FREQUENTLY ASKED QUESTIONS

If you're arriving by plane from O'Hare International Airport (ORD):

• Traveling by car: Take I-190 E and merge onto I-90 E toward downtown Chicago. Continue about 14 miles, then take exit 51C for Washington Boulevard. Turn left on Washington, then turn right on Dearborn Street.
• Traveling via public transit (CTA Train): Take CTA Blue Line train toward Forest Park. Exit at the Washington Station stop in the Loop. From there, walk east on Washington Street for about 2 blocks to 1 W. Washington Street.

If you're arriving by plane from Midway Airport (MDW): 

• Traveling by car: Take S Cicero Avenue north to merge onto I-55 N toward Chicago. Continue on I-55 N for about 10 miles, then take the exit for Congress Parkway / I-290 E toward downtown. Follow I-290 E for about 3 miles, then take the exit for Clinton Street. Turn left onto Clinton Street, then right onto Washington Street.
• Traveling via public transit (CTA Train): Take the CTA Orange Line train toward the Loop / downtown Chicago. Exit at the Washington/Wells stop in the Loop. From there, walk east on Washington Street for about 2 blocks to 1 W. Washington Street.

Staypineapple Chicago offers valet parking for guests. Overnight valet parking is $75 including taxes and includes unlimited in-and-out access. For shorter visits, there are also hourly rates available. Additionally, a special rate of $18 applies for guests dining or attending events at Atwood.

Staypineapple Chicago does not offer shuttle service, but getting around is easy! We're conveniently located within walking distance of popular attractions like Millennium Park and the Chicago Theatre District, so you don’t need to worry about driving or parking. We're also ideally located near public transit, including CTA “L” trains and bus lines and rideshare services like Uber and Lyft are readily available in the area.

Staypineapple Chicago is located near several CTA “L” train stations, just a short walk away, including Washington/Wells (about 2 blocks, a 5-minute walk) and Clark/Lake (about 5 blocks, a 10-minute walk), providing easy access to top attractions like the Art Institute of Chicago, Grant Park and the Chicago Riverwalk. The trains also make it simple to explore neighborhoods beyond the Loop, including Lincoln Park, Wicker Park and Chinatown.

Staypineapple Chicago is conveniently located near two major airports. O’Hare International Airport (ORD) is about 17 miles northwest of downtown Chicago, while Midway International Airport (MDW) is roughly 11 miles southwest.

In consideration of all our guests, check-in is after 4:00 PM and check-out is at 12:00 PM. Staypineapple Chicago also offers guaranteed early check-in or late check-out for an additional fee. Just let us know in advance, and we'll do our best to accommodate your request based on availability.

We’d be happy to store your luggage at the front desk while you wait for your room to be ready, or after you’ve checked out if you’d like to explore a bit more before departing.

The amenities included in your stay have you covered from check-in to check-out. Start with a complimentary CORE Welcome Drink, then enjoy some Afternoon Delights of pineapple cookies and coffee. Explore the city on our Pineapple Bikes and stay hydrated with our refillable PATH water bottles. End your day in cozy double duvets with our Naked Experience, then wake up refreshed with in-room coffee and tea. Do we even need to mention the high-speed WiFi and all your favorite streaming shows right on your TV? Yes, we've thought of everything so you don't have to.

Staypineapple Chicago is more than pet-friendly, we're pet-obsessed! Dogs, cats, pigs — you name it — we roll out the red carpet so your furry (or feathery) travel companion can enjoy the stay too. We also make it easy to save on your pet’s stay with our Pineapple Pup Package! Get 50% off the pet fee plus fun treats and goodies for your cuddly pal.

Let's set the record straight! Staypineapple Chicago and every Staypineapple hotel is family-friendly, making every stay comfortable and enjoyable for kids, adults and everyone in between.

Our fitness center is open 24 hours a day, so you can squeeze in a workout whenever you like… unless, of course, you’d rather hit snooze and skip it.

