Windy City Series: Discover the Books in Order
If you’ve recently spent time going thru BookTok, BookStagram, or romance forums, you’ve most likely come across the viral Windy City series. Liz Tomforde, an indie publishing powerhouse, wrote this series, which has won the hearts of romance fans, writers, and poets alike.
Set against the vibrant backdrop of Chicago, these interconnected standalone novels deliver the perfect mix of high-stakes professional sports, emotional depth, electric banter, and deeply swoon-worthy romances.
Whether you are looking to dive into the windy city series books for the first time or want to ensure you read them in the optimal chronological sequence, this ultimate guide covers everything you need to know.
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What Is the Windy City Series?
The Windy City series is a contemporary romance book series created by author Liz Tomforde. Set in Chicago, Illinois (famously nicknamed the “Windy City”), each book follows a different couple navigating life, career pressures, past trauma, and fall-in-love moments.
While each story focuses on a different couple and can technically be read as a standalone, the main characters belong to the same close-knit friend group and family network. Because characters from previous books frequently make guest appearances, reading the series in publication order provides the most satisfying character arcs and emotional payoff.
Key Highlights of the Series
- Genre: Contemporary Sports Romance
- Setting: Chicago, Illinois
- Tone: Emotional, humorous, passionate, and character-driven
- Pacing: Slow-burn with high chemical tension
- Themes: Found family, emotional healing, single parenthood, workplace romance, and sports pressure
Windy City Series Books in Reading Order
To get the full experience of the character growth and background lore, here is the official reading order for the windy city series books.
1. Mile High
Main Characters: Zanders & Stevie
Primary Tropes: Flight Attendant x Professional Hockey Player, Enemies to Lovers, Forced Proximity, Banter-Heavy
Mile High kicks off the series with the turbulent romance between Evan Zanders, the bad-boy star player of Chicago’s professional hockey team, and Stevie, a flight attendant on the team’s private plane. Zanders is used to getting whatever and whoever he wants.
However, Stevie is completely immune to his charm and refuses to be another one of his fleeting conquests. Forced together on long flights throughout the season, their sharp banter slowly softens into mutual respect and intense attraction.
Stevie is a fiercely relatable heroine who deals with real-world insecurities regarding body image and self-worth. Zanders’ shift from an arrogant playboy to a devoted partner makes this book a fan favorite for lovers of authentic character development.
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2. The Right Move
- Main Characters: Ryan & Indy
- Primary Tropes: Fake Dating, Roommates to Lovers, NBA Player x Flight Attendant/Baker, Grumpy x Sunshine
Widely regarded by romance fans as a standout in the series, The Right Move follows Ryan Shay, the stoic NBA captain for the Chicago Devils, and Indiana “Indy” Ivers, a free-spirited baker who happens to be the best friend of Ryan’s sister.
When Indy finds herself needing a place to stay after a bad breakup, Ryan opens his home to her as a favor. To appease his team’s PR department and settle family pressures, they agree to a fake dating arrangement that quickly blurs the line between pretense and reality.
3. Caught Up
Main Characters: Kai & Miller
Primary Tropes: Single Father x Nanny, Professional Baseball Player, Forced Proximity, Found Family
Caught Up shifts the spotlight to professional baseball. Kai Rhodes, a single father and star pitcher, is entirely focused on two things: raising his young son, Montgomery, and winning games.
Enter Miller Montgomery, a talented nanny hired to care for Kai’s son during the demanding season. Miller brings warmth, order, and joy back into Kai’s home, causing Kai to rethink the strict boundaries he built to protect his heart.
The bond between Miller and young Montgomery adds an extra layer of sweetness to the narrative, making it an ideal choice for fans of single-parent tropes and emotional family dynamics.
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4. Play Along
- Main Characters: Isaiah & Kennedy
- Primary Tropes: Fake Marriage / Vegas Marriage, Golden Retriever Male Lead, Mutual Healing
Play Along focuses on Isaiah, a charming professional athlete known for his positive attitude, and Kennedy, a woman recovering from past relationship trauma. Following an unexpected trip to Las Vegas, the pair find themselves accidentally married.
Instead of instantly annulling it, they decide to stick together for public relations and personal reasons, eventually discovering that their impulsive decision might be the best thing to ever happen to them.
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Final Thoughts
The windy city series has earned its reputation as a standout contemporary romance collection by combining deep emotional stakes, memorable characters, and satisfying slow-burn storylines. Whether you choose to start with Mile High or jump into fan-favorite The Right Move, you are in for a thoroughly entertaining read.
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Frequently Asked Questions
Do I have to read the Windy City series in order?
While each book follows a different couple and can be read as a standalone, it is strongly recommended to read them in order (Mile High, The Right Move, Caught Up, Play Along). Reading in sequence avoids minor spoilers regarding earlier couples and helps you track the overarching friend group dynamic.
Is the Windy City series suitable for young adult readers?
No. The series is classified as New Adult / Contemporary Adult Romance due to explicit open-door romantic content, mature themes, and strong language. It is best suited for readers aged 18 and older.
Will there be more books in the Windy City series?
Yes. Author Liz Tomforde has indicated plans to continue expanding the universe with additional stories centered around characters connected to the Chicago sports world.
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