Pesto Chicken Rollups

I’m on a constant search to find ways to add lots of flavor and zing to the open canvas that is chicken breast and according to Adam Carolla and everyone on the show, I hit the bullseye with this one!

This was inspired by a tray of pinwheel sandwiches I was asked to bring to a preschool meeting. I loved how pretty they looked and how much people seem to enjoy them. But was there a way to “elevate” this idea for a nice dinner and of course make it grain-free?

I figured I’d try this idea with thinly-pounded chicken breast smothered in delectable pesto.

But what to roll inside it? I wanted something with a mediterranean flair but nothing that would overpower the pesto. I landed on artichoke hearts and cherry peppers (pimentos) and this seemed to be a winning combo.

Let’s give this wonderful meal a try, shall we?


  • 4 chicken breast pounded thin (I use Butcher Box)
  • Pesto (My link for a wonderful pesto is right here!)
  • 1/2 cup artichoke hearts,  quartered
  • Small jar of diced pimentos
  • Kitchen tools: toothpicks or skewers (optional), baking sheet, Silpat or parchment paper, meat tenderizer or rolling pin, ziplock bag to pound chicken, food processor (for the pesto).


  1. Preheat oven to 375 degrees

  2. Place as many chicken breasts into large ziplock that fit comfortably and pound thin using the flat meat tenderizer or a rolling pin.

  3. Lay thinly pounded breasts on lined cookie sheet and spoon pesto onto each side of chicken. (IMPORTANT NOTE! In order to avoid cross-contamination from raw chicken, pour 1/2 of pesto into a separate bowl that you will use ONLY for raw chicken.)

  4. Once both sides of chicken are coated, place 3 strips of artichoke hearts and a small spoonful of pimento peppers onto the tip chicken and roll chicken until it resembles a croissant-shape.

  5. Repeat with each piece.

  6. Pop in the oven for 30-40 minutes, checking periodically to make sure top doesn’t burn and chicken is cooked to an internal temp of 165 degrees.

  7. Either finish in the broiler for a slightly charred top (about 30-60 seconds) or take out of the oven, let the chicken rest for 5 minutes, then garnish with a little more pesto and parmesan and serve!


Since chicken breast doesn’t have much flavor on its own, you can marinate the chicken in the pesto for a few hours – or even overnight – so the flavors really absorb into the chicken. (Don’t worry if you don’t as it’ll still be plenty flavorful!)

These rollups are even better as leftovers! And I have science to back this up! So make these for weekly meal prep or make them the night before your dinner party and warm in the oven as your guests arrive. This goes for almost all the recipes I post!

Get creative with the veggies, cheeses or meats you roll inside! Asparagus, sun-dried tomatoes and spinach are other great options.

My trick with the artichokes hearts is to buy the marinated ones and wash about half the brine off. That way, they have a hint of flavor without competing with the pesto!

I didn’t end up needing skewers or toothpicks to keep my rolled up chicken in place but I had them on hand just in case. If you pound the chicken into a large enough surface, they hold well on their own with no problem!

Disclosure – I’m lucky enough to partner with Butcher Box on the Adam Carolla Show and Easy Listening. I receive compensation to promote their product and it’s a product I absolutely believe in!


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