YOUR GUIDE TO THE HOLIDAYS IN STAYPINEAPPLE CITIES
The holiday season is bringing plenty of reasons to celebrate in our favorite Staypineapple cities! From festive markets and dazzling light displays to can’t-miss theatre performances and seasonal traditions, there's something for everyone to enjoy. Plus, with holiday-themed room upgrades at select hotels, you can bring a little extra magic to your getaway. Here's what's happening this season!
Chicago: Markets, Lights and Holiday Theatre
Photo by Rezal Scharfe on Unsplash
Christkindlmarket: Shop handcrafted gifts, enjoy traditional German treats and experience the holiday magic at Chicago's beloved Christkindlmarket, November 20–December 24, 2026 at Daley Plaza, just a two-minute walk from Staypineapple Chicago. Book with promo code CHRISTKINDL to receive a complimentary collector's mug from this year's market!
Make It a Whoville Theatre Night: Staypineapple Chicago puts you right in the heart of the Theatre District, less than a five-minute walk from several major theatres, including the James M. Nederlander Theatre, where Dr. Seuss' How the Grinch Stole Christmas! The Musical plays December 9–27, 2026. Before the show, enjoy Mariela's prix fixe menu and theatre-themed cocktails right inside the hotel. Then, keep the Grinchy fun going with our Grinch's Whoville Hideaway room upgrade, featuring festive green decor, holiday-inspired touches and a special “Heart Grew Three Sizes” Cookie crafted by Mariela. Available in a suite or two-queen standard room. Click here to learn more and book your upgrade!
Millennium Park: Catch Chicago's official Christmas tree lighting on Saturday, November 21 at Millennium Park, just a fast five-minute walk from the hotel. The tree will remain illuminated through January 10, 2027. You can also enjoy ice skating at the McCormick Tribune Ice Rink, open daily November 20, 2026–January 31, 2027.
Click here to discover even more Chicago holiday happenings and festive bars serving up merry little sips all season long!
Boston: Holiday Markets and Ballet
Beacon Hill Boston | Photo by Andrew Spencer via Unsplash
Make It a Nutcracker Getaway: Enjoy the Boston Ballet's timeless holiday production of The Nutcracker at Citizens Opera House, approximately a quick 10-minute drive or 13-minute ride on the MBTA Orange Line from Staypineapple Boston. Whether you're planning a night at the ballet or simply want to add a little extra holiday magic to your stay, our Nutcracker Wonderland room upgrade brings the festivities right to your room with Nutcracker-inspired decor and seasonal touches. Click here to learn more and book your upgrade!
Snowport Holiday Market: Explore more than 125 local makers, seasonal food and drinks, custom cocktail bars, live music and festive decorations at Boston's Snowport Holiday Market in the Seaport neighborhood, less than a 15-minute drive from Staypineapple Boston.
Charles Dickens' A Christmas Carol: Step into Victorian England and rediscover the heart and soul of the holiday season with this timeless story at Emerson's Cutler Majestic Theatre, December 11–20, 2026. The theatre is just a short 12-minute walk from Staypineapple Boston.
Seattle: Christmas Markets and Neighborhood Traditions
Seattle Christmas Market: Discover European sweets, seasonal treats and handcrafted treasures at the Seattle Christmas Market at Seattle Center, less than a 10-minute walk from The Maxwell Hotel. Take a peek at how Taryn spent last year's holiday season exploring the magical market and enjoying a festive stay at the hotel!
Westlake Park: Join the holiday tree lighting celebration on November 27, 2026, featuring family-friendly crafts, costumed characters and sweet treats at Westlake Park, less than a 10-minute walk from Hotel FIVE. The main event begins at 5 p.m. with the lighting of the holiday tree and star, followed by fireworks. A holiday carousel will also be open November 27, 2026–January 3, 2027.
Candy Cane Lane: A Seattle tradition since the 1940s, the Ravenna neighborhood in the University District transforms into a festive display of holiday lights and decorations December 5, 2026–January 1, 2027. The magical experience is less than a 10-minute drive from Watertown Hotel and University Inn.
A Festive Stay at The Maxwell: Make your stay merry and bright with our Winter Wonderland Retreat or add a little holiday mischief with Grinch's Whoville Hideaway! Both upgrades come decked out with festive decor and holiday-inspired touches to make your getaway extra merry.
San Francisco: Ice Skating and Holiday Entertainment
Safeway Holiday Ice Rink: Enjoy outdoor skating and holiday festivities at Union Square's seasonal ice rink, open daily November 4, 2026–January 18, 2027 and less than a 10-minute walk from Staypineapple San Francisco.
San Francisco Symphony: Enjoy Dr. Seuss' How the Grinch Stole Christmas on the big screen with the score performed live by the Symphony on December 10–11, 2026, or catch Elf in Concert December 18–20, 2026. The Symphony is approximately a quick seven-minute drive from the hotel.
Winter Walk: Explore this festive holiday market along two blocks of Maiden Lane, featuring wooden chalets, local vendors, lush turf and Arctic-inspired decorations. Located right in the heart of Union Square and less than a 10-minute walk from Staypineapple San Francisco.
Portland: Festive Lights and Dazzling Displays
ZooLights: See the Oregon Zoo sparkle with millions of twinkling lights, glowing tunnels and life-size animal lanterns during ZooLights, November 20, 2026–January 3, 2027. The Oregon Zoo is approximately a quick 10-minute drive from Hotel Rose.
Winter Wonderland: Load up the car and cruise through more than two miles of dazzling holiday lights at Portland International Raceway, November 27–December 31, 2026. This festive drive-through experience is approximately a 12-minute drive from Hotel Rose.
Christmas Ships Parade: Watch a fleet of boats decked out in holiday lights sail along the Willamette and Columbia rivers, November 27–December 20, 2026. The parade passes several waterfront viewing spots, including areas just across the river from Hotel Rose, making it easy to catch the festive display nearby.
New York: Big City Holiday Traditions
Rockefeller Center: Don't miss the famous Christmas tree lighting on Wednesday, December 2, 2026. While you're there, enjoy a spin around the iconic ice-skating rink, open daily throughout the season. The festivities are just a short 15-minute subway ride from the hotel.
Radio City Rockettes: See the iconic Christmas Spectacular at Radio City Music Hall, November 4, 2026–January 4, 2027. This year's show features a brand-new contemporary tap number, "Ring." Radio City Music Hall is approximately a quick 17-minute subway ride from Staypineapple New York.
Grand Central Holiday Fair: Shop handcrafted jewelry, pottery, artwork and unique gifts from independent artisans at Vanderbilt Hall, November 9–December 24, 2026. Grand Central Terminal is approximately a quick 20-minute subway ride from Staypineapple New York.
Whether you're exploring a Christmas market, catching a holiday performance or enjoying a festive room upgrade, there's no shortage of ways to celebrate with Staypineapple. Pick your city, plan your festivities and we'll save you a spot under the double duvets!