Its loan portfolio includes, among other things, investments in high-end kitchenware maker Sur La Table, a crane rental company, restaurant groups and software makers.

FORBES: Private Equity For Coupon Clippers

McDonald's also began using new software recently that helps restaurant owners decide the optimal number of employees to have on hand at a given time.

WSJ: McDonald's Tackles Repair of 'Broken' Service

Larger bets run the gamut of industries, including print media, online education, hand tools, restaurant chains and, of course, software.

FORBES: Patient Capital

When the software program is used to locate a nearby restaurant or store, a small ad appears at the bottom of the screen for another establishment.

CNN: GPS to do wonders for wireless browsing

The founder of the company, Mounir Shita, envisions a network of connected devices that use so-called smart software agents to track your friends, suggest food at a restaurant and even find someone to paint your house.

ENGADGET: Kimera Systems wants your smartphone to think for you Alt

Other Windy City players that have made headlines in recent months include (though not in as infamous a fashion as Groupon) mobile marketing firm Vibe Media, food delivery and restaurant finder company GrubHub, online trading platform optionMONSTER (home of tradeMONSTER) and personnel management software company SilkRoad.

FORBES: Tech Startup City: G2 Crowd in Chicago