Windy City (GTA 5 Chicago) is a map modification developed by Dekurwinator, FV Mods, Jdmimport and Lozano 71.  

Mod installation is placed in folders named after file address locations where you're meant to add or replace the included data, e.g. "mods-update-update.rpf-common-data" folder contains the file dlclist.xml which you are meant to add and replace at this location in your game: mods/update/update.rpf/common/data

If folder name ends with name.rpf/ you are meant to navigate to name.rpf file package in your game mods folder and then insert and replace any and all files as necessary.

You shall use a RPF editor tool such as OpenIV or CodeWalker to perform the installation process.

STORY MODE version

It's suggested to install the following mods, specially if your game is crashing or you are having difficulties after installing Windy City:

1. Gameconfig (latest), F7YO - https://www.gta5-mods.com/misc/gta-5-gameconfig-300-cars
2. HeapAdjuster, Dilapidated - https://www.gta5-mods.com/tools/heapadjuster
3. Packfile Limit Adjuster, Unknown Modder - https://www.gta5-mods.com/tools/packfile-limit-adjuster
4. No Boundary Limits, Unknown Modder - https://www.gta5-mods.com/scripts/no-boundary-limits-unknown-modder
5. Simple Trainer for GTA V (to teleport or noclip to map), sjaak327 - https://www.gta5-mods.com/scripts/simple-trainer-for-gtav

Find the map at these coordinates (you can copy the teleport lines over to Simple Trainer and teleport there directly by using the menu ingame):

WINDY CITY
[Teleport1Slot2]
x=3989.38
y=7070.4
z=15.00
MenuDescription=Windy City

NOTE: if you want to remove low detail city surroundings (blurry textures, low quality models), use OpenIV or CodeWalker to open dlc.rpf located in: "mods/update/x64/dlcpacks/rmp_chicago/" and replace the 2 files (content.xml, setup2.xml) with the existing files.

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Legal: All content belongs to Codemasters, Rockstar Games and Take-Two Interactive.
Codemasters
https://www.codemasters.com/
Rockstar Games
https://www.rockstargames.com/
Take-Two Interactive
https://www.take2games.com/

GTA 5 Chicago, Windy City, Windy City Christmas Edition use a base map mod for GTA 5 called Race Map Pack by Dekurwinator. https://www.nexusmods.com/gta5/mods/169?tab=docs