Book round-trip airfare with prices from $117 during this sale from Delta Airlines. We found the best prices on flights from Chicago to Cincinnati. Flights from Chicago to New York start at $127, and flights from Boston to Orlando start at $145. Some of these flights require advanced booking and specific travel dates. For example, the Chicago to Cincinnati flight deals are for travel between June and November. Enter your travel information on AirfareWatchdog, then click "See All Details" next to your preferred flights to find out how to book them. Taxes, fees, and restrictions may apply.