Venue photo 1

Staypineapple, An Iconic Hotel, The Loop Chicago

4.6(2,302)
Hotel

About

Staypineapple Chicago, An Iconic Hotel, is set in a National Historic Landmark skyscraper from 1895, blending classic architecture with modern style. Located in the Loop, it offers easy access to Millennium Park, the Theatre District, and the Art Institute, making it ideal for business travelers wanting to explore downtown between meetings.

The hotel features well-maintained rooms with city or lake views, a small American dining spot, and a gym. Its attentive staff and thoughtful touches like filtered water stations and afternoon cookies create a welcoming atmosphere. Valet parking and bike rentals add convenience for guests attending nearby events or conferences.

Best for

  • Downtown Chicago multi-night stays
  • Client dinners near Millennium Park
  • Executive offsites with boutique style

Request a Package

Tell the venue what you're planning and they'll respond with a custom proposal within 1–2 business days.

Group Meeting

Custom request

Professional meeting space for your team — whether it's a meeting, training, workshop, or multi-day offsite. Half-day, full-day, or multi-day — with the option to request AV, catering, and your preferred room layout.

What's typically included

  • Meeting room & layout
  • Food & beverage
  • AV & technology

Room Block

Custom request

Reserve a block of rooms for your group — ideal for multi-day conferences, offsites, or any event where attendees are traveling from out of town.

What's typically included

  • Reserved guest rooms for your group
  • Flexible check-in & check-out dates
  • Negotiated group rates

Meeting + Room Block

Custom request

Bundle your meeting space and guest rooms in one request — perfect for multi-day offsites and conferences where the team meets by day and stays overnight.

What's typically included

  • Meeting room & layout
  • Food & beverage
  • AV & technology
  • Reserved guest rooms for your group

Venue Details

Standout features

National Historic Landmark building from 1895
Historic Architecture
National Historic Landmark building from 1895
Housed in a beautifully preserved 1895 skyscraper, the hotel offers a distinctive historic setting in the heart of Chicago’s Loop, blending classic architecture with modern style.
Steps from Millennium Park and the Theatre District
Location
Steps from Millennium Park and the Theatre District
Situated in the Loop, the hotel provides immediate access to major cultural attractions like Millennium Park, the Art Institute, and Chicago’s Theatre District, making it ideal for business guests wanting a central, walkable location.
Stylish rooms with lake or city views and deluxe amenities
Modern Comforts
Stylish rooms with lake or city views and deluxe amenities
Rooms blend modern design with comfort, offering features like in-room refrigerators, excellent beds, and some with views of Lake Michigan or the Chicago Theatre sign, complemented by amenities such as a gym and American dining on-site.

At a glance

Rated 4.6 on Google · 2,302 reviews