For travel over President's Day weekend, fly nonstop from New York to Chicago for $260 roundtrip on American.
Searching AA.com, we found seats departing LGA on Friday, February 15, returning from ORD on Monday, February 18.
You'll find slightly lower fares available for travel in basic economy, which won't include seat selection and other perks. Also keep in mind that this itinerary falls over what is a three day weekend for many, so fares are a tad higher than they will be for later in winter.
See our New York LGA fare listings for a complete look at current finds.
Need a room in Chicago? Here's what's available on Hotelwatchdog for these dates.