Maybe if you live in Manhattan. If you live out in Bayridge, you can get a 750+ sqft 1-bedroom apartment for $1450/mo. It takes me roughly 35 minutes getting to Soho on the R/N train from 86th st [which is near the end of the R train]
Pricing for housing is definitely cheaper in Chicago but the pay sucks. It's not uncommon for lead-engineers to make < 6-figures. Tech is definitely not a priority in that city which may or may not be a bad thing.