With a service area that covered a majority of the southeastern US, the company operated an average of 5000 flights annually.

[2] ImagineAir was often noted for its young management; as founders Aaron Sohacki and Benjamin Hamilton were 19 and 21 respectively when the company was founded,[3] as well as its innovative online aircraft booking system, providing the familiarity of buying an airline seat on a charter.

[4] ImagineAir's business model was based on an industry study of the Small Aircraft Transportation System (SATS), developed by NASA.

[3][9] In March 2014, ImagineAir announced a merger with the Danbury, Connecticut-based operator Kavoo in an effort to become the first nationwide air taxi carrier.

The merger widened ImagineAir's service area to include the entire east coast of the United States and created the largest part 135 air carrier by flight volume.