Fly nonstop from New York-LGA to Chicago-MDW for $102 roundtrip this winter on Southwest.
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.