The aerodynamic benefits of formation flight have been known for nearly a century. However, these benefits have yet to be realized in a commercial environment in part due to the hazards associated with close formation flight. This paper explores a more practical approach to formation flight called extended formation flight, which takes advantage of the persistence of cruise wakes and extends the streamwise spacing between the aircraft by at least ten spans. Induced drag savings are estimated in an incompressible analysis considering the effects of wake rollup, vortex decay, vortex instabilities, vortex motion, atmospheric turbulence and stratification, and stochastic behavior. Extended formations are found to be unpractical for streamwise spacings larger than about 50 spans between each aircraft. For spacings around 10 to 40 spans, with low to moderately-low atmospheric turbulence, a two aircraft formation has a maximum induced drag reduction of 30 ± 3%, while a three aircraft formation has a maximum induced drag reduction of 40 ± 6%. At these distances, aircraft tracking error is the most significant contribution to the variation in drag savings. Studies of transonic effects, ride quality concerns, and control and sensing strategies are necessary to further evaluate the potential of extended formation flight.