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View of the two queen beds in the Deluxe Two Queen bedroom

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.

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 Double 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 Double 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