Winter is nearly here, which means it’s the perfect time to start planning your holiday getaway to Chicago’s Northwest suburbs! This guide rounds up our top picks for holiday-themed pop-ups in the area. And with plenty of cozy accommodations nearby, we’ve also included some handy recommendations to help turn your holiday outing into a full weekend escape.
"Merry Christmas, ya filthy animal!"
Every year, Cortland’s Garage in Arlington Heights hosts its famous Home Alone pop-up, where the décor and drinks pay homage to everyone’s favorite holiday film. Did you know much of it was filmed nearby? This year, the pop-up is scheduled to run from November 12 through January 12.
For dinner, Cortland’s will serve up classic pub favorites and themed cocktails that even the “Wet Bandits” would approve of—perfect for anyone channeling their inner Kevin McCallister. Groups of eight or more should make a reservation, while all other seating is first-come, first-served.
Afterward, keep the night going with a stay at the DoubleTree by Hilton, conveniently located near downtown Arlington Heights, complete with an onsite restaurant and indoor pool.
November 12, 2025 - January 12, 2026
"Santa! Oh my god! I know him!"
In Itasca, the Westin Chicago Northwest will transform into an Elf-themed dining pop-up throughout December. The experience includes over-the-top North Pole decor and a special menu featuring seasonal dishes and playful cocktails inspired by Buddy the Elf himself! Pair the event with a stay at the Westin or nearby Country Inn & Suites to make a whole out of it!
Reservations for the Elf Pop-Up Holiday Experience are now open, so plan ahead and secure your seat!
December 1 - 29, 2025
"Scratchboard Chalet"
For a more adult-leaning experience, visit Arlington Heights’ Scratchboard Kitchen’s “Scratchboard Chalet” pop-up. According to the local guide, the 2025 event is set to run from November 28, 2025 through February 15, 2026. During this time, the space will take on the look of a cozy ski lodge. Think: ski-lift décor, warm wood tones, specialty dishes (French onion soup, grilled cheese sandwiches), and a mixology menu packed with seasonal flavors like peppermint and pumpkin spice!
Dress up or keep it cozy with your favorite winter layers—the décor leans chalet-chic either way. Arrive early to grab a table near the “ski-lift” photo wall. After dinner and drinks, unwind at a nearby boutique stay like the Chez Hotel, where you can stunning views of Chicago from the Chez Paul Rooftop Restaurant Bar.
November 28, 2025 - February 15, 2026
Experience the Holiday Season in Chicago Northwest
Don’t wait to start planning! These fun holiday pop-ups are time-limited and fill up quickly. Book your stay, reserve your table, and make any of these experiences the highlight of your holiday getaway in Chicago Northwest.
And if you’re looking for more seasonal events across the region, explore all sorts of other holiday happenings in the area, like photo ops with Santa, Christmas light displays, holiday markets, and more!