Our in-house restaurant, Atwood, located on the first floor of Staypineapple Chicago, serves familiar favorites created with the finest local ingredients. It’s open Monday-Friday, 7:00 AM to 9:00 PM and Saturday-Sunday, 9:00 AM to 9:00 PM, with breakfast daily until 11:00 AM and weekend brunch until 2:00 PM. Enjoy Pineapple Hour (happy hour, but better), at the bar daily from 4:00 to 6:00 PM. For the full menu and more information, visit Atwood’s website.

Also, if those emergency snack cravings hit, don’t worry — you can grab something from our Quick Bites & Bevvies anytime, day or night. 

Staypineapple Chicago offers five ADA-accessible room types to ensure a comfortable stay for all guests. Options include the Atwood Queen with a roll-in shower or tub, the Burnham Two Double with a roll-in shower or tub and the Reliance King Suite with a tub. All rooms feature mobility-friendly amenities designed to provide a safe and enjoyable stay.

We offer dry cleaning services during your stay. Just ask one of our Everything People about pick-up and drop-off times, and consider your clothes magically refreshed.

Every room comes with a mini fridge, perfect for keeping snacks and drinks chilled. While there’s no freezer, it’s ideal for storing beverages, leftovers or any treats you pick up around the city.

Staypineapple Chicago offers adjoining rooms, though availability is limited and cannot be guaranteed. To book, email [email protected] or call (866) 866-7977, and we’ll do our best to accommodate your request.

Staypineapple offers two meeting spaces for events or business gatherings. The Burnham Room accommodates up to 50 guests, while our restaurant, Atwood, can host up to 125 guests. To book a space, email [email protected] or call (206) 823-3903. For more information, visit our Groups page.

Our restaurant, Atwood, offers to-go orders delivered to your room daily from 7:00 AM to 9:00 PM. Just browse the menu and call 312-368-1900 or dial 3526 from your room to place an order — and voilà, deliciousness delivered right to you! 

Staypineapple customer service is just an email or phone call away at [email protected] or (866) 866-7977. One of our friendly team members will be happy to help make your day a little sweeter!

While we don't have a traditional (and let's be real, boring) loyalty program, we have something 10 times better. The CORE gives members the lowest rates at any Staypineapple hotel, plus instant savings, exclusive offers and special packages that make every stay sweeter. Learn more and join The CORE today!

Whether it’s a wedding, family reunion, business event, or any reason to gather, Staypineapple Chicago offers group rates that make it easy for everyone to stay together. To book your group, email [email protected] or call (206) 823-3903. For more information, visit our Groups page.

Booking direct with Staypineapple gets you the lowest rates you won't find on the big online travel sites. By skipping the high fees charged to us by “the usual suspects,” we pass those savings straight to you! Even better? When you join The CORE, you'll unlock the lowest rates, exclusive offers and special packages... because who doesn’t love a sweet deal?

At check-in, your debit or credit card will be authorized for your room charges, taxes, and a $50 incidental hold per day of your stay. Room charges and taxes are typically processed at check-out, while any unused incidental hold may remain on your account for up to 21 days depending on your bank. If you choose the Seal the Sweet Deal rate when booking, you can lock in our lowest rates and pay the full room amount and taxes at the time of booking, so you don’t have to worry about it when you arrive.

Illionois residents get 20% off their stay when they show a state-issued ID at check-in. Turn your everyday routine into the ultimate staycation! Book now to snag your discount. 

Staypineapple, Chicago is located in the heart of the Loop, putting you close to everything for your Chicago adventure. We’re just a few blocks, or a 6-minute walk, from Millennium Park and the iconic Cloud Gate (“The Bean”). You’ll also find top theatres within walking distance, including the Chicago Theatre and CIBC Theatre, perfect for catching popular Broadway shows, plays and concerts. For a Cubs baseball game or a concert at Wrigley Field, it’s just a 22-minute ride on the L train from Lake Station.

The Chicago Theatre is just north of the hotel, a convenient 4-minute walk that gets you to your show on time with minutes to spare. Pro tip: reserve a table at our in-house restaurant, Atwood, for the perfect pre- or post-show meal.