This holiday season, unless you’re eager to cede control of your couch and your TV remote, you’re going to need a compulsively researched no-fail list of Chicago hotels where you can confidently park all of your visitors. We canvassed the city for suggestions, ranging from art-school-cool boutiques that will charm your friends without breaking the bank to sure-fire splurges guaranteed to please even your discerning mother-in-law. And in case it’s you and your sweetie who need to escape it all, our list includes picks for three of the city’s most romantic hotels. ’Tis the season, after all, for snuggling up and rekindling the flame. See below to start booking.
FOR: Your discerning mother-in-law
WHERE: Peninsula (108 E. Superior St., 312-337-2888, peninsula.com/chicago) From $395.
THE GIST: Surrounded by elegance and Far Eastern hospitality, high-maintenance relatives will breathe their first sighs of relief when they spy, on the fifth floor, the palatial restaurant with its gold-domed ceiling. (The Sunday brunch is $75—and extraordinary.) But they can truly exhale in the big classic guest rooms, which offer Michigan Avenue views and bathtubs with TVs. Kids who score a night with their grandparents will love the Pen Kids’ Academy, which organizes scavenger hunts ($49). Grandma, meanwhile, can de-stress in the dreamy spa with an aromatherapy massage ($165)
KEY TO SYMBOLS
Good value 
Boutique (<200 rooms) 
Family friendly 
Great bar scene 
Trendy restaurant
Scenery (views, etc.) 
Pool 
Spa 
Free Wi-Fi 
24-hour room service
RELATED: The Extras: best lobby art, best bath products, most stylish lounge, and more »
Photograph: Nathan Kirkman
FOR: Your Tony aunt and uncle
WHERE: Four Seasons (120 E. Delaware Pl., 312-280-8800, fourseasons.com/chicagofs) From $399.
THE GIST: Their requirement: a hotel near Michigan Avenue and Oak Street that boasts unparalleled lake views. Your answer: one of the 435 rooms of this refined hotel atop the 900 North Michigan Shops. The Four Seasons conveys luxury with its tall windows, marble bathrooms stocked with L’Occitane products, and the museum-quality art in its meandering public spaces. But guests will also discover refreshing doses of whimsy throughout, such as the optic prints in the lobby by Julian Opie and an incredible homemade hot dog ($14) in the comfort-food-driven restaurant, Allium.
KEY TO SYMBOLS
Good value Boutique (<200 rooms) Family friendly Great bar scene Trendy restaurant
Scenery (views, etc.) Pool Spa Free Wi-Fi 24-hour room service
RELATED: The Extras: best lobby art, best bath products, most stylish lounge, and more »
Photograph: Peter Vitale
FOR: Relatives on a budget
WHERE: Hotel Lincoln (1816 N. Clark St., 312-254-4700, hotellincolnchicago.com) From $139.
THE GIST: It’s been nine months since this kitschy-cool, family-friendly hotel with something for everyone opened across the street from Lincoln Park. Locavores have fallen hard for its farm-to-table restaurant, Perennial Virant, while history buffs tout the local curiosities and art riffing on Chicago’s past. (Case in point: The J. Parker, the hotel’s rooftop lounge, is named for the officer who vacated his post outside Abraham Lincoln’s theatre box for the tavern the night the president was assassinated.) Kids will love the proximity to Lincoln Park Zoo, as well as J. Parker’s fresh fruit mocktails. Three colorful family suites (from $189) are equipped with bunk beds and extras like Lincoln Logs and an Xbox. Complimentary bicycles come with safari-style helmets.
KEY TO SYMBOLS
Good value Boutique (<200 rooms) Family friendly Great bar scene Trendy restaurant
Scenery (views, etc.) Pool Spa Free Wi-Fi 24-hour room service
RELATED: The Extras: best lobby art, best bath products, most stylish lounge, and more »
Photograph: Paul Dyer
FOR: Your friends the architecture buffs
WHERE: Radisson Blu Aqua (221 N. Columbus Dr., 312-565-5258, radissonblu.com/aquahotel-chicago) From $149.
THE GIST: Minneapolis-based Radisson chose wisely last November when it picked Aqua, the Jeanne Gang–designed marvel overlooking Millennium Park, for the North American debut of its upscale brand Blu. Rather than gawk at the curvaceous landmark from the sidewalk, architecture aficionados can canvass the skyline from a balcony—no two are the same—off one of Blu’s 334 rooms. The mantra for the interiors is tranquility: sleek metal design elements, warm lighting, and wood floors. Likewise, the 80,000-square-foot outdoor green deck on the third floor is outfitted with a sizable pool, walking trail, and Zen garden.
KEY TO SYMBOLS
Good value Boutique (<200 rooms) Family friendly Great bar scene Trendy restaurant
Scenery (views, etc.) Pool Spa Free Wi-Fi 24-hour room service
RELATED: The Extras: best lobby art, best bath products, most stylish lounge, and more »
Photograph: Courtesy of hotel
FOR: Your sister and her rambunctious family
WHERE: Swissôtel (323 E. Wacker Dr., 312-565-0565, swissotelchicago.com) From $179.
THE GIST: You’ve seen this towering triangle in the skyline countless times. Here’s a news flash for parents (or grandparents): The classy Harry Weese–designed Swissôtel, which underwent an extensive renovation in April, offers great programming for the under-12 set. Kids can swim in the 42nd-floor indoor pool, wolf down an excellent hot breakfast in the restaurant Geneva, and stomp around the playground and park behind the hotel. And while the family suite package may sound steep at $529 a night, consider that it includes a common living space, a separate room for parents, and a colorful kids’ room stocked with toys and games. It also includes four passes to the museum of your choice (a $100 value).
