[02/13/2016 @ 1:26 PM] Fare has increased to $149, but expect it to drop back down in a few days. If you wanted it for $87, check back in a few days.
United and Southwest Airlines have round-trip flights from Houston (IAH / HOU) to Chicago (ORD / MDW) for $87-$122, NONSTOP. $44 to $62 each way. Cheapest flights midweek from February to May. Fare is reversible. Holiday blackouts apply.
No matter how old this deal is, you can probably find fares in this price-range midweek on most months up to 3 or 4 months away. We no longer send out regular notifications for this destination because it has been on sale since last year.