You can’t get away, but you don’t have central air conditioning. Or a pool. Or a private beach, or a hot tub, or a cook. And you definitely don’t have a masseuse. But they do. —Heather Kenny
Hotel Burnham Half the space in this former office building, designed by Daniel Burnham and built in 1894, features original wood-and-glass doors, iron grillwork, and marble stairs. When he wasn’t feeling up to snuff, Al Capone visited his doctor in what’s now room 809. Special deals on offer include credit toward a meal at the hotel’s restaurant, Atwood Cafe; the “First Love” package gets you that as well as champagne, chocolate, and late checkout. 
1 W. Washington, 312-782-1111, burnhamhotel.com, $209-$549 per night.
The Drake For years, the Drake was the ne plus ultra of Chicago hotel experiences. Its gloried past can be evoked by taking tea in the Palm Court, bellying up to the bar in the Cape Cod Room (where Marilyn Monroe and Joe DiMaggio’s carved initials can still be seen), or having a martini in the dim, old-fashioned atmosphere of the Coq d’Or, which was issued one of the first city liquor licenses at the end of Prohibition. Perks like a $75 Bloomingdale’s gift card accompany a shop-till-you-drop package deal, and a romantic getaway offer comes with champagne and late checkout. 140 E. Walton, 312-787-2200, thedrakehotel.com, $249-$2,500 per night.
InterContinental This hotel is made up of two buildings, one of which was built in 1929 as the home of the lavishly decorated Medinah Athletic Club. Some of those original design elements are best experienced in the junior-Olympic-size pool, located in an oasislike space featuring majolica tiles, Roman arches, and a terra-cotta fountain of Neptune. An “Economic Stimulus” deal starts at $209 a night and includes a $50 dining credit and half off valet parking. 505 N. Michigan, 312-321-8766, icchicagohotel.com, $279-$359 per night.
Peninsula If you’ve got the cheese, the Peninsula is the place to go for the ultimate pampering. Known for its melding of Eastern and Western elements in everything from decor to dining, the hotel offers two well-regarded restaurants (Avenues and the Shanghai Terrace), a spa that’s regularly rated one of the best in the country, and an indoor pool with a spectacular view through 20-foot windows. Private cooking lessons and Chinese tea ceremony demonstrations are available, and a chocolate buffet every Friday and Saturday evening is the cherry on top. A “Summer Splendor” package, available until 9/6, offers rooms starting at $450 and a choice between a picnic (with wine and snacks) in Millennium Park or a visit for two to the Art Institute. 108 E. Superior, 312-337-2888, peninsula.com, $575-$8,000 per night.
Ravinia Guest House After their kids grew up, the couple that owns this 1926 home in the posh, wooded North Shore suburb of Highland Park decided to open a B and B. It’s popular with attendees of the nearby Ravinia Music Festival; guests also have access to a private neighborhood beach about a block and half away. Breakfast features homemade muffins, breads, and hot dishes like apple pancakes. 264 Oakland, Highland Park, 847-433-3140, bbonline.com/il/ravinia/index.html, $149.50 per night.
Ruby Room More like a spa with a hotel than a hotel with a spa, Ruby Room offers sleek guest rooms and services ranging from the standard massages and makeup lessons to chakra energy healing, auratherapy, and an herbal treatment called moxabustion. Special package deals include restaurant gift certificates, complimentary champagne and chocolates, or a free night. 1743-45 W. Division, 773-235-2323, rubyroom.com, $155-$185 per night.
Villa D’ Citta This historic landmark building dating from 1887 offers the chance to live like a well-heeled Lincoln Parker for a couple of days. The interior combines classic decor such as four-poster beds and arched windows with contemporary design. There’s a sundeck with a hot tub and a sunken, brick-lined “grotto” for hanging out. 2230 N. Halsted, 800-228-6070, villadcitta.com, $129-$399 per night.
Wheeler Mansion This landmark home in the historic Prairie Avenue District is one of the few remaining mansions that predate the Great Chicago Fire. Decor like antique furniture, hand-painted bath tiles, and printed wallpaper harks back to that age; the house also features elegant gardens. 2020 S. Calumet, 312-945-2020, $235-$365 per night.