While planning a winter getaway to Chicago seems a little risky, don't let the threat of freezing temps and high winds scare you. I recently spent a long weekend visiting friends in Chicago and the city did not disappoint.

My childhood (and adult) best friend Ashley has family in the city and when she and her husband decided to make a trip after the holidays, I knew I had to tag along. Luckily, they agreed to let me and our friend Pam join the fun.

The weekend was heavily focused around food, drink and family and I was definitely on board with the plan.

We had a delayed flight and started off the trip with some late-night burgers at Kumas Corner. It's a heavy metal kind of place with crazy toppings stacked high between pretzel buns. And luckily for me, you can substitute any beef patty with grilled chicken or a garden burger. I don't have a picture because it was so dark, but the restaurant definitely deserves a mention.

Saturday morning brunch at Cindy's Rooftop may have been my favorite part of the weekend. The family-style menu including chilaquiles and Nutella pancakes was everything I could've hoped for. Aside from good food, the main attraction of Cindy's is the rooftop view of Millennium Park and Lake Michigan.