The Windy City

At the end of April my best friend and I kissed our beautiful families goodbye and headed to the airport to begin our first girls trip. I have traveled a bit, but she typically visits family when she has time off, so when I remembered her dream trip would be to visit Chicago I figured, Why not? So Chicago it was. We both hoped the weather would be nice, not too hot, not too cool, and started exchanging ideas about what the trip would entail.

This is vital to a trip taken with friends: find out what everyone wants to do while you're away and do a nice mix of everything so the trip is fulfilling to all involved. I've only traveled with a large group once, but that was pretty easy because there were so many of us it seemed half went one way and half went the other. It worked. But when there are just two of you, if one wants to just hit the party scene and the other wants to sight-see, well it could get ugly.

As the trip got closer I wondered what kind of travel companion my besty might be: would she want to be up and at 'em bright and early, or lay in bed til noon before we hit the town? Would we get a chance to relax before returning home to our respective duties or would we go full-throttle the whole time? I'm the kind of girl who likes to relax a little after spending a day or so on the town and I was really hoping she would be down with that.

Turned out we were very much on the same page, probably because we were so excited about our trip that we talked about it every chance we got. We made compromises: she wanted to take a boat tour, I was skeptical, but we did it and I enjoyed it! I'm not sure it was a compromise on her part, but we walked downtown Chicago and whatever we wanted to see, we saw, whatever we wanted to eat, we ate. All while walking kind of aimlessly up and down Chicago streets. I loved the spontaneity of it, and it only worked for me because it was just us girls.

When I'm traveling with the fam, I like to make sure we hit everything we all want to do because with four different ideas of fun, it's easy to inadvertently miss someone's request. I'm a planner, the family travel planner in fact. Tell me where we're going and I'll find plenty for us to do. For Chicago, we planned a couple of things and flew by the seat of our pants for the rest.

There is something to be said about traveling with a girlfriend. You know the ins and outs of why you both need a break, you both care about your family and issues you both face, and when it is all said and done you both know you will look out for each other.