Eat
The old: Gene & Georgetti
If it gets any more old-school than this circa 1941 steakhouse, we haven’t seen it. Filling every inch of the wood-lined dining room are vinyl bar stools, chairs and banquettes as blood-red as the steaks (both well-aged, we might add). Servers range from formal to gruff, but they mean well and deliver the goods: textbook veal vesuvio, a ‘garbage salad’ (with a little bit of everything) fit for four, calf’s liver sautéed with onions and bacon, perfectly seared chops, and garlicky shrimp de Jonghe casserole that the veteran staff swear the joint invented. Believe ’em – these are the Chicago old-boys you don’t want to piss off. 500 N Franklin St, +1 312 527 3718; www.geneandgeorgetti.com.

The new: Custom House
The meat-centric arm of the Spring/Green Zebra family is considered a steakhouse by some, but don’t expect Sinatra, Gibson martinis and teamsters wolfing down porterhouses. Instead, perfectly executed Berkshire pork chops, roasted New York strips and braised bone-in shortribs are served with sides that up both the ante and the seasonal factor. Fresh-faced servers might not know your name, but they know the name of every farmer who had a hand in what’s on the plate, and for some diners, that's just as important. 500 S Dearborn St, +1 312 523 0200; www.customhouse.cc.

Sleep
The old: The Drake
The Drake epitomises old-world glamour in every sense of the word. Meeting rooms and lobbies are still adorned with Oriental rugs and chandeliers, high tea is served daily in the Palm Court and lavish weddings for the rich and famous are held in stadium-sized banquet rooms. But all is not frozen in time: rooms have been updated with amenities like high-speed internet access and non-allergenic pillows to ensure twenty-first-century comfort and style. 140 East Walton Place, +1 312 787 2200; www.thedrakehotel.com.

The new: Hotel Felix
The lovely Hotel Felix beats out other Chicago hostelries (even trumping nearby Trump’s) by having the distinction of having the city’s first silver LEED certificate for environmental sustainability. This eco-chic newcomer is located in a charming brick building dating back to the 1920s and while its lobby is rather intimate (ie cramped), each of the 224 guest rooms are bathed in gentle, earthy colours and fitted with amenities like high-speed internet access and flat-screen TVs. 111 W Huron St, +1 312 447 3440; www.hotelfelixchicago.com.

Do
The old: Blue Man Group
What happened to those high-school guys who always drummed on things and grossed you out by cramming weird stuff in their mouths? They graduated to Blue Man Group, where city-park miming goes techno. Three indigo dudes offer kiddie fun for grown-ups in this kinetic show that’s a classic go-to option for out-of-towners looking for a show. Briar Street Theatre, 3133 N Halsted St, +1 773 348 4000; www.blueman.com.

The new: Too Much Light Makes the Baby Go Blind
This wonderful, preposterously named show actually predates Blue Man Group’s appearance in Chicago – it’s the city’s longest-running play, in its twentieth year. However, it’s generally considered too loopy to be recommended in your run-of-the-mill guidebook. TMLMTBGB features an ensemble of writer-performers attempting to perform 30 mini-plays in 60 minutes. The resulting hour is equal parts block party and populist performance art: high in creativity, broad in appeal and affordable in price. At the Neo-Futurarium, 5153 N Ashland Ave, +1 773 275 5255; www.neofuturists.org.

For more information, see Time Out Chicago.

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