Before making your list and checking it twice, explore these 10 luxe gifts and experiences in Chicago that are sure to impress everyone on your list this holiday season.
The Night Spa at Four Seasons Hotel Chicago
What’s more romantic than a couple’s spa experience at the Four Seasons? Having the entire completely renovated spa to yourself after hours. From 8:30-11 p.m., you’ll enjoy a couple’s massage on the pool deck with Champagne plus treats from the hotel’s pastry team, followed by private infinity pool and heated whirlpool access, all with stunning city views. From $2,300
Wine Tasting at The Cellar Door
Tucked away off the main dining room of new Fulton Market hot spot The Oakville Grill & Cellar, this cozy enclave gives wine country vibes and makes an ideal spot for a tasting experience featuring vintages from top California wineries (including featured December winery Villa Creek). With room for just six, it’s a memorable gift for the oenophiles in your life. $80 per person (chef-curated charcuterie supplement $48)
The Signature Wine Experience at AIRE Ancient Baths Chicago
There’s no more romantic spa setting in Chicago than AIRE, a dimly lit destination featuring a series of hot and cold baths set in a restored factory complete with original exposed brick, wooden beams and industrial columns. AIRE’s most unique offering? The Signature Wine Experience, where you and your partner can submerge yourself completely in antioxidant-rich wine made from Spanish Ribera del Duero red grapes while receiving a cranial massage and, afterward, an hour-long massage with grapeseed oil. $1200
Live Like a Legend Package at InterContinental Chicago Magnificent Mile
Finish up ’23 in style like #23 with this Mag Mile hotel’s Michael Jordan-themed package, which includes accommodations in the palatial Presidential Suite; dinner for two at Michael Jordan’s Steak House; the chance to see a Chicago Bulls game courtside or host a private pool party for five friends; custom Air Jordans; and even time to shoot some hoops. From $32,000
Private Tasting at Milk Room
Step inside this dark, tucked-away eight-seat spot at the Chicago Athletic Association hotel, and it’s not hard to imagine the room’s days as a members-only speakeasy during Prohibition. Stocked with vintage spirits and curated whiskies, it’s an atmosphere-packed destination for thoughtful imbibing—and an ideal spot for an exclusive tasting for you and nine of your nearest and dearest. $2,000
Private Skating Party at The Peninsula Sky Rink
Forget the lines at the city’s public skating rinks and book the Peninsula Chicago’s 4th-floor terrace rink for an afternoon or evening with friends, family, or even to propose to that special someone. Skates are included in the fee (with a donation for each skate rental made to two children’s charities), and the rink can accommodate roughly 15 skaters at a time. December rates from $10,000; Jan./Feb. rates from $5,000 (food and beverage minimums apply).
Whole Animal Experience at Frontier
For the carnivore in your life, this meaty gift just might be the ultimate gesture of affection. Choose your animal, from wild boar, goat and alligator to lamb, pig and more, and Frontier executive chef/owner and 2022 Chopped champion Brian Jupiter and team will present and serve the entire beast to your group along with delectable sides like 5-cheese mac, Caesar salad, seasonal vegetables and buttered rolls. $400-$875
Private Getaway at Bunker Hill Farms
Nestled just an hour northwest of Chicago on 450 private acres, this luxe getaway can become your group’s private playground for a one-day and night adventure. Indulge in an all-inclusive experience with personalized activities, including ATV adventures, shooting activities, golf and more, plus gourmet meals, relaxation time in the tree-top Silo Spa, and other outdoor adventures. With a private lake, entertainment room, and even winter activities, this A-list favorite offers an unmatched retreat for those seeking opulent seclusion. From $10,000
De Punta a Punta Experience at Jaleo Chicago
A tasting menu experience so unique it’s only offered the first Thursday of each month, this evening at José Andrés’ River North tapas destination kicks off three waves of tapas in the Jaleo dining room followed by three cocktails and more bites in the Pigtail speakeasy, ending with dessert. $180 per person (advance reservations required)
Private Cooking Classes at Tutore Cooking School
Ever dreamt of cooking Italian food like a master chef? Whether you’re a novice in the kitchen or just wanting to polish your pasta-making skills, you and yours (up to 30 people total) can enjoy a private class from two of Chicago’s most experienced Italian chefs at this recently opened cooking school on the northwest side. December highlights include a class on timpano making—aka that ginormous pasta creation from Big Night—as well as a holiday baking class on Italian Christmas cookies and a truffle-centric Piedmontese night. December rates from $2,500; January rates from $2,000
Photography by: Cellar Door photo by Lindsay Eberly; Bunker Hill Farms photo by Kellie Bucci; other photos courtesy of brands
