The London-based events start-up was acquired for £1.6M.
YPlan was founded in 2012, and has been backed by investors including Hollywood star Ashton Kutcher.
YPlan is an event ticketing start-up, which in the year to 2015 made a pre-tax loss of £6.2M.
The company has been struggling recently, and had been forced to let go almost a third of its workforce.
Time Out Group has stated that in acquiring YPlan, it hopes to accelerate and scale its ecommerce business.
Julio Bruno, chief executive of Time Out Group, said: "Developing e-commerce and monetising our audience is an important element of our ambitious growth strategy.
"We acquired YPlan because its advanced technology will significantly accelerate this strategy. It will enable us to offer our large audience more online booking opportunities, whilst improving the user experience.
"We look forward to welcoming the highly skilled YPlan employees to the Time Out team. Together we will be stronger than ever to bring our customers the capabilities to make the most of the city and to make Time Out an even better place to discover, book and share."
YPlan's founders Rytis Vitkauskas and Viktoras Jucikas said in a statement: "Today is an exciting day for YPlan as we become part of Time Out, a global media and entertainment company. Both companies are an excellent fit.
"For us as founders, the acquisition is a natural continuation of our vision for YPlan: to enable people to discover and do amazing things, whether in their beloved home cities or while traveling. We're both very proud to join with our team such an iconic brand and to be part of Time Out's next chapter."
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