First rate comfort & style in the Second City

Staypineapple Chicago

Whether it’s a warm, summer day or a teeth-chattering winter white-out, Staypineapple Chicago will make every day a spectacular one. All of our rooms and suites feature historic touches original to the building while also offering every modern amenity: high-definition TVs, high-speed Wi-Fi and mini fridges. It’s your Windy City oasis.

(Not So) Standard Rooms

Deluxe Queen

The perfect package of historic charm and modern luxury, ideal for the solo traveler or the couple on-the-go.

  • Furnished with 1 Queen sized bed
  • Accommodates up to 2 guests

Deluxe Two Queen

Bring a friend (or two) and use this ideal room as a home base for all of your Chicago adventures.

  • Furnished with 2 Queen sized beds
  • Accommodates up to 4 guests

Deluxe King

Large and in charge, our Deluxe King room is tastefully decorated and comes with a host of royal amenities.

  • Furnished with 1 King sized bed
  • Accommodates up to 2 guests

Suites

Executive King Suite

Spacious and elegantly furnished, our Executive King Suite boasts a stylish private living room in addition to a lush king bed.

  • Furnished with 1 King bed
  • Accommodates up to 4 guests
  • Features a separate sleeper sofa
  • Relax in your own separate living room

Millennium Park View King Suite

Marvel at views of Millennium Park and Lake Michigan while enjoying amenities like an HDTV and a separate sitting room.

  • Furnished with 1 King sized bed
  • Accommodates up to 4 Guests
  • Features separate sleeper sofa
  • Relax in your own separate living room
  • Enjoy views of Millennium Park & Lake Michigan 

Accessible Rooms

Deluxe Queen Mobility Accessible w/ Roll-in Shower

The perfect package of historic charm and modern luxury, ideal for the solo traveler or the couple on-the-go. Includes added mobility features and a roll-in shower.

  • Furnished with 1 Queen sized bed
  • Accommodates up to 2 guests
  • Mobility accessible room with roll-in shower

Deluxe Queen Mobility Accessible w/ Tub

The perfect package of historic charm and modern luxury, ideal for the solo traveler or the couple on-the-go. Includes added mobility features and bathtub.

  • Furnished with 1 Queen sized bed
  • Accommodates up to 2 guests
  • Mobility accessible room with tub

Deluxe Two Double Mobility Accessible w/ Roll-in Shower

Bring a friend (or two) and use this ideal room as a home base for all of your Chicago adventures. Includes added mobility features and roll-in shower.

  • Furnished with 2 Double sized beds
  • Accommodates up to 4 guests
  • Mobility accessible room with roll-in shower

Deluxe Two Double Mobility Accessible w/ Tub

Bring a friend (or two) and use this ideal room as a home base for all of your Chicago adventures. Includes added mobility features and a bathtub.

  • Furnished with 2 Double sized beds
  • Accommodates up to 4 guests
  • Mobility accessible room with tub

Executive King Suite Mobility Accessible w/ Tub

Spacious and elegantly furnished, our Executive King Suite boasts a stylish private living room in addition to a lush king bed. Also includes added mobility features and a bathtub.

  • Furnished with 1 King bed
  • Accommodates up to 4 guests
  • Features a separate sleeper sofa
  • Relax in your own separate living room
  • Mobility accessible room with tub