Blame it on BookTok—I wouldn’t have picked up the Windy City series by Liz Tomforde if my feed hadn’t exploded with hype over the release of Rewind It Back, the final book. Suddenly it felt like everywhere I looked there were character edits, quotes, fan theories. So I figured, why not? I decided to read all four books before the last one dropped.
I’d actually read Caught Up ages ago, but barely remembered anything—I wasn’t much of a sports romance reader back then, so I skimmed more than I savoured. This time around, I gave the series a real chance. And honestly? No regrets.
Mile High
There’s something mildly unhinged about willingly entering the emotional arena of a man like Evan Zanders. He’s not just arrogant—he curates it. The man has weaponised charm into a sport more aggressive than hockey itself. But that’s the trap, isn’t it? You go in thinking he’s a caricature: big ego, bigger biceps, probably leaves the seat up. And then he gets serious when it counts, and now you’re reevaluating your life at 35,000 feet.
Stevie is no innocent bystander. She’s practical, professionally unimpressed, and—most importantly—has sworn off athletes. Which makes her the ideal target for Zanders’ relentless need to win. Their early interactions feel like a competition neither of them meant to enter, laced with banter that isn’t flirtation until it suddenly, unmistakably is.
What makes Mile High interesting isn’t just the heat (though there’s plenty of that). It’s how the book lets them annoy each other into vulnerability. Every petty argument, every jab, peels back another layer they didn’t mean to share. It’s messy, and drawn out, and occasionally infuriating. But that’s also what makes the connection believable. Desire doesn’t arrive clean and convenient. It crashes in, makes demands, breaks all your neat little rules.
If you’re looking for subtlety, look elsewhere. If you’re looking for two people who claw their way toward something real—despite the noise, the fame, the baggage—they’re here. Buckle up.
The Right Move
It’s funny how quickly boundaries become suggestions when you’re living with someone you shouldn’t want. Ryan Shay is the poster child for emotional unavailability: disciplined, exacting, and constitutionally allergic to small talk. He’s not unkind, exactly—just so contained it’s almost hostile. When his team questions his leadership because he seems unapproachable, the solution he lands on is so classically masculine it’s almost sweet in its absurdity: get a girlfriend. Project warmth. Borrow some humanity.
Indy Ivers is, inconveniently, the perfect candidate for this borrowed humanity. She’s Ryan’s sister’s best friend—so familiar enough to pass as intimate, but with just enough history to make living together a powder keg. She’s messy where he’s rigid, expressive where he’s locked down, a hopeful romantic in the worst possible environment. It shouldn’t work even as a lie. And yet the best part of the book is watching them realise it does.
Their fake relationship isn’t some cute, easy ruse. It’s two people negotiating space, privacy, vulnerability. Indy needs Ryan to be a shield at a wedding full of history she’d rather avoid. Ryan needs Indy to sell the idea that he’s not as closed-off as everyone knows he is. But neither of them can keep the performance from bleeding. The line between pretend and real isn’t just blurred—it becomes meaningless.
What the story gets right is the discomfort of wanting more than someone says they can give. Ryan is frustrating, yes, but believably so. A man who has no practice with emotional generosity doesn’t suddenly transform. Indy’s refusal to settle for less than the full thing is the real conflict here. It’s not just about proximity or attraction. It’s about asking whether love is even possible with someone who insists it isn’t.
If you’re after something glossy and simple, this isn’t it. This is about the messiness of hoping people can change—while knowing they might not. And whether that hope is enough to stay.
Caught Up
There’s a quiet grief in watching someone who’s forgotten how to enjoy his own life. Kai Rhodes is a man divided—between the field and fatherhood, between control and exhaustion, between who he used to be and who he’s trying to become. He’s a single dad and a star athlete, yes, but Caught Up is never really about fame or talent—it’s about care. The kind you give out, the kind you deny yourself, and the kind that arrives when you’re least ready for it.
Enter Miller Montgomery, a pastry chef at the peak of her career but unable to create anything new. She’s burned out, uninspired, and hiding it behind sugar and sarcasm. Her father, who also happens to be Kai’s coach, forces a pause on her career by sending her into the Rhodes household for a summer job she never asked for. What’s meant to be a reset—for both of them—quickly becomes a challenge neither expected. Miller isn’t built for stillness, and Kai doesn’t know how to let anyone close.
