One of my friends i met while I was in the Peace Corps in Ghana was getting married, so we booked a round trip flight from Los Angeles (LAX) to Chicago (MDW) for 30K Southwest points. Then Moo added me using her Companion Pass for $5.60 each way.
After learning how to book flights with points I had looked into booking hotels too, and on this trip we used points to book 3 nights at The Gwen in downtown Chicago because it was walking distance to the wedding. We used 24K SPG point (8k/nt). So after using points we were only out of pocket about $10 on this trip before food/drinks/activities.
We went on the sunset architecture cruise, ate at some delicious restaurants, had some cheap beers with some of my friends I havent seen since Peace Corps, and had a great time at the wedding.