Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago to Tupelo as you normally would.
For a flight from Chicago to Tupelo, you will be flying into Lemons Municipal. Tupelo Lemons Municipal (TUP) is just 3.6 mi from the center of the city. Lemons Municipal is the only Tupelo airport and it handles 0 inbound flights from Chicago per day. 0 airlines have flights to Tupelo Lemons Municipal from Chicago on a regular basis.