If you love sports romance, strong chemistry, witty banter, found family, emotional stories and plenty of spice, the Windy City series by Liz Tomforde deserves a place on your TBR.
Set around the world of professional sports in Chicago, the series follows different couples across five interconnected books. Each book has its own central romance, while familiar characters and friendships continue throughout the series.
The main Windy City series currently consists of five books, beginning with Mile High and ending with Rewind It Back. Liz Tomforde’s official website also lists In Her Own League as a Windy City spin-off.
So, if you’re wondering “What order should I read the Windy City series?”, we’ve got you covered.
Windy City Series Reading Order
The best way to read the main series is in publication order:
1. Mile High – Book 1
2. The Right Move – Book 2
3. Caught Up – Book 3
4. Play Along – Book 4
5. Rewind It Back – Book 5
This order lets you experience the characters, friendships and interconnected storylines as they develop throughout the series.
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1. Mile High
Windy City Book 1
Welcome to Chicago hockey.
Mile High introduces readers to Evan Zanders, an NHL star with a reputation for being arrogant, confident and impossible to ignore, and Stevie, a flight attendant who isn’t impressed by his attitude.
Stevie has made a promise to herself about never getting involved with another athlete. Unfortunately, working aboard the Chicago hockey team’s private plane means spending plenty of time around Zanders.
Their relationship starts with plenty of tension, arguments and undeniable chemistry.
What begins as an attraction neither of them wants to admit slowly develops into something much deeper.
Tropes & vibes:
– Sports romance
– Hockey romance
– Enemies-to-lovers energy
– Forced proximity
– Workplace romance
– Banter
– Spice
– Found family
If you love hockey players, confident MMCs and a romance filled with tension, Mile High is the perfect place to start.
Liz Tomforde describes it as the story of an NHL playboy who learns about love after meeting the newest flight attendant on his team’s private plane.
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2. The Right Move
Windy City Book 2
If Mile High got you hooked on the Windy City world, The Right Move is where things get even more addictive.
This time, the story follows Ryan Shay, an NBA superstar, and Indy, his sister’s best friend.
When Indy needs somewhere to stay, Ryan unexpectedly ends up sharing his home with her.
Living under the same roof creates plenty of opportunities for awkward moments, emotional tension and chemistry that becomes increasingly difficult to ignore.
What starts as a complicated living situation eventually turns into something neither of them expected.
Tropes & vibes:
– Sports romance
– NBA romance
– Forced proximity
– Best friend’s brother
– Roommates
– Fake dating
– Slow-burn chemistry
– Found family
– Spice
Ryan Shay quickly became one of the most talked-about characters in the series among romance readers, making The Right Move a favorite for many fans.
Liz Tomforde’s official description centers on an NBA superstar who has to open both his home and his heart when his sister’s best friend has nowhere to live.
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3. Caught Up
Windy City Book 3
Next comes Caught Up, which takes readers into the world of professional baseball.
This book follows Kai Rhodes, a successful MLB pitcher and single dad, and Miller, who becomes his daughter’s nanny.
Kai is used to controlling his life, his career and his responsibilities as a father.
Miller brings something completely different into his world.
As they spend more time together, their relationship develops from an unexpected arrangement into something much more meaningful.
And, of course, falling for someone when you’re trying to keep everything under control is never simple.
Tropes & vibes:
– Sports romance
– Baseball romance
– Single dad
– Nanny romance
– Forced proximity
– Family
– Emotional romance
– Found family
– Spice
One of the biggest strengths of Caught Up is that the story isn’t only about the romance. Family relationships and friendships also play an important role.
Liz Tomforde describes the book as the story of a single-dad MLB pitcher who has to learn to loosen up when his coach’s daughter becomes his new nanny.
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4. Play Along
Windy City Book 4
Get ready for another sports romance with a completely chaotic setup.
Play Along follows Isaiah Rhodes, an MLB shortstop, and Kennedy, the team’s athletic trainer.
After a wild night in Vegas, they wake up married.
Yes. Married.
The problem?
This isn’t exactly the kind of relationship either of them planned for.
What follows is a fake-marriage situation filled with forced proximity, unresolved feelings and plenty of chemistry.
Tropes & vibes:
– Sports romance
– Baseball romance
– Fake marriage
– Forced proximity
– Friends-to-lovers vibes
– Workplace romance
– Mutual feelings
– Spice
– Emotional moments
If you love “we accidentally got married” romance stories, Play Along is going to be difficult to put down.
According to Liz Tomforde’s official description, the story follows an MLB shortstop who has to prove he’s husband material after waking up in Vegas married to the woman he’s always had feelings for.
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5. Rewind It Back
Windy City Book 5
The fifth main book in the series brings readers back to the world of hockey.
