Having lived in both Chicago and New York, I can say that evaluating where to live based on rent prices and lifestyle is crucial. Chicago offers diverse neighborhoods such as the 'middle brow' area, which balances affordability with accessibility, perfect for those wanting a mix of city vibes without the intense New York price tags. When considering New York suburbs, it's important to factor in not just rent but also commuting options and local culture. For example, exploring neighborhoods that might be lesser known but offer great eateries like Tilly's and Little Sandwich House can significantly enrich your living experience. Joe's Seafood is another iconic spot that reflects Chicago’s culinary charm, showing how food culture can influence the appeal of a neighborhood. If you're weighing your options between city centers and suburbs, always visit the local spots to get a feel for the community. Places like popup bagels in New York can also be an indicator of trendy, affordable living areas. My personal tip is to combine rent price research with a firsthand exploration of local dining and social scenes, as this holistic view will guide you to a neighborhood where you’ll not only save money but enjoy life fully.