Relocating to Chicago, IL from Cupertino, CA

Asked by Theinternet, San Jose, CA Mon Oct 3, 2011

Is it worth the move? We want to move out because of the cost of living in Cupertino. But the schools and weather are perfect. How is Chicago in terms of schools, weather, cost and real estate? Is it a good place to raise family?

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Alan May, Agent, Evanston, IL
Tue Oct 4, 2011
I've been to Chicago... oh, wait... I'm IN the Chicago area.. and have lived here for more than 40 years.

The business climate in the greater Chicago area is second to none. We have culture, museums, theatre, restaurants, transportation, and multiple sports teams and arenas. We have a world-class international airport, and Lake Michigan for sport, relaxation and fun. We've got the cubs, sox, bears, blackhawks, wolves... and more.

We have a prime location, central to many things, nationally high ranking schools, and universities and much, much more than I can mention here.

Weather? well, there's an old Chicago saying. If you don't like the weather, here in Chicago... wait a few minutes, it'll change. If we had the weather of, let's say, a "San Diego".... nobody would ever leave Chicago... so it would be unfair to the rest of the country. But we have everything else.

Does it get humid here in the summer? Are the winters unbearably cold and long? Yes. Would I live anywhere else? Well, maybe... San Diego sounds nice, and Paris is nice in the spring... but Chicago is a great town.
1 vote
Michael Cheng, Agent, San Jose, CA
Tue Oct 4, 2011
I've been to Chicago during its much hyped summer season, and even with the weather composed at its most pleasant manners, I could hardly wait to get back to San Jose and the Bay Area. I've travelled to other parts of the country and have found nothing quite comparable, except for San Diego as Shelley very correctly pointed out. Maybe I'm not just getting the point of the Mid-West summer humidity or freak thunderstorms. And, my cousins who've been in the Chicago area for grad school cannot be more eager to return to their LA home. For them, the infamously blustery and long Chicago winter is the deal breaker.

Chicago has a very wide range of schools, neighborhoods, and real estate prices. For a comparable neighborhood to Cupertino, you'd have to pay about 60-80% of the price for an equivalent home. And there are definitely some fantastic schools as I drove past a private high school that verged on Gatsby-like ideals, where lush, rolling lawns anchored by stately trees securely enrobed a brick cathedral of learning. For the well-heeled, life is definitely good with world-class restaurants serving up epicurean delights and a plethora of culturally-stimulating events. Our current President and family are as good an example as any that you can live and do quite well in Chicago.

For you, I suppose the only real question is whether you think all the effortlessly amazing sunny days spent outdoors around the Bay Area is worth the expense. Then again, you only live once.
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Shelley Linde, Agent, Rancho Santa Fe, CA
Mon Oct 3, 2011
Unless you have a great career to look forward to in Chicago why go? I am a native of the Bay Area and I relocated to San Diego...for the weather, wonderful selection of homes and MUCH better schools. I firmly believe SD is a wonderful place to raise children. San Diego provides outdoor activities that you can't get elsewhere due to the gorgeous weather. Swimming, horseback riding, biking, you name it. A much better
option for a kid than hanging out at the mall!

Contact me if you ever decide to make the move South!
0 votes
Chicago weather will age you quicker. California weather is kinder and you will look better longer.
Flag Fri Nov 8, 2013
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