Rewind It Back follows Rio DeLuca and Hallie, whose story is filled with history, unresolved feelings and second-chance romance.
Hallie was once an important part of Rio’s past.
Now she’s back in his life—and things become even more complicated when she moves in next door and takes on the job of renovating his house.
Sometimes the person you never truly got over is the person you can’t escape.
Tropes & vibes:
– Sports romance
– Hockey romance
– Second chance romance
– Childhood connection
– Forced proximity
– Neighbors
– Past feelings
– Emotional romance
– Spice
Liz Tomforde describes Rewind It Back as the story of an NHL star forced to confront his past when the only girl he’s ever loved moves in next door.
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Is the Windy City Series Connected?
Yes!
Each book focuses on a different main couple, but the books take place within the same interconnected world.
Characters from previous books can appear in later stories, and friendships and relationships continue throughout the series.
That’s one of the reasons readers often recommend reading the books in order.
You don’t necessarily need to know every detail from the previous book to understand the next romance, but reading the series from Mile High onward makes the character connections much more enjoyable.
What Makes the Windy City Series So Popular?
There are plenty of sports romance books out there, but the Windy City series stands out because it isn’t only about athletes falling in love.
Liz Tomforde combines romance with:
🏒 Professional Sports
Each story gives readers a different look into professional sports, from NHL hockey to NBA basketball and MLB baseball.
❤️ Strong Romantic Chemistry
The couples have plenty of banter, attraction and emotional tension. If you enjoy romance where the chemistry is obvious from the beginning, this series is worth checking out.
👨👩👧 Found Family
Friendships and family relationships are an important part of the series. The characters don’t exist in isolation—their relationships with the people around them make the world feel connected.
😂 Witty Banter
If you love couples who constantly tease, argue and challenge each other, you’ll find plenty of that here.
🌶️ Spice
The series is known for combining emotional romance with steamy scenes, making it popular among adult contemporary romance readers.
🥹 Emotional Moments
Behind the attractive athletes and romantic tension, these books also explore family, insecurity, grief, personal growth and complicated relationships.
What Order Should You Read the Windy City Series?
If you’re starting the series for the first time, follow this order:
1. Mile High
🏒 Hockey romance
2. The Right Move
🏀 Basketball romance
3. Caught Up
⚾ Baseball romance
4. Play Along
⚾ Baseball romance
5. Rewind It Back
🏒 Hockey romance
This is the complete five-book main series order.
Liz Tomforde’s website also lists In Her Own League as a Windy City spin-off, so readers who want to continue exploring the world can look out for that story as well.
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Which Windy City Book Should You Read First?
If you’re completely new to Liz Tomforde, start with Mile High.
It introduces the world and gives you the foundation for the interconnected characters.
But if you’re choosing based on tropes:
Love hockey + enemies-to-lovers?
→ Mile High
Love best friend’s brother + forced proximity?
→ The Right Move
Love single dads + nanny romance?
→ Caught Up
Love fake marriage + baseball romance?
→ Play Along
Love second chances + childhood connections?
→ Rewind It Back
The best part? You don’t have to choose just one.
Read the whole series.
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Final Thoughts
The Windy City series by Liz Tomforde is a must-read for anyone who loves contemporary romance mixed with professional sports, banter, found family, emotional moments and plenty of chemistry.
From Zanders and Stevie in Mile High to Rio and Hallie in Rewind It Back, every book brings a different couple and a different romance trope while keeping the larger world connected.
If you’re building your next romance TBR, this is one series that’s hard to ignore.
So grab your favorite drink, clear your weekend and get ready for five books full of athletes, romance, drama, banter and unforgettable couples. 📚❤️
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Frequently Asked Questions
How many books are in the Windy City series?
There are currently five main books in the Windy City series: Mile High, The Right Move, Caught Up, Play Along, and Rewind It Back.
Do I need to read the Windy City books in order?
It’s recommended. Each book follows a different couple, but the characters and their world are interconnected. Reading in publication order gives you the best experience.
What is the first Windy City book?
The first book is Mile High, featuring an NHL hockey player and a flight attendant.
What genre is the Windy City series?
The series is primarily contemporary sports romance, with elements of found family, humor, emotional romance and spice.
Who wrote the Windy City series?
The series was written by Liz Tomforde, a romance author known for contemporary romance featuring sports, witty banter, found family and plenty of steam.
Is Windy City a standalone series?
The five main books form an interconnected series, with each book focusing on a different couple. Liz Tomforde also lists In Her Own League as a Windy City spin-off.
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Ready to Start the Windy City Series?
If sports romance, handsome athletes, strong female characters, addictive chemistry and found family are your kind of romance, the Windy City series belongs on your bookshelf.
📚 Shop the Windy City Series at Bookshop99 and find your next romance obsession.
Bookshop99 — Build your library. Find your next obsession. ❤️
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