathrobes, and designer toiletriesPractical - Laptop-compatible safe, free newspaper, and iron/ironing board; cribs (free) available on requestComfort - Climate-controlled air conditioningNeed to Know - Housekeeping on requestNon-SmokingConnecting/adjoining rooms can be requested, subject to availability

Sleeps 4
1 King bed (151-180 cm wide)
Amenities
TelephoneHair dryerBathrobeDeskPrivate bathroomInterconnected room(s) available

Reliance King Suite

Non-refundable
Room Only
20% OFF$327.22

$261.78

Includes taxes & fees
Reliance King Suite Mobility Accessible w/Tub - Photo 1
Reliance King Suite Mobility Accessible w/Tub - Photo 2
Reliance King Suite Mobility Accessible w/Tub - Photo 3
Reliance King Suite Mobility Accessible w/Tub - Photo 4
Reliance King Suite Mobility Accessible w/Tub - Photo 5
1/5

Reliance King Suite Mobility Accessible w/Tub

1 Double Sofa Bed and 1 King BedLayout - Bedroom Entertainment - 50-inch LCD TV with premium channels, streaming services, iPod dockSleep - Pillowtop bed, premium bedding, a down duvet, turndown service, and bed sheets Bathroom - Private bathroom, shower/tub combination, bathrobes, and designer toiletriesPractical - Laptop-compatible safe, free newspaper, and iron/ironing board; cribs (free) available on requestComfort - Climate-controlled air conditioningAccessibility - Wheelchair accessibleNeed to Know - Housekeeping on requestNon-SmokingConnecting/adjoining rooms can be requested, subject to availability

Sleeps 4
1 Sofa bed (131-150 cm wide)
1 King bed (151-180 cm wide)
Amenities
TelephoneHair dryerBathrobeDeskPrivate bathroomInterconnected room(s) available

Reliance King Suite Mobility Accessible w/Tub

Non-refundable
Room Only
20% OFF$327.22

$261.78

Includes taxes & fees
Burnham 2 Two Queen - Photo 1
Burnham 2 Two Queen - Photo 2
Burnham 2 Two Queen - Photo 3
Burnham 2 Two Queen - Photo 4
Burnham 2 Two Queen - Photo 5
1/5

Burnham 2 Two Queen

2 Queen BedsEntertainment - 50-inch LCD TV with premium channels, streaming services, iPod dockSleep - Pillowtop bed, premium bedding, a down duvet, turndown service, and bed sheets Bathroom - Private bathroom, shower/tub combination, bathrobes, and designer toiletriesPractical - Laptop-compatible safe, free newspaper, and iron/ironing board; cribs (free) available on requestComfort - Climate-controlled air conditioningNeed to Know - Housekeeping on requestNon-SmokingConnecting/adjoining rooms can be requested, subject to availability

Sleeps 4
2 Queen Bed (150-160 cm wide)
Amenities
TelephoneHair dryerBathrobeDeskPrivate bathroomInterconnected room(s) available

Burnham Two Queen

Non-refundable
Room Only
20% OFF$270.61

$216.49

Includes taxes & fees
Millennium Park View King Suite - Photo 1
Millennium Park View King Suite - Photo 2
Millennium Park View King Suite - Photo 3
Millennium Park View King Suite - Photo 4
Millennium Park View King Suite - Photo 5
1/5

Millennium Park View King Suite

1 King BedLayout - Bedroom Entertainment - 50-inch LCD TV with premium channels, streaming services, iPod dockSleep - Pillowtop bed, premium bedding, a down duvet, turndown service, and bed sheets Bathroom - Private bathroom, shower/tub combination, bathrobes, and designer toiletriesPractical - Laptop-compatible safe, free newspaper, and iron/ironing board; cribs (free) available on requestComfort - Climate-controlled air conditioningNeed to Know - Housekeeping on requestNon-SmokingConnecting/adjoining rooms can be requested, subject to availability

Sleeps 4
1 King bed (151-180 cm wide)
Amenities
TelephoneHair dryerBathrobeDeskPrivate bathroomInterconnected room(s) available

Millenium Park View King Suite

Non-refundable
Room Only
20% OFF$612

$489.6

Includes taxes & fees
Burnham King - Photo 1
Burnham King - Photo 2
Burnham King - Photo 3
Burnham King - Photo 4
Burnham King - Photo 5
1/5

