Okay, we need to settle the debate: Cinnamon rolls and chili? Yes or no?
If you’re from the Midwest, you probably just nodded your head aggressively. If you aren’t, you might be looking at me like I’m crazy. But trust me, there is a reason that sweet, yeasty dough works so well with savory tomato and beef.
But if you aren’t quite ready to dip your breakfast pastry into your dinner bowl, don’t worry. I’ve got plenty of other options that fit the cozy, comfort-food vibe of chili night perfectly.
From the “sopapilla” cheesecake that vanishes at every Super Bowl party I host to the refreshing zing of a Key Lime Pie, here are 10 desserts that deserve a spot on your table.
Creamy & Cooling
1. Sopapilla Cheesecake Bars
If you have never experienced the magic of sopapilla cheesecake, you are honestly missing out on a life-changing event.
It combines the tangy creaminess of cheesecake with the cinnamon-sugar crunch of a fried sopapilla, but without the hassle of actually frying anything. It is the ultimate Tex-Mex dessert hack.
You start by layering store-bought crescent roll dough on the bottom of a pan (‘cause who has time for homemade dough on chili night?) and topping it with a rich cream cheese mixture. Then you seal it with another layer of dough and drown the whole thing in butter, cinnamon, and sugar before baking.
I served these at a Super Bowl party last year, and I kid you not, the pan was licked clean before halftime. The way the pastry puffs up creates these hollow, sugary pockets that are just addictive.
2. Classic Tres Leches Cake
When your mouth is on fire from a spicy bowl of chili, nothing puts out the heat quite like a cold, milk-soaked sponge cake. Tres Leches is dense, moist, and incredibly refreshing because it is served straight from the fridge.
The key here is patience. After you bake the sponge cake, you have to poke holes all over it and slowly pour over the mixture of evaporated milk, sweetened condensed milk, and heavy cream. You want that liquid to soak into every single crumb.
My aunt always says the secret is letting it sit overnight. Trust me on this one, the flavor gets significantly better the longer it sits, so it is the perfect make-ahead dessert for when you are busy prepping the main course.
3. “Fried” Ice Cream
Okay, fair warning, actual fried ice cream is a pain to make at home, but this “unfried” version gives you all the crunch without the hot oil danger. It is playful, looks impressive, and brings that restaurant vibe right to your kitchen table.
You basically roll scoops of vanilla ice cream in a toasted mixture of cornflakes, cinnamon, and sugar. The trick is to crush the cornflakes pretty fine so they adhere to the ice cream, creating a solid shell that cracks when you dig in.
I made these for a taco Tuesday that turned into a chili night, and the contrast between the hot, savory soup and the frozen, crunchy dessert was unreal. Don’t forget to drizzle honey on top.
Cinnamon & Spice
4. Homemade Cinnamon Rolls
If you are from the Midwest, you already know that chili and cinnamon rolls are a non-negotiable pair. For everyone else giving me a weird look right now, just try it once. The yeasty, sweet dough balances out the savory acid of the tomato and beef perfectly.
Making these from scratch takes a little time, but the fluffiness you get is worth the wait. You want to make sure you don’t roll the dough too tightly, or the centers will pop up while baking like little volcanoes.
My college roommate introduced me to the concept of dipping the roll into the chili. I was skeptical at first, but now I can’t eat a bowl of red without a warm, gooey roll on the side.
5. Homemade Churros
There is something so festive about a stack of churros, especially if your chili has a bit of a spicy kick. These ridged sticks of fried dough are rolled in cinnamon sugar and serve as the perfect vessel for chocolate sauce or dulce de leche.
You will need a piping bag with a star tip to get those classic ridges, which are crucial because they hold onto more sugar. Fry them until they are golden brown and listen for that hollow sound when you tap them.
I usually set up a little dipping station with different sauces when I make these. Watching my friends argue over whether chocolate or caramel is the superior dip is almost as fun as eating them.
The Chocolate Fix
6. Classic Texas Sheet Cake
This cake is an institution in the South for a reason. It is huge, it is rich, and it feeds a crowd, making it the ideal partner for a big pot of chili. Plus, the ratio of icing to cake is basically 50/50, which is how it should be.
The defining feature of this recipe is the boiled chocolate icing that you pour over the cake while it is still warm. It creates a fudgy, slightly crackled top layer that locks in all the moisture.
I brought this to a church potluck once, and three different people asked me for the recipe before I even left the building. It is impossible to mess up, even if you aren’t a confident baker.
7. Mexican Hot Chocolate Brownies
Why serve regular brownies when you can serve brownies that kick back? These fudgy squares include a pinch of cayenne pepper and cinnamon, echoing the spices in your main dish while providing a serious chocolate fix.
Be careful with the cayenne. You want a subtle warmth that hits the back of your throat after the sweetness, not an immediate burn. Start with less than you think you need if you are nervous.
Honest confession, I sometimes use a boxed mix and just doctor it up with spices when I am short on time. Nobody has ever noticed, and the result is still gooey, spicy perfection.
Fruity Palate Cleansers
8. Classic Key Lime Pie
Sometimes you just need to cut through the heavy, meaty richness of chili with something sharp and citrusy. Key lime pie is the ultimate palate cleanser, offering a tart punch that wakes up your taste buds.
The reaction between the lime juice and the sweetened condensed milk is what thickens the filling, so you don’t need to rely on flour or cornstarch. A graham cracker crust is traditional, but a gingersnap crust adds a nice spicy depth.
I love serving this because it looks so elegant with barely any effort. A dollop of whipped cream and a slice of lime on top makes it look like you bought it from a fancy bakery.
9. Lemon Bars
These are sunshine in bar form. The buttery shortbread crust provides a sturdy base for the gooey, tart lemon filling. They are easy to pick up and eat with your hands, which keeps the casual vibe of a chili night going.
Make sure you bake the crust slightly before adding the filling, otherwise, you end up with a soggy bottom. And don’t skimp on the powdered sugar dusting at the end; it hides any cracks and adds that necessary touch of sweetness.
My dad claims these are “too sour,” but I catch him sneaking a second piece every single time I make them. The tartness is exactly what you need after a savory meal.
10. Old Fashioned Peach Cobbler
There is a rustic, homey feel to peach cobbler that matches the comfort food energy of chili. Hot fruit bubbling up through a tender biscuit topping is the definition of a hug in a bowl.
You can use fresh peaches if they are in season, but frozen ones work just fine and save you the hassle of peeling. The juice from the fruit mixes with the sugar to create a syrup that is absolutely to die for.
Serve this warm with a scoop of vanilla ice cream melting on top. The way the cold cream swirls into the hot peach syrup is honestly better than the chili itself.