What unfolds between them is slow and unusually tender. This isn’t a whirlwind romance or a fake dating setup; it’s proximity wearing down two people who don’t know how to ask for what they need. The relationship between Miller and Kai’s son is just as affecting as the one between her and Kai—perhaps more so, at first. Watching her stumble into maternal affection without meaning to, and watching Kai war with his own guilt and longing as he sees it, is where the book starts to deepen.
The central question here isn’t will they fall in love? Of course they will. It’s can love be enough when time is working against you? Because Miller is a runner—she says so herself. She leaves before things get serious. Kai, meanwhile, doesn’t believe he deserves softness. He’s a man who thinks he has to choose between protecting his son and wanting things for himself. She’s a woman who’s never learned how to stay.
That’s where the ache of this book lives: in the in-between. The way love arrives too soon or too late. The way responsibility crowds out desire. The way people learn to unlearn the stories they’ve told themselves about who they are.
The story is about a summer that shouldn’t have meant anything, and ends up meaning everything. It’s about joy and hesitation, grief and second chances. And most of all, it’s about the kind of love that asks you to stay when everything in you wants to run.
You’ll know exactly where it’s going. But that’s not the point. The point is how honestly it gets there.
Play Along
Some marriages are built on shared values. Some on timing and compromise. Kennedy and Isaiah’s starts with cheap Vegas liquor, a blackout blur, and a marriage certificate they can’t immediately undo. It’s not romance so much as damage control at first—a problem to be managed, spun into something believable enough to save Kennedy’s job. She’s the only woman on staff for Chicago’s baseball team, already fighting to be taken seriously in a male-dominated world. A scandal? Career suicide.
Isaiah Rhodes is the exact wrong man for a PR-friendly solution. He’s impulsive, irreverent, and dangerously charming, with the cocky certainty of someone who’s used to getting what he wants—except Kennedy. She’s always been off-limits, frustratingly professional, immune to every attempt he’s made to break through that boundary. Until Vegas breaks it for them.
What follows isn’t the predictable fallout of a drunken mistake, but something messier and more interesting: two people forced to share space and public roles they didn’t choose. Kennedy isn’t just cautious—she’s deeply wary of being seen as anything less than perfect at work. She’s a woman forced to hold the line so men stop questioning if she belongs at all. Isaiah isn’t trying to sabotage that. In his own unfiltered way, he’s trying to prove he’s safe to want.
Their deal—to stay married for a season—starts as a calculated lie but refuses to stay that clean. Lines blur in the way they talk, fight, want. The book knows the appeal of forced proximity and banter, sure, but it’s also keenly aware of what it means to be a woman who can’t afford a scandal, and a man willing to risk his own reputation for hers. Isaiah isn’t the problem Kennedy fears—her fear is that he’s the exception, the one risk she actually wants to take.
Play Along isn’t about easy love. It’s about the performance of respectability in a world that doubts you, and the terror of realising someone might actually see you behind it. It’s funny, exasperating, sometimes over the top in that classic forced-marriage trope way, but grounded by two people who are both so sure they shouldn’t want this, and can’t seem to stop anyway.
If you’re looking for a polished, low-stakes rom-com, this probably isn’t it. But if you’re into watching a marriage built backwards—starting with the paperwork and working its way toward the truth—there’s something here that feels unexpectedly real.
Overall, the Windy City series is exactly what sports romance fans hope for—and sometimes even more. Each book brings its own trope-driven fun, from fake dating to forced proximity to second-chance heartbreak, but Liz Tomforde grounds them in characters who feel layered and real. Across four books, you see teammates become family, hookups become forever, and love stories that don’t shy away from the mess of timing, ego, or vulnerability.
It’s not just about the heat or the banter (though you’ll get plenty of both), but about people figuring out how to choose each other—again and again. And for me, that’s what makes this series worth reading. Whether you’re a die-hard sports romance reader or just looking for well-done contemporary love stories with big feelings and big-city energy, Windy City delivers.
If you’ve been on the fence about picking up the series, consider this your sign to dive in. You just might find yourself falling for these Chicago athletes—and their complicated, heartfelt romances—the same way I did.