• Home
  • Latest
  • Fortune 500
  • Finance
  • Tech
  • Leadership
  • Lifestyle
  • Rankings
  • Multimedia
Big Data

Flight Canceled? How This App Can Book You a New One in Seconds.

By
Donna Fuscaldo
Donna Fuscaldo
Down Arrow Button Icon
By
Donna Fuscaldo
Donna Fuscaldo
Down Arrow Button Icon
April 21, 2016, 12:00 PM ET
Freebird app
Freebird appCourtesy of Freebird

Winter may be behind us but that doesn’t mean flight issues are going away. In the last thirty days, more than 9,000 domestic flights have been canceled and another 139,000 delayed. Travelers caught up in it know all too well the pain it can cause.

Cambridge, Mass.-based startup Freebird can’t prevent flights from being canceled, but it is aiming to alleviate the headache of finding a new one. Launched this past November, Freebird is an app-based service that tells travelers when their flight is disrupted, offers them alternative flights in less than 30 seconds and — perhaps most importantly — pays for their new ticket. The service, which differs from travel insurance, costs $19 for a one-way trip or $34 for round-trip and is only available for domestic travel.

It’s a risky undertaking for Freebird, but one the company says is made safer because of big data. Like an insurance company that bets nothing will happen more of the time, Freebird relies on algorithms and experienced travel data scientists to assess the risk it faces from flight delays and cancellations. In order to maintain its business, Freebird has to understand how airlines price tickets that are purchased on the same day. It also has to gauge cancellation rates across different airlines and routes.

“We’re looking at weather data, flight pricing and availability data to be able to compute prices correctly so people traveling can get where they need to go but we can still have a business,” says Ethan Bernstein, Freebird’s 31-year-old co-founder and former Expedia executive.

Unlike travel insurance, the service doesn’t place restrictions on the types of flight disruptions covered or reimburse travelers for their original flights. The idea, Bernstein says, is to solve a pain point in real time. Travelers can enroll in Freebird up until two days before their flight. When a flight is canceled or delayed for more than four hours due to weather, maintenance problems or any other issue, they get a text alerting them to the disruption followed shortly after by a link with a choice of alternative flights. The traveler gets to pick the best time for them irrespective of which airline the flight is on or how much it costs.

 

Freebird isn’t alone in coming up with new ways to help travelers get from point A to point B. There are a number of other data-driven mobile apps on the market that do everything track flights in real time to send out status alerts when disruptions happen. There’s even one that helps consumers get compensation for any delayed or cancelled flights that have occurred in the last three years.

Freebird co-founders Sam Zimmerman, left, and Ethan Bernstein, right.
Freebird

 

What backers of Freebird says sets it apart is the experience and knowledge Bernstein brings to the company after working at Expedia for four years. “One of the things we love to back is depth,” says Jeff Fagnan, founding partner of Accomplice, the early stage technology venture firm that participated in Freebird’s $3.5 million round of funding in November 2015. “Bernstein is living in the industry and working in the industry for a long time.”

Fagnan admits he didn’t intend to invest in the company, figuring it was just another play on travel insurance. But he was quickly impressed with Bernstein’s “knowledge and passion” and a lack of what he saw as clear competition. “We looked around and saw some other examples of different types of travel insurance. But it was more taking an old broken business model and redoing it in a digital format,” he says.

Related: 7 Airline Insider Tips That Will Make Flying Less Grueling

Freebird hasn’t had to spend money on marketing to date, growing in its short time thanks to word-of-mouth referrals and repeat business. It’s piquing the interest from airlines, the travel industry as well as credit cards companies and insurance providers.

“Our aspiration is to be a check-the-box everywhere airline tickets are sold,” Bernstein says. “Whether the ticket is sold by an online agent, corporate travel agent, airline or website we want customers to be able to say yes to have Freebird part of the purchase.”

Currently Freebird is going after the business travel market but says anyone who is time-sensitive would likely be willing to pay the extra money to know they will make it to their destination without a headache and added expense.

Still Julie Ask, an analyst at Forrester Research isn’t convinced everyone will want to check off Freebird as an added service. She says frequent business travelers can get a similar service from their airline while consumers may not think the service is necessary.

“The challenge is the vast majority of the revenue in the airline industry comes from frequent flyers and if my flight gets canceled United Airlines takes care of me,” she says. “If its targeting leisure travelers who might travel two or three times a year the cost may be too high for them.”

