The city's broad shoulders aren't nearly as important as its broad sidewalks and bus and subway options when it comes to walkability.
The city's restaurants, theaters, shops and other amenities are closer and more accessible the nearer one gets to Lake Michigan. Lake View and Wrigleyville or West Town and Wicker Park are great place for living car free. Stray too far west or south, however, and you'll end up in the 4% of Chicago neighborhoods that need an automotive assist.
The Chicago Transit Authority helps level the extremely wide playing field with buses and trains that helped roughly 515 million riders get through the city last year. That includes the throngs of tourists and business travelers flying into O'Hare and Midway and taking CTA trains into the city. Another 70.5 million riders who take the commuter rail in from the suburbs each day make a strong argument to keep the car under wraps until the snow stops falling.
The town can still be a mixed bag when it comes to getting around, however. If you're barhopping or looking for good Italian beef in Old Town, Lincoln Park or Near North Side, you won't have to stray far. If you're trying to make it to a play in Pilsen after a barbecue in New City, however, it's a crapshoot.