Chicago

Greystone two-flats, brick bungalows and vintage courtyard buildings fill the neighbourhoods, with high-rises along the lake. The Loop is the commercial centre, and 77 neighbourhoods each have their own character.

The L train system, Metra commuter rail and buses make car-free living possible in many areas. Lake Shore Drive and the expressways are the main driving routes.

In 2026 the median sale price is about $365K, roughly $4,300 per square metre, and a typical 2-bedroom rental costs about $2,500 a month. Prices are up 4.2% on a year ago and homes take around 40 days to sell, which points to strong demand.

Illinois property taxes are among the highest in the US and should be part of any budget. Winters are cold, so heating costs and building age matter.