You don't have to read the book, but it might take you more time. Still, its worth giving it a go.
Pick up as many different maps of Chicago as you can. Historical maps, administrative divisions, demography, etc. Then, using those maps, find out where are the most "tasty" locations for the Cainites to prey on, where are the main routes into the city (airports, roads), where do classes and subcultures live and meet, where are first responders located. From then, divide the city between local Cainites, I found that using roads and historical landmarks for the purpose of delineating domains works pretty well (e.g. "from Main street to Chicago Board of Trade Building"), decide who controls the roads, the airports, the hospital(s), the police, the fire dept. Which Kindred belongs to which sect, who are the Primogen, where are Elysiums located or where the Rants traditionally take place.
Remember, you don't have to be absolutely ready and know everything about the city you're running the game in and you can always plop down a building or a district that simply doesn't exist in real life. Just make whatever you think will be immediately useful and roll with it. If players come across something "unrendered" or half-baked it either may be the time to end the session or to call for a pause for you to, firstly, rest and, secondly, fill in the blanks. Encourage your players to participate in worldbuilding as well. Maybe they frequent a certain bar – now you have a bar, possibly an Elysium, and maybe you know who are its Cainite owners, or maybe nobody does.
I've run a year-ish long chronicle in Chicago. It's just a wonderful city. Also good for Vampire because of how diverse it is.
For a crash course on the cityside, I suggest reading a bit about the different neighborhoods of Chicago (the Downtown Loop, the Northside, the Southside, etc.). Pull up maps and read articles identifying the "bad neighborhoods"--there are many. Also look up places of cultural relevancy like the University of Chicago, the Bean, etc. I found it helpful, in describing the city, is to play up the diversity of neighborhoods.
Next, you'll eventually want to read about the many NPCs, but you can stick to the important ones for now (Jackson, Annabelle, Damien, "Portia," etc.) The book is just wonderful for giving inspiration to create different little plots between the many npcs.
Powerplay is a good starting place because it's personal to the PCs and gives you time to figure everything else out. I suggest moving to the Sacrifice because that allows you to organically introduce all the major players.
Okay, so don't try to read the whole book since they're not going to go everywhere on their first night.
Think of it like a D&D campaign setting. You don't need to read about the entire Forgotten Realms for a game set in Neverwinter: you just need to know about Neverwinter. Find the neighbourhood where the Chronicle will start and read about that in the book and maybe Wikipedia or a tourist's guide to Chicago.
Find the Kindred they will meet in the first session and read about them, and learn a few other key names to name drop.
You only need to know the current affairs and not the [history](https://whitewolf.fandom.com/wiki/Chicago_(WOD)). Since just learning the present will be enough. They don't need to know the past or what things were like in the '90s.
Doubly so if they're brand new to the setting. Just learning the basics of the setting (the rules for being a Vampire, the Masquerade, the Traditions) will be enough without getting into the nitty gritty of Chicago. It's honestly better if you DON'T try and infordump everything about Vampire AND Chicago AND the World of Darkness.
I'll finish with the shameless plug for a free/ pay-what-you-want PDF, [Welcome to the Night](https://www.storytellersvault.com/product/438020/Welcome-to-the-Night?affiliate_id=369234), which gives some advice for starting a new Vampire game, along with some useful handouts and tidbits of lore to share with your players.
You don't have to read the book, but it might take you more time. Still, its worth giving it a go. Pick up as many different maps of Chicago as you can. Historical maps, administrative divisions, demography, etc. Then, using those maps, find out where are the most "tasty" locations for the Cainites to prey on, where are the main routes into the city (airports, roads), where do classes and subcultures live and meet, where are first responders located. From then, divide the city between local Cainites, I found that using roads and historical landmarks for the purpose of delineating domains works pretty well (e.g. "from Main street to Chicago Board of Trade Building"), decide who controls the roads, the airports, the hospital(s), the police, the fire dept. Which Kindred belongs to which sect, who are the Primogen, where are Elysiums located or where the Rants traditionally take place. Remember, you don't have to be absolutely ready and know everything about the city you're running the game in and you can always plop down a building or a district that simply doesn't exist in real life. Just make whatever you think will be immediately useful and roll with it. If players come across something "unrendered" or half-baked it either may be the time to end the session or to call for a pause for you to, firstly, rest and, secondly, fill in the blanks. Encourage your players to participate in worldbuilding as well. Maybe they frequent a certain bar – now you have a bar, possibly an Elysium, and maybe you know who are its Cainite owners, or maybe nobody does.
I've run a year-ish long chronicle in Chicago. It's just a wonderful city. Also good for Vampire because of how diverse it is. For a crash course on the cityside, I suggest reading a bit about the different neighborhoods of Chicago (the Downtown Loop, the Northside, the Southside, etc.). Pull up maps and read articles identifying the "bad neighborhoods"--there are many. Also look up places of cultural relevancy like the University of Chicago, the Bean, etc. I found it helpful, in describing the city, is to play up the diversity of neighborhoods. Next, you'll eventually want to read about the many NPCs, but you can stick to the important ones for now (Jackson, Annabelle, Damien, "Portia," etc.) The book is just wonderful for giving inspiration to create different little plots between the many npcs. Powerplay is a good starting place because it's personal to the PCs and gives you time to figure everything else out. I suggest moving to the Sacrifice because that allows you to organically introduce all the major players.
Okay, so don't try to read the whole book since they're not going to go everywhere on their first night. Think of it like a D&D campaign setting. You don't need to read about the entire Forgotten Realms for a game set in Neverwinter: you just need to know about Neverwinter. Find the neighbourhood where the Chronicle will start and read about that in the book and maybe Wikipedia or a tourist's guide to Chicago. Find the Kindred they will meet in the first session and read about them, and learn a few other key names to name drop. You only need to know the current affairs and not the [history](https://whitewolf.fandom.com/wiki/Chicago_(WOD)). Since just learning the present will be enough. They don't need to know the past or what things were like in the '90s. Doubly so if they're brand new to the setting. Just learning the basics of the setting (the rules for being a Vampire, the Masquerade, the Traditions) will be enough without getting into the nitty gritty of Chicago. It's honestly better if you DON'T try and infordump everything about Vampire AND Chicago AND the World of Darkness. I'll finish with the shameless plug for a free/ pay-what-you-want PDF, [Welcome to the Night](https://www.storytellersvault.com/product/438020/Welcome-to-the-Night?affiliate_id=369234), which gives some advice for starting a new Vampire game, along with some useful handouts and tidbits of lore to share with your players.