CHHICHHORE is the story of 'loser' friends trying to become winners and learning some important lessons on the way. Annirudh Pathak aka Anni (Sushant Singh Rajput) is a middle-aged man residing in Mumbai with his son Raghav (Mohammad Samad) after divorcing his wife Maya (Shraddha Kapoor). Raghav is under immense pressure as he has just given the entrance exams for engineering. Both his parents were rankers when they gave the entrance examination.
As a result, Raghav is feeling the pressure tremendously. Anni however is confident that he'll make it. Finally, the result is out and sadly, Raghav fails to make the cut. Scared that he'll be labelled a loser all his life, he attempts to commit suicide by jumping from a high rise. He survives but the doctor treating him, Dr Kasbekar (Shishir Sharma) makes it clear that the chances of him recovering are slim. Anni is obviously heartbroken and with no option in hand, he decides to adopt a novel method to ensure that Raghav gets the will to live. He starts narrating him his story as an engineering student in Mumbai's National College of Technology. He's allotted a room in Hostel no 4 aka H4, considered to be the residence of the 'Losers'.
At first, Anni is flabbergasted with the kind of characters in H4. But slowly, he becomes good friends with some of them like Gurmeet Singh Dhillon aka Sexa (Varun Sharma), Acid (Navin Polishetty), Sundar aka Mummy (Tushar Pandey), Bevda (Saharsh Kumar Shukla) and Derek (Tahir Raj Bhasin). The number of girls in engineering is negligible and the most popular among them is Maya (Shraddha Kapoor). Anni manages to woo her and they soon start dating. However, Anni and others are still called 'Losers' and there's a reason for it. The General Championship aka GC is a sports tournament that takes place annually in the college. The students of H4 always lose miserably and are the last among the ten hostels.
Hence, the 'Loser' tag. Raggie (Prateik Babbar) from H3 is a champion who wants all the winning students from other hostels to be in his hostel so that H3 can win the GC. He invites Anni, since the latter is a basketball champion. But Anni refuses, thereby earning the wrath of Raggie. Anni and others from H4 decide to shed the tag of 'Loser' once and for all by winning the H4. However, the road to the trophy is full of hurdles. Cut to present-day. Raghav's condition stops deteriorating after listening to the story of the 'Losers' but there's no improvement either. What happens next, in the flashback as well as in the present day, forms the rest of the film.