City Cast Chicago logo

Book Report: ‘Olga Dies Dreaming’

Posted on November 20, 2025
Emily Mack

Emily Mack

Book club

Our monthly-ish book club, graciously hosted at the American Legion in Evanston. (Courtesy of Kathy Pierce)

Let’s get something out of the way immediately: “Olga Dies Dreaming” is set in Brooklyn … Still, there’s lots for Chicagoans to love in this far-reaching tale about gentrification, family trauma, and Puerto Rican identity.

Perhaps that’s why the Chicago Public Library picked “Olga Dies Dreaming” for One Book, One Chicago. The program aims to get Chicagoans on the same page — literally — and culminates tonight with author Xochitl Gonzalez at Harold Washington Library.

My own book club took part in One Book, One Chicago, and today I’m proud to present Hey Chicago’s first-ever book report.

What Is ‘Olga Dies Dreaming’ About?

The year is 2017, and Olga Acevedo is one of New York City’s most sought-after wedding planners. She’s hot, tough-as-nails, and caters to the elite with relatable cynicism.

Her brother Prieto is also hyper-successful: a congressman who runs on a common-man image, though he’s got skeletons in his political closet ...

Both siblings’ careers are a far cry from their troubled upbringing in Sunset Park. Their parents were former Young Lords, with their mother eventually leaving to pursue revolution in her ancestral home, Puerto Rico.

When Hurricane Maria hits there, both siblings confront their connection to her — and to Puerto Rico. Also, Olga learns to let her guard down for love. (Of course.)

Key Themes

Not everyone walks around constantly weighing their obligation to dismantle colonialism. But, informed by their mother’s leftist politics, Olga and Prieto do. The result is a lot of guilt, particularly for Olga, who opts for her own glitzy American Dream. At least at first.

🚨 Spoiler alert: She amends that dream for a humbler life in Sunset Park, where her manic pixie landlord-boyfriend curbs gentrification.

Meanwhile, Puerto Rico undergoes its own changes in the aftermath of Hurricane Maria. “Olga Dies Dreaming” acutely presents not only the physical devastation, but the federal government’s failure to help and corporate interests vying for land.

The Chicago Connection

The most direct reference to Chicago in “Olga Dies Dreaming” is the Acevedo parents’ history as Young Lords. The far-left activist group arose from a Puerto Rican street gang in Lincoln Park in 1959.

Led by José “Cha Cha” Jiménez, the Young Lords allied with Black Panthers to fight Mayor Richard J. Daley’s racist vision for urban renewal, staging occupations, sit-ins, and garbage-dumping protests. The Young Lords eventually expanded to East Harlem in 1969.

“Olga Dies Dreaming” also maintains a spiritual through line to Chicago, I think, as the characters reflect on the transformation of their own beloved neighborhood.

Similar Titles

“Olga Dies Dreaming” pays loving homage to Brooklyn’s Sunset Park. Set in Chicago, these fiction and non-fiction titles paint similarly detailed neighborhood portraits:

Share article

Hey Chicago

Stay connected to City Cast Chicago and get ready to join the local conversation.

Can't subscribe? Turn off your ad blocker and try again.

The latest in Chicago

Chicago, ExplainedAugust 28

Take This Week's Chicago News Trivia Quiz

How closely were you paying attention to this week's current events in Chicago? Test yourself in our weekly trivia quiz.

An older photo of Dolly Parton singing into a mic with a purple background
Keep It LocalAugust 27

How To Start Growing Your Own Food

Amid a summer of foodborne illnesses, intense weather, and ever-rising grocery prices, many Chicagoans are exploring ways to grow their o...

A man in a bucket hat and glasses holding vegetables in a large garden
Keep It LocalAugust 27

Your Guide To Chicago’s Garden Shops

From expansive gardening centers to little shops packed with houseplants, it’s not hard to find all the supplies you need to bring some m...

A garden with an assortment of big leafed plants
Keep It LocalAugust 20

How Transit Tees Turns Chicago’s Quirks Into Board Games

From board games about the city’s history to puzzles of iconic maps to card decks featuring local wildlife, Transit Tees’ teams of creato...

A person writing on a gridded paper that says "Chicago 1893" There's also a board game with an assortment of different houses for the board game on it. There is also A bowl of popcorn and a soda on the table
Keep It LocalAugust 20

Your Guide to Chicago’s Toy Stores

From vintage toys to a workshop series for aspiring toy inventors, Here's a list of places that’ll help you spoil the kids in your life a...

A table with an assortment of different stuffed animals
Keep It LocalAugust 13

Your Guide to Chicago’s Stationery Stores

Whether you’re actually going back to school soon or you just love analog hobbies, these local shops will help you find all kinds of stat...

A large group of people inside a store. They are looking at an assortment of items
Food & DrinkAugust 13

5 New Spots to Dine and Drink

Chicago is hot AF right now — and so is the dining scene. These recent openings have caught our eye.

A room with velvet drapes on every wall. On the ceiling there are chandeliers and people are sitting at a booth
Keep It LocalAugust 13

Family-Run Atlas Stationers Has Supplied Chicago’s Pens For Decades

For decades, the family-run shop delivered office supplies in bulk to offices in the Loop.

The outside of a brick building, the sign says "Atlas Stationers Inc"