What's the cheapest month to fly from Chicago to NYC?

For this route, late January through March and again in November (skip Thanksgiving week) tend to be your cheapest windows to fly. Business and leisure demand both dip during these stretches, so airlines drop fares to keep planes full. Summer months and the December holiday season are the priciest times to book, thanks to heavy travel demand on both ends.If you're tracking flights from chicago to new york , try comparing a full month's fare calendar instead of locking into single dates — this route is flown so frequently that prices can shift noticeably even day to day within the same "cheap" month.