FOR: Your free-spirited childhood friend, a natural healer and yogi
WHERE: Dana Hotel and Spa (660 N. State St.; 888-301-3262, danahotelandspa.com). From $250.
THE GIST: Bamboo floors and exposed cement ceilings give this 216-room boutique hotel the feel of an urban loft. A five-foot-long Vietnamese bell hanging in the lobby signals the worldly design touches throughout.
INSIDER TIP: Ask for a corner room. With two full walls of floor-to-ceiling windows, the spectacular views of State Street make a standard room seem positively deluxe.
SCENE AT THE BAR: In the ultraclubby Vertigo, on the roof of the 26th floor, party-happy 30-somethings chatter around the fire pit.
GOOD FOR: Your upper-crust mother-in-law, decked out in pearls and couture
WHERE: Elysian (11 E. Walton St.; 312-646-1300, elysianhotels.com). From $385.
THE GIST: With only ten rooms per floor, this hotel feels more like a high-end condominium. The fireplaces and in-mirror TVs in almost every room and 1920s–Paris–inspired décor only add to the niceties.
INSIDER TIP: A complimentary courtesy car takes guests anywhere within a two-mile radius.
SCENE AT THE BAR: With its deep leather chairs, Bernard’s Bar could be an exclusive gentlemen’s clubhouse, but drinks like the Aviation—with gin and crème de violette ($14)—are female friendly.
GOOD FOR: Your workaholic uncle, who’s in town for a conference. Period.
WHERE: JW Marriott (151 W. Adams St.; 312-660-8200, jwmarriottchicago.com). From $219.
THE GIST: Housed in a classic Daniel Burnham building in the Loop, this 610-room hotel offers ample meeting space and an Italian bistro helmed by the hotshot chef Todd Stein.
INSIDER TIP: Valeo, the 20,000-square-foot spa and fitness center, offers an exclusive wellness class with Shea Vaughn (mother of Vince).
SCENE AT THE BAR: The standard beer list and generous supply of TVs attract an afterwork, sports-loving crew.
GOOD FOR: Your sister, her husband, and their five little ones
WHERE: Avenue Crowne Plaza (160 E. Huron St.; 312-787-2900, http://avenuehotelchicago.com). From $99.
THE GIST: With pintsize bathrobes, Fatboy beanbag chairs, multicolor bedding, and Wii games in some quarters, this recently renovated 351-room hotel has the most kid appeal of the bunch.
INSIDER TIP: A 40th-floor outdoor pool offers spectacular views of the city.
SCENE AT THE BAR: Connected to the lobby, the English-style pub Elephant & Castle caters to the happy-hour crowd and tourists.
GOOD FOR: Your husband’s frat buddies, in town for a bachelor part
WHERE: Trump International Hotel & Tower (401 N. Wabash Ave.; 312-588-8000, trumpchicagohotel.com). From $525.
THE GIST: The Italian marble columns, walls paneled with zebrawood, and Swarovski-encrusted water bottles are over-the-top Trump.
INSIDER TIP: For groups, book a suite (from $945)—the fireplace and larger-than-life kitchen alone are worth it.
SCENE AT THE BAR: The mezzanine-level lounge, Rebar, is filled with gussied-up young locals quaffing punch-bowl-size concoctions such as white sangria and elderflower.
GOOD FOR: Your foodie best friend, chasing lunch trucks and tickets to Next
WHERE: Affinia (166 E. Superior St.; 312-787-6000, affinia.com). From $159.
THE GIST: The bi-level entryway gives these bright rooms an apartment-like touch, and the experience is totally customizable, including choice of pillow (from Swedish memory foam to ones with MP3 plug-ins).
INSIDER TIP: A three-course lunch at White House guest chef Marcus Samuelsson’s C-House restaurant costs a mere $15.
SCENE AT THE BAR: Relax with a low-key mix of older diners and couples at the never-too-crowded C-Bar. Or head up to the 29th floor’s charming rooftop bar, C-View.
GOOD FOR: Your concert-loving hipster brother, who thinks downtown is for losers, man
WHERE: The Inn at Longman & Eagle (2657 N. Kedzie Ave.; 773-276-7110, longmanandeagle.com). From $75.
THE GIST: Furnished with custom-made reclaimed-wood furniture, local art, and Apple TVs, this inn feels minimalistic in an urban-chic kind of way.
INSIDER TIP: Book a room and you’re guaranteed a spot in the no-reservations, always-packed restaurant downstairs. Or order in.
SCENE AT THE BAR: A sea of skinny jeans, plus old-school foodies, crams by the bar, waiting for a table. Inn guests exchange complimentary tokens for shots from the 30-strong whiskey list.