Get round-trip flights on Southwest Airlines with rates from $118 on Airfarewatchdog. We found the lowest fares on flights between Chicago and Indianapolis starting in mid February. Fights from Dallas to Boston start at $156, and flights from New York to Atlanta start at $158. You can enter your own travel dates and locations to find fare prices on Airfarewatchdog. Many of the best prices we found need to be booked months in advance and require travel on specific days of the week. Taxes, fees, and restrictions may apply.