I live in a 2 bedroom (2nd bedroom more of a small office, can’t fit a queen bed) in a high rise that is $4300/month. I have several friends on the Upper East Side of Manhattan, which I’d say is a pretty similar neighborhood to mine, paying ~$3500 for spacious 1 bedrooms in similar doorman/amenity buildings. It’s not that far off, only major difference is in unit laundry. River north/west loop/Gold Coast have plenty of 1 bedroom units in high rises in the $3k range. If taxes are literally equal in both cities, having a little more room in your apartment won’t be enough of a selling point, especially since Chicago is much more of a car city which is an added cost for most.