Little Amiran is getting decked by her mother in gold & flowers on her engagement day . When he mounts his horse , she asks her father to get her oranges & dolls , amusing her mother .
While Amiran's father is away , she's abducted by Dilawar, who has just completed a 12 year stint in prison , thanks to Amiran's ' daroga ' father . In a desolate place , she's locked up with Ramdei - another tearful little girl , abducted from a fair . The two children embrace each other in the dark and cry for their families .
Soon a buyer arrives - a representative of a local begum who purchases Amiran to be part of her household . In the last moment the broker changes her mind & takes Ramdei since the begum had specified a fair girl & Amiran was dusky .
That leaves Amiran by default to the only other buyer - Khanum Jaan , the madam of a luxurious establishment catering to the wealthy louches of Lucknow in 1840 , British India .
Amiran is ushered into a vast courtyard to be presented to a bejewelled , hookah - smoking , brocade - swathed , reclining Khanum & sold . Khanum flanked by her lieutenant , Husseini ( a retired courtesan ) & protege Bismillah renames Amiran , Umrao .
Khanum casually claims her innocence in the child-trafficking by snorting in derision at the kidnappers , commenting to Husseini that she had no idea where the little girls were procured from & that if it wasn't at her establishment - the traffickers would've sold Amiran at another , anyway . Husseini agrees & adds that Amiran would grow under Khanum in luxury .
Neither Khanum nor Husseini hypocrtically act on Amiran's claims that she was kidnapped from Faisabad & that her father is a ' Daroga ' there . ( To show their true colours , Amiran receives a beating from Khanum when she attempts an escape in the middle of the night )
Umrao tries to forget her life as Amiran & Faisabad & embraces her gilded cage , losing herself in expensive classical music & dance training with Bismillah . She leaves behind her oranges & dolls , & instead grows up being decked in jewellery & expensive fabrics in Khanum's opulent mansion , surrounded by persian carpets , marble columns , musical instruments & luxury . She channels her melancholy by showing a flair for composing ' shayari ' & learns under Maulvi , Husseini's paramour - an aging , sedate man .
A grown up Umrao quickly attains fame as an accomplished courtesan with her fine dancing , melodious singing & her mellifluous ghazals attracting well-heeled , aristocratic black-sheep from all over Lucknow , including the affluent Nawab Sultan , a bachelor .
Her illicit , poetry-infused romance with with Nawab Sultan ( a paying customer ) was idyllic ( including when Nawab Sultan confided to her that he was being pressurized to marry ) . Umrao advices him to obey his mother ( getting upset only when he tells her that he can't be her patron once he marries ).
Just like Umrao , Bismillah also favours one of her patrons more than the others & carries out a pointless romance with that aristocrat . When Khanum Jaan after being paid off by the aristocrat's mother , gets rid of him , Bismillah , in the light of her doomed romance , loses her loyalty to Khanum .
When Khanum Jaan's entourage goes for a picnic in the countryside , Bismillah is carried off by dacoits . The entourage is devastated at the horrors that Bismillah maybe subjected too & are paralyzed that they don't even have a body to bury .
Later , a wealthy , dark stranger arrives at the mansion in pursuit of Umrao . Faiz Ali quickly becomes Umrao's confidant with his warmth & genuine interest in her .
He gets concerned after he secretly witnesses Umrao illogically ripping up Nawab Sultan's robes when he announces his wedding . Faiz's heart bleeds for Umrao & he offers to take Umrao away to his estate to divert her from her melancholy . Umrao asks Faiz Ali to make arrangements with Khanum - to which he readily agrees & leaves .
After her showdown with Nawab Sultan , Umrao is desolate & withdrawn . Khanum gets a contract for Umrao to perform a ' mujra ' at an event in Sitapur . Umrao in her depression refuses to perform . This is when an outwardly motherly Husseini gets rough & dictates that Umrao has no choice .
After many years of living with Khanum's household , Umrao thought of them as family , forgetting her childhood trauma , singing & dancing willingly .
