Love of my life- Chicago

I love the city of Chicago. It is my all time favorite city in the US which may not make sense to some. It's not the warmest, it's not on the coast, it doesn't have trendy people. Ok actual Chicagoans may balk at that as they consider themselves very trendy. Being in the midwest adds up to very nice people compared to the coasts. The city is beautiful in the winter when all the holiday lights are in place but also in the summer when the beach is in full swing and Michigan Avenue and Navy Pier are packed with tourists.
And of course fantastic shopping, restaurants, art and culture. I can not understand why Chicago is not everyone's favorite city. Despite my naked adoration, I have a confession to make. I don't like the cold weather so I don't visit Chicago between the months of November and March if I can help it.
Similarly, I love London and Paris and would never turn down an opportunity to visit those cities but I would really think twice before accepting a winter invitation. That's how sensitive I am to weather. Which brings me around to my question-- how great can a city be if you have to avoid it for a good portion of the year?