Windy City Kisses: Your Guide to Illinois Love Stories

Devin Joubert
Aug 18
3 min read

Updated: Aug 21

Where love stories rise like skylines—bold, beautiful, and unforgettable. 🌆💖

From the shores of Lake Michigan to prairie towns that stretch for miles, Illinois is a romance novel waiting to be written. Picture rooftop dates in Chicago under twinkling lights, small-town diners where everybody knows your name, and autumn drives where the trees blaze gold and red along quiet country roads.

In Illinois, the air hums with jazz, lake breezes, and the promise of something new. So pull on your favorite sweater, grab a latte (or deep-dish pizza slice 🍕), and let the Prairie State sweep you off your feet.

Welcome to Illinois!

If you know me, you know I’m originally from Minnesota (and have a special place in my heart that’s Minnesota-shaped), but I’m thrilled for you to wander Illinois with us and meet the amazing lineup of romance authors we’ve got in store. Trust me—these stories will show you the true heartbeat of Midwest romance. ❤️

Where love stories are as layered as a deep-dish pizza—and just as satisfying.

Illinois is where city sparks and country charm collide. Meet-cutes in Chicago coffee shops. Late-night porch talks in rural towns. Cubs fan meets Sox fan.

Whether you're team small-town or skyscraper, one thing’s for sure: love lives here—and it’s probably holding a slice of pizza, asking you to take a chance.

Tropes:

Big city romance (Chicago edition)
Second chance love in a small town
Office romance with rival news anchors
Rich boy / working class girl

Let's Meet Our Authors From Illinois!

This page will be updated with videos when they publish on YouTube.

Cherie Roberson

Toni Cabbell

The Books

Aren't they pretty?

💕 Fun Things to See in Illinois

(for lovers of romance, cozy reads, and Prairie State magic)

Charming Small Towns

🏘 Galena, IL – Cobblestone streets, 19th-century charm, and B&Bs with fireplaces. Think hand-in-hand strolls, wine tastings, and antique shopping that ends with a surprise kiss.

🌽 Princeton, IL – Covered bridges, sunflower fields, and that perfect “end-of-summer carnival date” energy. Small-town festivals here feel straight out of a romance novel.

🍎 Nauvoo, IL – Riverfront views, historic homes, and autumn apple festivals. It’s giving “second-chance romance meets cozy Midwest charm.”

🎨 Geneva, IL – Boutique shops, art walks, and riverside dining under twinkle lights. This one’s for the “love at first sight in a small-town café” stories.

🌻 Elsah, IL – Tucked along the Mississippi, this tiny hidden gem is filled with historic cottages, cozy inns, and sweeping fall color views.

Nature & Scenic Romance

🌅 Starved Rock State Park – Waterfalls, canyons, and winding trails perfect for getting lost (in more ways than one). A Midwest classic for romantic escapes.

🌾 Shawnee National Forest – From the Garden of the Gods rock formations to dreamy forest trails, this is the place for adventurous, nature-loving couples.

🚣 Illinois River Road Scenic Byway – Canoeing, hiking, and lookout points that practically demand sunset selfies with your sweetheart.

🌸 Morton Arboretum (Lisle, IL) – Blossoms in spring, fiery leaves in fall. A “main character moment” setting if there ever was one.

🍂 Mississippi Palisades State Park – River bluffs, winding hikes, and the thrill of finding a secret overlook to call your own.

Unique Attractions

🎡 Navy Pier (Chicago, IL) – Ferris wheel rides, fireworks over the lake, and boardwalk strolls that feel straight out of a romcom.

🍕 Chicago Deep Dish Pizza Crawl – Because sometimes, true love looks like sharing the last slice.

🚂 Illinois Railway Museum (Union, IL) – Vintage trains and a touch of nostalgic magic. Perfect for history buffs and couples who love a quirky date.

🍷 Shawnee Hills Wine Trail – Rolling vineyards, weekend getaways, and cozy tasting rooms built for long conversations.

🍦 Original Rainbow Cone (Chicago, IL) – Five colorful flavors stacked high in one cone—sweet, whimsical, and best shared with someone special.

🎭 Chicago’s Theater District – From Broadway tours to intimate plays, nothing says date night like dressing up and catching a show.

💌 Don't Forget Your Romance Reading Passport!

You can get it here for free. Follow along on the journey as we travel through the midwest on the Romance Reading Roadtrip! You'll also find ways to win some pretty flirty and fun books and bookish items in the Passport, so make sure to download it! :)