Best One-Night-Only Couture
Fashion blogger Janet Mandell got her start by opening her closet to loan out her one-of-a-kind designer clothes. Now, with By:Fashionaholic, when a big night beckons, her stylists can outfit you from head to toe with an extensive showroom of knockout looks. Full looks from $500, 311 W. Superior St.
Best Trainer for Urban Pups
The dedicated team of dog lovers at Found Chicago Boarding & Training Center will get your pup house-trained, socialized and exercised—everything needed to make a city dog one of the pack. 4108 N. Rockwell St.
Best Place to Board a Champion
Caitlyn Shiels provides boarding and training at her new True North Stables. The barn excels at taking both horse and rider to the next level. 41900 N. Delany Road, Zion
Best Art Tours for Collectors
Led by Cynthia Noble, who is an adjunct lecturer at the Art Institute of Chicago, Noble Art Tours offer an insider’s view of the art world with private tours of museums, galleries and art spaces in Chicago. Tours from $250 per hour, with extra charges for pre-opening-hours access
Best Place to Launch Your New Venture
With incubation services, mentors and licensed kitchens, The Hatchery Chicago is the place to take your much-dreamed-about idea and turn it into a reality. 135 N. Kedzie Ave.
Best Way to Give Yourself Space
Doorage is a new Chicago-based service that will send packers and a custom storage container to you. Once they pack all your excess treasures, the team takes the container to a secure storage facility and out of your way. Half-day packing from $540, storage fees based on volume
Best Way to Float Above it All
Chicagoland’s only pilot-owned ballooning company, Nostalgia Ballooning takes you into the clouds on a private ride for up to six people. To complete the experience, a Champagne toast is provided upon landing. Rides from $500 per person
Best Hotel to Find the Next Kerry James Marshall
Newly upgraded, The Blackstone offers spacious rooms and incredible views, but if you’re interested in art, be sure to check out the more than 1,600 pieces, including from the art hall on the fifth floor, which displays works by mostly Chicago artists. Suites from $300, 636 S. Michigan Ave.
Best Hotel For a Couples Winter Staycation
The Gold Coast Grandeur is an exclusive package at the Four Seasons Hotel Chicago that starts with the spectacular Lakeview Executive Suite; includes a mobile mixologist starting your evening off in style; and ends with an 80-minute couples massage, private use of the 50-foot pool, Champagne, and lots and lots of romance. Package from $1,335 per night, 120 E. Delaware Place
Best Secret Wine Club We Can Still Tell You About
Revel in the top-secret vibes at Birch Road Cellar, accessible to members via a fingerprint-coded door for carefree socializing. The members-only BYOB social club touts private lockers for your stash of wine and spirits, and exclusive events and tastings. Memberships from $89 per month
Best Way To Learn From The Pros
Iliana Regan isn’t the first chef to turn food into an art form, but she might be one of the first to let us all in on the secret. The Elizabeth and Kitsune chef offers eight-week cooking classes that teach everything from pasta to pan sauces, teaming up with wife and sommelier Anna Regan for the latter’s wine expertise. 4835 N. Western Ave., $1,000
Best Place to Play with a Broom
Who says the sport of curling isn’t glam? Not anyone who has been to The Gwen Chicago’s new curling cabin and rink. On the fifth-floor terrace is a cozy just-for-winter venue with a special food-and-drinks menu. 521 N. Rush St.