CheapAir.com was founded in 1989 by Jeff Klee out of his University of Michigan dorm room. Originally called 1-800-Cheap-Air, it started as a phone service for booking discounted air travel. In 1993, Craig Fichtelberg joined as a co-founder and president and began expanding the company nationwide from its base in California to cities like Chicago and NYC.
In 2000, CheapAir.com launched as a website to allow online booking. In 2011, they introduced a program called Price Drop Payback that guarantees to reimburse customers the difference if flight prices drop after booking.
In 2012, in response to airlines charging extra fees for amenities, CheapAir.com added the ability to book ancillary services like WiFi, in-flight entertainment, power ports, etc., during ticket purchase directly. Also, in 2012, they launched a new search feature called “Easy Search” that allows users to search for deals by entering natural language questions.
In March 2013, CheapAir.com created one of the first-ever iOS apps with voice-activated flight search, which went on to win a Travel Weekly award as one of the best travel apps. In November 2013, they became the first travel agency worldwide to accept Bitcoin as a payment option for flights.
In February 2014, CheapAir expanded bitcoin payments to cover hotel bookings, again being the first travel agency to do so globally. In February 2015, they booked the first direct flights from the US to Cuba after travel restrictions were eased.
In July 2016, CheapAir.com launched a monthly payment option through Affirm, allowing customers to “Travel Now & Pay Later” when booking flights and hotels. Most recently, in October 2022, CheapAir.com introduced a new “Green Choice” feature that highlights more sustainable flight options, moving towards more eco-friendly practices.
