Asparagus Chicken Roll-Ups with Roasted Acorn Squash

I have finally solved a problem I had been having with my chicken roll-ups. Before, I would cut one chicken breast in half horizontally (because chicken boobs are so big nowadays!) and try to make roll-ups out of those two pieces. Inevitably, I would have a hole in one of the chicken pieces. Frustration would set in. But I have found a solution! Ready? Use 2 chicken breasts!! I know, I'm a genius. Even though using 2 chicken breasts is a whole lot of meat, it is just so much easier to handle. And if there's leftovers, who cares? Just have them for lunch the next day. I don't know why I was stressin' over extra chicken. Silly. Anyway, here's what I did...

-2 chicken breasts (or one per person)
-1 bunch of asparagus (To remove the woody ends of the asparagus, hold one by both ends. Slowly move your hands closer together and let the asparagus naturally break. Discard the end. Then line up that asparagus with the rest of the bunch and cut the rest of them that length.)
-3 oz prosciutto (it's a type of dry-cured ham. Although you can use regular ham, I highly recommend trying this. It just lends a salty depth of flavor that is really different from regular ham.)
-sliced provolone cheese
-1/2 cup of balsamic vinegar
-1 TBS of brown sugar
-1 acorn squash, halved and seeds removed

Preheat the oven to 350. 


Place acorn squash cut side down onto a cookie sheet. Place it in the oven and cook for 40-45 minutes. Meanwhile, remove any fat from the chicken, then place the chicken breast between 2 pieces of plastic wrap. Take a meat mallet (use the smooth side), rolling pin or heavy bottomed skillet and evenly pound the chicken out until it's about 1/2 inch thick. Repeat for all the chicken breasts. Next, salt and pepper both sides of the chicken. Then take a piece of cheese and place a piece of prosciutto on top. Next, add about 5 thin asparagus spears (or 3 thicker ones) on top of the prosciutto. Roll the asparagus spears, prosciutto and provolone cheese into a little bundle. Place the cheese bundle onto the smallest end of the chicken and roll towards the big end. Secure the seam with toothpicks. Repeat until all of your cheese bundles are rolled into your chicken breasts. In a saute pan, over medium heat, add 1 TBS of extra virgin olive oil. Without crowding, brown the outside of the chicken breasts, 2-3 minutes per side. Transfer to a cooling rack set over a cookie sheet. Once all of the chicken breasts are browned and are on the cookie sheet, place it in the oven and cook for 20-25 minutes or until the chicken juices run clear. While the chicken is cooking in the oven, combine the balsamic vinegar and brown sugar in a small sauce pot. Bring to a simmer over medium heat and let simmer for about 10 minutes or until slightly thickened. (Make sure to have your ventilation fan on above the stove as the vinegar can be pretty pungent as it simmers.) To serve, place the chicken breast on a plate and drizzle with the balsamic glaze. For the squash, add butter, brown sugar and cinnamon in desired amounts. 

This meal was very good. I loved the combination of flavors in the chicken. The asparagus was still crisp and green and the flavors of the prosciutto and cheese melted together to create a rich, deep flavor. And the ends of the prosciutto that were sticking out of the chicken were crispy and salty. There was a lot of flavor and texture going on in that moist chicken breast. :)


I was so happy that I finally found a way to do this because chicken roll-ups can be a lot of fun. You can put anything in the chicken breast. They always say that chicken is a blank canvas and it really is. It goes with everything. I'm planning a chicken roll-up dish next week that will have sort of a spinach-artichoke dip in the middle. There are endless possibilities. I'd love to hear any flavor combinations that you come up with! :) Enjoy!