The story begins in the St. Petersburg law courts, where three friends and colleagues of a man named Ivan Ilych learn from the newspaper that Ivan has died. No one seems deeply affected by this, but one of them, Peter Ivanovich, goes to the wake at Ivan's house that night out of a sense of obligation.
There Peter finds his friend Schwartz, who's eager to leave the dreary service and spend the evening doing something more fun: playing bridge. Peter Ivanovich also has a chat with Praskovya Fedorovna, Ivan's widow, who puts on a spectacular (but rather unconvincing) display of tears and then promptly asks Peter how she can milk Ivan's death for all the pension money it's worth. As for Peter himself, the death of somebody so similar to him makes him very nervous. After a valiant effort not to let Ivan's funeral service affect him in the slightest, he leaves in a hurry to get to the bridge game.
Now that the "prologue" is finished, the narrator gets down to the business of telling us Ivan's story. Ivan, who died at only forty-five, had a life that was "most simple and ordinary and therefore most terrible" (2.1).
The narrator then hurries us through Ivan's childhood and school days. Young Ivan is a likable fellow: smart, good-humored, well balanced, sociable, and witty. He has a few scandalous debauches, but not too many. After attending law school he slowly works his way up the career ladder as a legal official, moving from province to province every few years or so. In one of his provincial postings he meets a girl named Praskovya Fedorovna, whom he marries, though he doesn't really love her.
Ivan is fairly successful at work (enjoying the sense of power that legal work gives him), and popular socially. Initially his marriage is pleasant too, but when Praskovya Fedorovna becomes moody and difficult during her first pregnancy, Ivan can't deal with it. As a result he retreats into his work and his bridge games, which seem to be his real passion in life. His marriage never recovers, but Ivan doesn't really care about that. Despite his marriage, Ivan finds life to be quite pleasant. At least Praskovya Fedorovna provides him with a daughter (Lisa) and young son (Vasya).
At around age 40, Ivan is upset terribly when's he's passed up for an expected promotion. It's the worst thing that has ever happened to him. After a brief stint of depression, he heads to St. Petersburg alone to find a job with a better salary, and does. He also finds a new apartment, and a new passion for interior decorating; he'll make it the house of his dreams. But then, while working on the window drapes one day, Ivan falls from a ladder and bangs his side badly. He makes nothing of it, and even laughs it off, but after a while he starts to notice a persistent pain in his side and a bad taste in his mouth.
That decorating accident turns out to be a death sentence. Some time after Ivan's family comes to join him in St. Petersburg, the pain in his side starts to become more serious, and his mood takes a turn for the worse. He goes to see various doctors, but they give him different diagnoses and not one is willing to tell him whether or not his condition is serious. At first Ivan is hopeful that he'll recover and eagerly takes his pills, but nothing the doctors give him appears to have an effect. Slowly but steadily, he gets worse and worse.
Gradually Ivan comes to realize that he is actually going to die, but he can't quite wrap his mind around it. His fear, and the pain his illness brings upon him, make it impossible for him to enjoy work (or bridge, for that matter), and he finds that he can think of nothing but his own impending death. Eventually, he is forced by illness to stay at home and receive special care.
No one else around him – least of all his wife and daughter – seems to understand or care about what he is going through. They all go on with life as usual, and try to pretend his illness is just a passing thing. To Ivan, this seems totally "false," and he starts to hate all of them. Only Gerasim, one of the servants, is willing to acknowledge that Ivan is dying, and shows him genuine compassion. Ivan starts trying to spend as much time with Gerasim as he can.
One night, Ivan is particularly tormented. He can't bear to go on living as he is, but is terrified of dying. As he thinks over his life he is also startled to discover that almost no part of it was truly happy, except maybe his childhood. How could life be so senseless and awful? That's when it occurs to him that perhaps he's lived his life the wrong way. But Ivan can't believe that could be true – he thinks he's done everything right – and dismisses the idea.
As several weeks pass and Ivan grows nearer to death, he keeps returning to that thought, and keeps dismissing it. It's too painful to think it could be true. In the meantime, his physical pain grows increasingly worse. The combined mental and bodily agony becomes so horrific that for three days Ivan just screams and thrashes unceasingly.
On his very last day of life, Ivan is suddenly sees light all around him. This happens at the same moment when his son Vasya kisses his hand. His screaming and thrashing stop, and he accepts without resistance that his life has been a failure. But he also feels that he can still redeem it. Ivan opens his eyes and finds his family around him. For the first time he feels no hatred, but only sadness that he has made them suffer so much. He realizes that all he can do now to end their suffering, and his own, is to die. Suddenly his fear of death is completely gone. So, with joy, Ivan dies.