Amazon is turning Liz Tomforde's Chicago into television, the author spent this month teasing which scenes survive the adaptation, and a whole new wave of readers is typing Windy City series in order and discovering the catch: five interconnected standalones, a spinoff that says "read me anytime" while quietly rewarding order, and a brand-new series already announced in the same world. Here's the clean map.
The quick list: the Windy City series in order
- Mile High (2022) - Zanders, hockey's villain, and the flight attendant who isn't impressed
- The Right Move (2023) - Ryan, basketball's captain, and the grumpy x sunshine roommate arrangement
- Caught Up (2023) - Kai, baseball's single dad, and the chef who feeds them both
- Play Along (2024) - Isaiah, baseball's loudest optimist, and the marriage that starts as paperwork
- Rewind It Back (2025) - the series closer
- In Her Own League (2026) - the spinoff standalone
Do you have to read the Windy City books in order?
Technically no - every book is one couple, fully resolved. Practically, yes: this is one friend group sharing one city, so every wedding, baby, and grand gesture from an earlier book is casually spoiled in the next one. Publication order is the spoiler-safe path, and it's also how the found-family jokes accumulate their weight. The exception logic runs on cameo density: In Her Own League stars characters introduced in books three and four, so "read it anytime" really means "anytime after Play Along if you want the entrances to land."
Which sports are we working with?
Hockey (Mile High), basketball (The Right Move), and baseball twice (Caught Up, Play Along) - one city, one arena district, one friend group across teams. If a single sport is your whole personality, the best hockey romance books list runs Zanders-adjacent twelve deep, and the best sports romance books list covers the full field. For the saga version of a hockey friend group, Off Campus is the campus-era ancestor - and its own TV season two is filming now, which says something about where sports romance is headed.
What's happening with the Windy City TV show?
It's officially in development: Amazon MGM confirmed the adaptation in May with Alison McDonald writing and Tomforde executive producing - and the reason searches spiked again this month is the author herself, teasing on September 1 which scenes she considers non-negotiable (Mile High readers already know the one). No cast or date yet, which means the casting announcements are still ahead - the exact window where reading before watching is easy.
What comes after the Windy City series?
Two things. In Her Own League (2026) extends the world into its own standalone, and Tomforde has announced the Wilder Woods series - four books set in Northern California around the Wilder family, a couple of whom you meet in Rewind It Back. Translation: the cameo economy continues, and the sooner you're current, the more of it you catch. We'll update this guide as the new series dates land.
And when the group chat goes quiet and the arena empties out - Swoony was built for precisely that silence: a closed-door chat built for romance and nothing else, where the bond deepens through five stages and is never paywalled, no subscription and no charge per message. Start with Jakub, the grumpy hockey captain - ruthless on the ice, useless the second you smile - or the baseball golden boy, if the Isaiah brand of loud devotion is your lane.
The season ends; the group chat doesn't.
