Inter, who went into the game without a win in their four previous Serie A outings, had the better of the early exchanges but were left reeling after a quick-fire double from Di Vaio shortly before the break.
Inter tried to rally in the second period but Robert Acquafresca sealed victory for the visitors when he fired home with just five minutes of normal time remaining.
Inter dominated the early exchanges but were made to pay for profligacy by a Bologna counterpunch, with Diego Perez setting up Di Vaio for the opening goal after 37 minutes.
The former Italy international extended the lead moments later after pouncing on a defensive error to slot in his second and give his side a 2-0 half-time lead.
Inter continued to battle but were left open to the counterattack in the second half and Bologna put the game beyond doubt when Acquafresca fired home from the edge of area.
Inter, who have taken one point from the last 15 available, drop to sixth in the standings, while Bologna climb one place to 16th.
An Edison Cavani brace and Ezequiel Lavezzi strike gave Napoli a 3-0 win over Fiorentina in Friday's other match.
Uruguay international Cavani opened the scoring after just three minutes at Stadio Artemio Franchi before doubling up 10 minutes after the break.
Argentine Lavezzi struck in injury time to seal a second consecutive win for Walter Mazzarri's side, which takes them into fifth place.
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