Windy City Bad Boys Books in Order
Part ofMickey Miller Books in OrderBrowse the Windy City Bad Boys books by Mickey Miller in order, with summaries, Chicago setting notes, series background, and easy starting guidance.
Last updated: July 14, 2026
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Windy City Bad Boys books in publication order
2 books
Dirty CEO
by Mickey Miller
2018
Kelly McNamara wants her own future, not a place beside powerful Chicago CEO Vince LaRosa. But Vince has loved her since high school, and their families' Irish-Italian feud cannot quite extinguish their old spark.
Fantasy Island
by Mickey Miller
2018
A professional assignment sends a woman and her sexy new client to a remote island for sixty days. With one room, no easy escape, and attraction they cannot ignore, business quickly becomes personal.
Windy City Bad Boys books in chronological order
Series background & context
The Windy City Bad Boys series is a two-book contemporary-romance collaboration by Mickey Miller and Holly Dodd. The stories move through a tougher, more dangerous version of Chicago than Miller's lighter sports romances, pairing attraction with family history, professional ambition, and the trouble that comes from wanting someone on the other side of an old divide.
The series begins with Dirty CEO. Kelly McNamara has plans and independence of her own, and she does not want to become an accessory to Vince LaRosa's powerful life. Vince is a successful Chicago CEO, but he is also the boy Kelly once knew, the person she kissed under the high-school bleachers, and someone her family has every reason to distrust.
Their families' history is a real obstacle.
Kelly comes from an Irish family shaped by the violence and tension of Chicago's South Side. Vince comes from an Italian family with its own history of conflict. Years have passed, and Vince is no longer the young man Kelly left behind, but the old bad blood has not disappeared. Their romance has the pull of a second chance, while the family feud gives it an edge that goes beyond ordinary workplace attraction.
Fantasy Island shifts the setting away from the city and into a remote-island setup. A woman is sent to work with a new client, only to find that the assignment means sharing close quarters for an extended stay. The island removes the usual escape routes. There is nowhere to hide from the attraction, the arguments, or the inconvenient emotional baggage both characters bring with them.
The title may suggest a carefree vacation, but the series is more interested in the tension between control and vulnerability. Its men are powerful, sometimes intimidating, and used to getting their way. Its women have their own ambitions and do not want romance to erase them. That clash supplies the spark.
Because there are only two books, the series is easy to read in order. Start with Dirty CEO for the Chicago setting, old flame tension, and family-rivalry stakes. Continue with Fantasy Island for a more isolated forced-proximity romance. The books are linked by tone and the authors' shared interest in high-pressure relationships, rather than one single ongoing couple.
Expect adult contemporary romance with heat, emotional complications, and settings that put the characters under pressure. Chicago adds history and danger in the first book. The island adds isolation in the second. In both, the central question is whether the characters can let go of the version of themselves they thought they needed to be.
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