Flights at this price are valid on Tuesdays and Wednesdays with the odd Sunday or other weekday mixed in randomly. Other travel days are available for $56 one-way, so you can mix and match and still come up with a cheap fare so long as you depart midweek. Seats are wide-open from late January through mid-March at this price point.
The only place you can purchase Southwest flights is on their own website, where I found seats departing LGA on Wednesday, February 13 and returning from MDW on Sunday, February 17, 2019. Perfect for a surprise Valentine's Day getaway with a loved one.
Are you following our dedicated NYC deal feed on twitter yet? If not, be sure to add @awddeaksnyc pronto and never miss out on an airfare deal again.
Looking for a lovely place to stay in Chicago over that Valentine weekend? Here's what we choo-choo-choose for you on those dates via Hotelwatchdog.