KEY TO SYMBOLS
Good value Boutique (<200 rooms) Family friendly Great bar scene Trendy restaurant
Scenery (views, etc.) Pool Spa Free Wi-Fi 24-hour room service
RELATED: The Extras: best lobby art, best bath products, most stylish lounge, and more »
Photograph: Courtesy of hotel
FOR: Your arty college roommate and her boyfriend
WHERE: Acme Hotel Company (15 E. Ohio St., 312-894-0800, acmehotelcompany.com) From $169; suites from $259.
THE GIST: Pop art meets high-tech design at this 15-floor, 130-room River North boutique hotel with lava lamps in the lobby and album covers from the likes of MGMT in the elevators. The hipster design details catch the eye, but the tech flourishes really elevate this under-the-radar spot. Rooms are equipped with LED lamps and free 100 MB bandwidth Wi-Fi for fast browsing, and suites feature B&W Zeppelin audio systems. There’s no lobby bar or restaurant yet; both are expected by the end of the year. But a thermos of hot coffee will appear outside guests’ doors at any time they request.
KEY TO SYMBOLS
Good value Boutique (<200 rooms) Family friendly Great bar scene Trendy restaurant
Scenery (views, etc.) Pool Spa Free Wi-Fi 24-hour room service
RELATED: The Extras: best lobby art, best bath products, most stylish lounge, and more »
Photograph: Courtesy of hotel
FOR: Shopaholics
WHERE: Park Hyatt (800 N. Michigan Ave., 312-335-1234, parkchicago.hyatt.com) From $395.
THE GIST: Forget the chain-hotel ambiance that the word “Hyatt” conjures up. The brand’s flagship makes magic by compressing the best amenities—service, art, cuisine, and posh room details—into a beautiful hotel that shines in the middle of Michigan Avenue mayhem. The pièce de résistance is the newly refreshed seventh floor, where guests can linger over dinner at NoMI Kitchen or sip cocktails on the rooftop terrace. If the sky’s the limit, book the 1,400-square-foot Bottega Veneta suite (from $4,500), which overlooks the lake and is outfitted with furnishings from the fashion house.
KEY TO SYMBOLS
Good value Boutique (<200 rooms) Family friendly Great bar scene Trendy restaurant
Scenery (views, etc.) Pool Spa Free Wi-Fi 24-hour room service
RELATED: The Extras: best lobby art, best bath products, most stylish lounge, and more »
Photograph: Courtesy of hotel
FOR: You and your sweetie
WHERE: Trump International Hotel & Tower (401 N. Wabash Ave., 312-588-8000, trumpchicagohotel.com) From $395.
THE GIST: There’s no better place to hole up for 24 hours (or more) and be spoiled than here at one of the city’s most intensely service-driven hotels. The rooms are well appointed, with ten-foot floor–to-ceiling windows, in-mirror TVs, and kitchens equipped with Sub-Zero mini fridges. In September, the celebrity hairstylist Anthony Cristiano unveiled his new salon, which houses an exclusive Caron Paris perfume boutique.
KEY TO SYMBOLS
Good value Boutique (<200 rooms) Family friendly Great bar scene Trendy restaurant
Scenery (views, etc.) Pool Spa Free Wi-Fi 24-hour room service
RELATED: The Extras: best lobby art, best bath products, most stylish lounge, and more »
Photograph: Courtesy of hotel
FOR: You and your sweetie
WHERE: Public (1301 N. State Pkwy., 312-787-3700, publichotels.com) From $195.
THE GIST: Ian Schrager’s first foray into the Chicago market reflects his “less isn’t just more, it’s better” philosophy with its airy 16-foot lobby ceilings, minimalist palette, and location on a subdued stretch of the Gold Coast. The hotel’s proximity to the lake and to Rush Street makes it a good choice for couples who want a night on the town. For those who prefer to stay in, a gilded lounge and the refurbished Pump Room pulse with the energy of a see-and-be-seen crowd.
KEY TO SYMBOLS
Good value Boutique (<200 rooms) Family friendly Great bar scene Trendy restaurant
Scenery (views, etc.) Pool Spa Free Wi-Fi 24-hour room service
RELATED: The Extras: best lobby art, best bath products, most stylish lounge, and more »
Photograph: Courtesy of hotel
FOR: You and your sweetie
WHERE: Waldorf Astoria (11 E. Walton St., 312-646-1300, waldorfastoria.hilton.com/chicago) From $395.
THE GIST: Couples will be hard-pressed to find anything more romantic than the former Elysian, which was absorbed into the Waldorf empire in February. Opulent in its Coco Chanel–inspired design, the 188-room hotel in prime Oak Street territory conveys refinement from the start with its heated cobblestone driveway and no-tipping policy. Secluded in feeling but not remote, the hotel fosters togetherness with its residential-style rooms, fireplaces, private balconies with views, and couples’ massages ($320). Though it currently lacks a fine-dining spot (at presstime, there was no reopening date set for Ria), the hotel’s bistro-style Balsan is no slouch, serving fresh seafood platters with oysters and lobster (from $70) and its regionally themed Sunday Suppers ($31). Guests who would rather snuggle in their room can opt for custom plates and cocktails delivered by room service.
KEY TO SYMBOLS
Good value Boutique (<200 rooms) Family friendly Great bar scene Trendy restaurant
Scenery (views, etc.) Pool Spa Free Wi-Fi 24-hour room service
RELATED: The Extras: best lobby art, best bath products, most stylish lounge, and more »
Photograph: Courtesy of Waldorf Astoria Hotels & Resorts