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Welcome to Chicago the largest community of any Midwestern city. There a few neighborhoods where Jewish life thrives. Lots of shuls, kosher restaurants and supermarkets to choose from. Chesed LAvrohom, R' Yehoshua Eichenstein, has almost around the clock minyanim. Some of the larger Yiddish neighborhoods are at Skokie, Paterson Park, West rogers Park
West Rogers Park
At the intersection of Devon st. and California one of the most Jewish neighborhoods. Even the street signs are Jewish. Bordering the edge of Evanston, it is the home of the Chicago community Kollel.
Skokie a northern suburb, it gained national fame in 1978 when a nazi group gained permission to march through a neighborhood of Holocaust survivors. Plenty of Jewish life especially on Dempster St. where there are plenty of jewish stores. A Holocaust memorial can be found here.
For information about the eruv, mikvaos and much more be sure to check the crc guide to visitors
KEY SHUL'S \ MINYAN FACTORIES
The main Hashgacha is the Chicago Rabbinical Council (CRC) http://www.crcweb.org/