Chicago
Departing City: New York
Hotwire Price: $72.30
Speaking of free, back-to-nature experiences, it’s hard to beat the Lincoln Park Zoo or the Cloud Gate in Millennium Park, especially if you’re traveling with kids.
On the grown-up side of things, you’ll have plenty to spare for $10 to $15 tickets to the late February Pancakes and Booze Art Show at Reggie’s on State Street since the Hotwire flight runs less than $75.