Now Umrao could see again that she was part of the ' family ' only because she was their cash cow who was being ' lovingly ' exploited all these years . They were her ' family ' only as long as she brought in the cash to maintain their lavish lifestyles .
This realization makes Umrao take drastic measures . The next time the gallant Faiz Ali rides into town , Umrao doesn't ask him to leave a deposit with Khanum , like she did on his last visit ; she instead elopes with Faiz , who obliges by helping her up on his horse .
Unknown to Umrao , Faiz is a wanted man who gets hunted down by the soldiers of a local ruler . He's shot dead in front of her . Umrao is captured by the soldiers & interrogated by the ruler .
He lets go of her when he finds out that she used to be Bismillah's companion . Umrao is surprised to find that Bismillah instead of being dead or worse , had gotten a new lease of life & was thriving as the ruler's wife ( after his soldiers captured the dacoits who'd kidnapped her )
Though she was pleased to see Umrao - she was clear that she wanted nothing to do with Khanum or her entourage & wouldn't inform them that she was alive .
Umrao also longs to get away from Khanum ; Bismillah sets her up in Kanpur . Inspite of losing Faiz , Umrao bravely starts a new life alone where she freelances as a ghazal singer , barely surviving .
She accepts an invitation to sing at a little boys party , when the mother recognizes Umrao as Amiran . It was Ramdei .
After seeing Bismillah's horror turned to redemption , Umrao marvels sadly at how a last minute change in the sale made Ramdei the daughter-in-law of respectable people while Umrao fell into Khanum's hands .
To make matters worse , she discovers that Ramdei is Nawab Sultan's wife & was originally purchased as a companion by his mother. The begum , to subvert Nawab Sultan's estranged father's efforts to marry him off to his niece had got him married to her trusted Ramdei , who grew up in her care .
Though all three girls started from the same unlucky circumstances - Ramdei & Bismillah were miraculously delivered from their bleak destinies , while Umrao's last effort to restart life as Amiran , had failed with Faiz's death .
Husseini & Gauhar find Umrao in Kanpur & plead with her to return , claiming Khanum's ill health . Umrao returns to Lucknow to find Khanum looking well & realizes she was duped by Husseini & Gauhar - at that point Umrao declares her intent to return to Kanpur . Khanum feigns a casual reaction & asks Umrao to stay over for the festival before returning to Kanpur .
While Umrao is out of ear-shot , Khanum chillingly says that it didn't look like Umrao would stay with them willingly anymore & that other measures needed to be taken to restrain Umrao . They accomplish that with a false certificate of marriage between Umrao & Gauhar . Umrao is trapped . All of Khanum's machinations come to an end when the 1857 rebellion breaks out & they have to flee the city en-masse .
Umrao just walks away from the camp one night while the others are asleep . Maulvi sees her leaving & says nothing out of love for Umrao .
She returns to her place in Kanpur & restarts freelancing , but doesn't make much money with plain ghazal singing ( without lucrative ' mujras ' )
When she does finally get a gig for a ' mujra ' , she recognizes her old neighbourhood from her childhood days as Amiran . Full of hope , Umrao locates her family home & finds her tearful old mother who hugs her . Her father is no more .
The reunion is cut short when Umrao's brother refuses to acknowledge Amiran , instead telling his mother that she's ' Umrao Jaan - a famous courtesan from Lucknow ' . He implies that Amiran should've drowned herself than submit to her profession . Umrao runs away in tears . Her wailing mother is stopped by her brother .
Umrao has failed a fourth time at finding a place for herself in the outside world after her failure at trying to escape Khanum's mansion as a child , her doomed romance with Nawab Sultan , her elopement with Faiz Ali & finally her rejection by her brother .
Realizing that there was no place in the world for Amiran - she returns to Khanum's mansion in Lucknow & finds it looted & empty , symbolic of Umrao being emptied of hope at redeeming herself .