MY husband and I were able to get PDX-MDW seats using miles in late June with about a week's notice. We were forced to use the new Elite 30K mile tickets, but at the time the cheapest fares on short notice were around $600 each, and we were also burning leftover Amex points, so it was worth it.....

We've also redeemed miles several other times at the standard 15k per ticket. We've always found them very helpful, friendly, and easy to work with.