Reservations
Looking for that special place for a show-stopping event or sleek downtown business meeting? Look no further because booking groups, meetings and events at Staypineapple Chicago is a breeze! Staypineapple provides personalized attention along with a private space ideally tailored to your business meeting, company retreat, family reunion… really, any reason to party or put business minds together.
Ready to get started? Contact us for group bookings!
The Loop is the heart of downtown Chicago, and Staypineapple puts your group right in the center of it all. You'll be within walking distance of Chicago Union Station for easy arrivals, just a short ride from both Midway and O'Hare International Airports, and steps from the city's iconic architecture, renowned dining, theaters, and riverfront attractions.
For conference and convention groups, the hotel's location is a major advantage. Just minutes from McCormick Place and close to many downtown meeting venues, your team can enjoy the charm of a historic boutique hotel instead of a standard convention property while still getting to meetings, networking events, and the show floor with ease.
Make it easy for your favorite people to stay close to the celebration! Whether you’re planning a destination wedding, welcoming out-of-town guests, or simply want everyone together for the weekend, Staypineapple makes wedding room blocks refreshingly simple. With comfortable rooms, playful personality, and outstanding locations, we’ll help you create a convenient home base for your guests!
Simply fill out the form below and you’ll receive a custom booking link for your special day. No rooming lists, no cutoff dates to worry about, just an easy-to-share link and awesome discounted rates!
Our reservations team is available to help book your small group. Just give us a call at 1-866-866-7977, option 3. CALL NOW
That’s where our group services team comes in. We’ll work with you to lock in competitive rates, coordinate arrival logistics, and make sure your group has everything they need from check-in to checkout. Request a quote below and we’ll be in touch. REQUEST A QUOTE
With our dedicated Group Services team at your service, planning your next meeting or event at Staypineapple Chicago is a breeze!
Complete the form below, and we'll be back in touch shortly with all of the information you need to book your group with Staypineapple.