The Windy City Series in Order

About the Windy City series

Series Premise

The series follows the high-profile, high-pressure lives of Chicago’s professional athletes (basketball and baseball players) as they navigate fame, injuries, team dynamics, and the public eye while falling in love with strong, independent women who challenge their guarded hearts. Each book features a different athlete from the Chicago Devils (NBA basketball team) or Chicago Cubs (MLB baseball team), with romance tropes like: > Fake dating / marriage of convenience > Enemies-to-lovers > Grumpy-sunshine > Forbidden or off-limits relationships > Second chances or forced proximity The stories blend intense sports drama (games, trades, injuries, team rivalries) with emotional depth (family issues, past trauma, mental health, self-worth) and steamy, passionate romance.

Main Characters

The series rotates protagonists from Chicago’s pro sports world, with frequent crossovers among teammates and their partners:
> Ryan Shay (The Right Move, Book 1) — Star NBA point guard for the Chicago Devils; grumpy, guarded, and deeply private. Falls for his brother’s ex-fiancée in a fake-dating arrangement.
> Indy Ivers — Heroine of Book 1; bright, bold, and resilient; Ryan’s fake girlfriend who becomes real.
> Zanders (Mile High, Book 2) — Cocky, charismatic NHL defenseman (Chicago hockey team); known for his playboy reputation.
> Stevie Shay — Ryan’s sister; heroine of Book 2; flight attendant who clashes with Zanders.
> Isaiah Rhodes (Play Along, Book 3) — Baseball player (Chicago Cubs); charming but emotionally closed-off.
> Kai — Heroine in Book 3; strong, independent woman tied to Isaiah’s world.
> Rio — Another athlete (later book); intense and loyal.
> Recurring: The Chicago Devils and Cubs teams, family members (especially Ryan and Stevie’s siblings), and the tight-knit group of athletes and their partners who form a found-family dynamic.

Setting

Modern-day Chicago, Illinois (with a strong Windy City vibe):
> United Center (Chicago Devils NBA arena), Wrigley Field (Cubs baseball), team facilities, and luxury downtown apartments.
> Chicago streets, bars, restaurants, rooftops, and Lake Michigan views.
> Road trips for away games, team events, and occasional escapes to cabins or other cities.
The atmosphere is vibrant and urban — big-city energy, sports culture, cold winters, summer lake life, and the glamour of professional athletics.

Tone & Themes

Steamy, emotional, and addictive — classic sports romance with high heat (explicit love scenes), witty banter, angst, and heartfelt moments. The tone is passionate, funny, and uplifting, balancing the chaos of professional sports with tender, healing love stories. It includes humor (team banter, player antics), vulnerability (heroes opening up), and strong empowerment for heroines — feel-good and swoony, with a touch of real-life struggles (injury, pressure, family drama) but always ending in hopeful, satisfying HEAs.

The series is hugely popular (especially on BookTok) for its hot athletes, strong heroines, witty banter, emotional depth, and addictive sports-romance tropes — ideal for fans of sports romance like Elle Kennedy (Off-Campus/Briar U), Helena Hunting, or Teagan Hunter. It has mature content (explicit romance, some light drama/trauma).