Originally Posted by
fieldeng
With the Non Stop limitation in place, you are looking at places like Tampa (or other Florida beaches), California, or San Juan. San Juan isn't bad esp if you stay at a nice beach resort like the Ritz Carlton. There is a Courtyard by Marriott on the same stretch of sand.
If you are willing to connect that opens up a few places. The Gulf Coast of Florida (Destin, Sandestin) is open if you connect via DFW to PNS. The connection in DFW is short (leave ORD at 6am arrive in PNS at 11:10am - Then drive an hour east)
Or fly ORD-DFW-VPS.
There are quite a few DFW-VPS flights each day so your connection shouldnt be too long.
If you decide to do Destin, let me know. Ill make you a deal on my Condo