About the Author
By Donna Fuscaldo
See full bioRight Arrow Button Icon

Latest in

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025

Most Popular

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Rankings
  • 100 Best Companies
  • Fortune 500
  • Global 500
  • Fortune 500 Europe
  • Most Powerful Women
  • Future 50
  • World’s Most Admired Companies
  • See All Rankings
Sections
  • Finance
  • Leadership
  • Success
  • Tech
  • Asia
  • Europe
  • Environment
  • Fortune Crypto
  • Health
  • Retail
  • Lifestyle
  • Politics
  • Newsletters
  • Magazine
  • Features
  • Commentary
  • Mpw
  • CEO Initiative
  • Conferences
  • Personal Finance
  • Education
Customer Support
  • Frequently Asked Questions
  • Customer Service Portal
  • Privacy Policy
  • Terms Of Use
  • Single Issues For Purchase
  • International Print
Commercial Services
  • Advertising
  • Fortune Brand Studio
  • Fortune Analytics
  • Fortune Conferences
  • Business Development
About Us
  • About Us
  • Editorial Calendar
  • Press Center
  • Work At Fortune
  • Diversity And Inclusion
  • Terms And Conditions
  • Site Map
  • Facebook icon
  • Twitter icon
  • LinkedIn icon
  • Instagram icon
  • Pinterest icon

© 2026 Fortune Media IP Limited. All Rights Reserved. Use of this site constitutes acceptance of our Terms of Use and Privacy Policy | CA Notice at Collection and Privacy Notice | Do Not Sell/Share My Personal Information
FORTUNE is a trademark of Fortune Media IP Limited, registered in the U.S. and other countries. FORTUNE may receive compensation for some links to products and services on this website. Offers may be subject to change without notice.


Most Popular

placeholder alt text
Commentary
Yes, you're getting a bigger tax refund. Your kids won't thank you for the $3 trillion it's adding to the deficit
By Daniel BunnJanuary 26, 2026
2 days ago
placeholder alt text
Personal Finance
Current price of silver as of Tuesday, January 27, 2026
By Joseph HostetlerJanuary 27, 2026
1 day ago
placeholder alt text
Personal Finance
Current price of silver as of Monday, January 26, 2026
By Joseph HostetlerJanuary 26, 2026
2 days ago
placeholder alt text
Economy
An unusual Fed ‘rate check’ triggered a free fall in the U.S. dollar and investors are fleeing into gold
By Jim EdwardsJanuary 26, 2026
2 days ago
placeholder alt text
Success
As AI wipes out desk jobs, Citigroup CEO Jane Fraser says the company is training 175,000 employees to ‘reinvent themselves’ before their roles change forever
By Emma BurleighJanuary 27, 2026
1 day ago
placeholder alt text
Success
Despite running $75 billion automaker General Motors, CEO Mary Barra still responds to ‘every single letter’ she gets by hand
By Preston ForeJanuary 26, 2026
2 days ago

Latest in

C-SuiteCEO salaries and executive compensation
Here’s who topped the Fortune 500 in CEO pay last year—from Goldman’s David Solomon to Disney’s Bob Iger
By Marco Quiroz-GutierrezJanuary 28, 2026
12 minutes ago
Real EstateHousing
Trump now says he’s actually not ‘a huge fan’ of letting Americans tap their 401(k)s to use for a down payment
By Courtney Vinopal and HR BrewJanuary 28, 2026
35 minutes ago
people with masks over their faces sit cross-legged, crowded next to each other
CryptoCryptocurrency
Judge hits Chinese crypto scammer who helped swindle $37 million from U.S. victims with 46-month sentence
By Carlos GarciaJanuary 28, 2026
52 minutes ago
Personal FinanceCertificates of Deposit (CDs)
Best certificates of deposit (CDs) for January 2026
By Glen Luke FlanaganJanuary 28, 2026
58 minutes ago
Personal Financemortgages
Best mortgage lenders of January 2026
By Glen Luke FlanaganJanuary 28, 2026
1 hour ago
A drawing of a piggy bank on a rocket ship.
Personal FinanceSavings
Best high-yield savings accounts of January 2026
By Glen Luke FlanaganJanuary 28, 2026
1 hour ago