Get round-trip flights on Southwest Airlines with rates from $98 on Airfarewatchdog. We found the lowest fares on flights between Chicago and Cincinnati starting 6/6. Flights from Boston to Orlando start at $148, and flights from New York to Minneapolis start at $144. You can enter your own travel dates and locations to find fare prices on Airfarewatchdog. Some of these flights need to be booked at least 21 days in advance and require travel on specific days of the week. Prefer to book a vacation package with the airline? There's a California promotion going on at Southwest Vacations, too. Taxes, fees, and restrictions may apply.