Mad Men fans will appreciate the exquisite balance of throwback vibe and new decor at this no-expense-spared River North steak house near Trump Tower.

The a la carte menu isn't cheap, but the big slabs of beef are succulent; the cocktails are heavy on the liquor; and the sharp, creamy mac and cheese side is worth the indulgence. Regulars who love their wine can store favorites by the bottle near the reception desk, in a locked case marked by a brass plaque with their name. Paging Don Draper! (312) 626-2444; bennyschophouse.com [2]

Benny's Chop House [3]

"Cheese, swine and wine" rule along North Michigan Avenue. Choose your adventure when you sit at one of the communal tables in the dining room. Think you're up for pig's tails braised in balsamic dressing? A good amount of fat marbles the chunks of meat, helping them melt in your mouth. Sliced super thin, the pig's ear comes served with crispy kale, pickled cherry peppers and fried egg.

If some of the unusual offerings aren't your bag, that's OK, says Chef Jimmy Bannos Jr. (pictured at left). Try the milk-braised pork shoulder, a large cut of tender meat on top of mashed potatoes. Just don't be surprised if the stranger sitting next to you in this lively spot asks for some -- or offers to share theirs. (312) 464-1744; thepurplepigchicago.com [12]

The Purple Pig [13]

Glossy hardwood floors, high tin ceilings and walls of red glass greet patrons at this River North eatery. Unlike most casual Mexican restaurants, Dos Diablos doesn't try to offer dozens of meals. It does a handful of entrees and does them well, including the Baja fish tacos, warm tortillas filled with grilled tilapia and topped with lime-cilantro crema. The margaritas and tortilla chips alone are worth the trip. (312) 245-3100; dosdiabloschicago.com [22]

Dos Diablos [23]

The clenched-fist taps at this brewpub off the Kennedy Expressway shout a "power to the people" message that resonates in this gritty Logan Square neighborhood.

The menu here seems decidedly creative -- standard appetizers, sandwiches and pizzas elevated with a few key ingredients (two examples: a honey-jalapeno slaw on a smoked pulled pork sandwich and the cremini mushrooms and shallots in the burgers). Don't go home without trying Bottom Up Belgian Wit, a smooth ale with a touch of orange, best downed with bacon-fat popcorn. (773) 227-2739; revbrew.com [30]

Revolution Brewing [31]

The food-truck craze has landed in the Heartland, and these "naan-wiches" are street food for foodies. Try the warm lobster club with pancetta-tomato-onion salad and arugula pesto; duck confit with melted leeks, Brie and apple chutney; or the butternut squash with mascarpone, sage, hazelnuts and poached onions. But first, you'll have to find this roving kitchen lab, so go online. The website posts the week's schedule on cute sticky notes. (773) 942-6152; gaztro-wagon.com [40]

Gaztro-Wagon [41]

This suburb along the Burlington Northern train line (16 miles west of the Loop) has blossomed into a surprise destination for inventive dining. New additions include:

Prasino This organic, green cafe offers breakfast, lunch and dinner, with as much attention paid to the Niman Ranch beef short rib as to the lobster-stuffed avocado topped with mango salsa. And despite the upscale atmosphere, kids are as welcome as food critics. (708) 469-7058; prasino.com [50]

Di Nico's Pizza The aroma wafting out of the front doors of this tiny storefront reminds us of New York pizza parlors. But these slices are even bigger, about a quarter of a medium pie. After you've tried the vegetable panini and the house-made seasonal gelato, you'll be a fan of these fresh, cheap eats. (708) 352-9800; dinicospizza.com [51]

Prasino [52]

Di Nico's Pizza [53]