Burnham King

1 King BedEntertainment - 50-inch LCD TV with premium channels, streaming services, iPod dockSleep - Pillowtop bed, premium bedding, a down duvet, turndown service, and bed sheets Bathroom - Private bathroom, shower/tub combination, bathrobes, and designer toiletriesPractical - Laptop-compatible safe, free newspaper, and iron/ironing board; cribs (free) available on requestComfort - Climate-controlled air conditioningNeed to Know - Housekeeping on requestNon-SmokingConnecting/adjoining rooms can be requested, subject to availability

Sleeps 3
1 King bed (151-180 cm wide)
Amenities
TelephoneHair dryerBathrobeDeskPrivate bathroomInterconnected room(s) available

Burnham King

Non-refundable
Room Only
20% OFF$236.64

$189.31

Includes taxes & fees

Guest Reviews

9
Exceptional1590 verified reviews
AI Summary

Guests highly rate the excellent location and frequently praise the friendly staff.

Categories

Cleanliness8.9
Service9.4
Location9.9
Room Quality8.8
Amenities8.4
Value for Money8.3
Food and Beverage8.9
Overall Experience9.4

Select topics to read reviews

I
Inspire41364317527ANN ARBOR, MICHIGAN
Verified booking
Family
Standard Room
Stayed in Apr 11, 2026

"Pineapples mean Welcome!"

10.0

Fantastic stay. Darnell heldour lu before and after check in/out. We loved the water bar! e

Helpful?
K
KellyusUS
Verified booking
solo_traveller
Standard Room
Stayed in Apr 11, 2026

"Very Good"

7.0
Helpful?
P
Petra-AlexandrachCH
Verified booking
extended_group
Standard Room
Stayed in Apr 9, 2026

"Würde es wieder wählen. Sobald das Restaurant/Empfang neu fertiggestellt wurden. War z.Z. im Umbau."

8.0

Kuschliges Bett. Lage vom Hotel.

bessere Kosmetkprodukte im Bad. Eine Lampe mehr.

Helpful?
V
VallacibrBR
Verified booking
couple
Standard Room
Stayed in Apr 8, 2026

"Exceptional"

10.0
Helpful?
I
IndianaNif
Verified booking
Couples
Standard Room
Stayed in Apr 4, 2026

"Warm welcoming and fun for downtown"

10.0

My husband and I stayed for a night to go see a concert downtown, and Staypineapple Chicago was *perfect* and exceeded our expectations. Immediately at check in, staff was warm and welcoming, and the amenities are stellar. Being able to enjoy a complimentary drink and treat upon arrival was a welcome touch. And later on at night when we returned to our room from cold and rain, William at the front desk helped ensure we had what we needed to stay comfortable and to feel cared for during the rest of our stay. The hotel was incredibly clean and comfortable—even the comforters are freshly laundered duvets which is a big deal for me as someone who dreads the typical gnarly looking comforters at hotels. And the fun decor and kitsche-y flare in a beautiful boutique space was lovely. We will definitely be back and recommend to friends!

Helpful?
M
MarlausUS
Verified booking
couple
Standard Room
Stayed in Apr 3, 2026

"Exceptional"

10.0
Helpful?
K
KevingbGB
Verified booking
couple
Standard Room
Stayed in Apr 2, 2026

"Exceptional"

10.0

Great location and comfy bed.

Helpful?
D
De OvandomxMX
Verified booking
couple
Standard Room
Stayed in Mar 31, 2026

"Exceptional"

10.0
Helpful?
A
AbrilarAR
Verified booking
couple
Standard Room
Stayed in Mar 28, 2026

"Exceptional"

10.0
Helpful?
N
nicolinat185
Verified booking
Friends getaway
Standard Room
Stayed in Mar 24, 2026

"Excellent experience"

10.0

We stayed on Sat March 14th. Centrally located within the theater district. We also saw the river being dyed for St. Patrick's Day and did the architectural boat tour. Everything was within easy walking distance. We received excellent service from Sashon & DJ who were very friendly and went above and beyond to make us feel welcome. They were very accommodating not only to us, but as I was waiting in line, I witnessed them helping other customers with directions and suggestions to local attractions. This is the 2nd time we have stayed when seeing a show, and this is our go to when staying in the theater district. Rooms are very clean, with great views of the city. Beds are very comfortable. Will definitely stay again.

Helpful?