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 
Yes, cupcakes are everywhere, and yes, selling them ice-cream-truck-style feels a little gimmicky. But these cupcakes are amazingly moist. And they're so different from one another.
Take the McDreamy -- chocolate with chocolate and cream cheese frosting and filling. Or the Curious George, a chocolate-banana treat with salted caramel Italian buttercream frosting. Or the red velvet, topped with thick cream cheesy frosting. Tracking them down is easy -- just check out the website and then look for the line of people near the light blue van. (312) 852-4441; flirtycupcakes.com 
Flirty Cupcakes 
"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 
The Purple Pig 
Most of us don't think of fine cuisine when we dine sans silverware. But that happens every night in Rogers Park. Patrons pick up their stews, meats and veggies with pieces of injera bread, a spongy African version of Middle Eastern pita.
Start with sambusa, light crispy bread shells stuffed with minced meat, before moving on to kay watt, lean beef cubes dressed in a spicy sauce, and the chocolate diamond, a welcome take on gooey lava cake. (773) 764-2200; ethiopiandiamondcuisine.com 
Ethiopian Diamond II 
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 
Dos Diablos 
You wouldn't plan a special trip just to hit this Wicker Park breakfast and lunch spot, but we love the way the food reflects the neighborhood's artsy reputation. So if you're nearby, stop in for a fresh-made bagel with a schmear of olive relish, white truffle and toasted pine nuts, or a lox sandwich heaped with salmon, tomato, red onion, cucumber, capers and cream cheese. (773) 772-2243
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 
Revolution Brewing 
What do you get when you cross a fine-dining chef with a gourmet hot dog concept? Sausages made from fresh pork, beef and lamb and topped with ingredients you'd expect to see at Trump's Sixteen and the sleek, chic Blackbird (where the chef once worked).
The Brunch Dog, a pork loin sausage dressed with Cobb-smoked bacon, fried egg and maple mayo will make you wonder how you'll ever eat grocery-aisle dogs again, and it'll definitely bring you back to this North and Clybourn neighborhood spot. (312) 281-5187; franksndawgs.com 
Franks 'n' Dawgs 
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 
We know you've heard of wine flights. But bacon flights rule in this upscale Lakeview diner. Think maple-pepper bacon, jalapeno bacon, honey bacon, mesquite and cherry-smoked bacon, plus a bacon waffle and a caramelized onion and bacon frittata.
If bacon isn't your thing, consider the cinnamon-raisin sandwich made with eggs, chicken-apple sausage, aged cheddar and maple syrup. Get a cup of Chicago's Intelligentsia coffee alongside, and you won't mind that you have to wait a little longer than usual for your food. (773) 525-7005; bakinandeggschicago.com 
Bakin' and Eggs 
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 
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 
Di Nico's Pizza