If You Won the Lotto Would You Stay in Chicago? (Lincoln: vacation home, to live in)

[Lucky Clover]

Originally Posted by ChiNaan

I'm not even sure I would stay in the U.S., let alone Chicago.

Same. I'd go explore the world, actually. With that kind of dough, I'd go visit any where there is to visit around the world.

[jtamay3]

I would move to LA before the check cleared.

[gomexico]

If You Won the Lotto Would You Stay in Chicago?

Yes. Why not?

[Vlajos]

I would stay, though I would buy a second home in Spain, Portugal, Italy or Greece.

[TBideon]

I'd probably wind up in Florence or Naples, though I'd buy a Chicago home for when I visit family in the US. Maybe something on Dearborn in the Gold Coast.

[chet everett]

Originally Posted by ChiNaan

I'm not even sure I would stay in the U.S., let alone Chicago.

I completely agree with the others that travel and / or having multiple residences is certainly feasible on a windfall of $100M or so and I tend to agree that Chicago does make a nice "base" for lots of people at a stage of their life where they want to have access to some of the wonderful amenities of the region -- if you enjoy professional sports it is great to be able to take in a playoff game with the Blackhawks, then see a a Sox game and maybe a Bulls game the same week. Despite the awkward exterior of the renovated Soldier Field it is a premier site for enjoying an NFL game. If more high brow / cultural offerings are also part of your tastes the access to CSO is uniquely close -- when the kids were little there were times when we would split up and part of family watched the Bears and part went to a CSO event. Similarly it is possible to stop in and visit the fine collections any of Chicago fine art museums. For folks that can afford a private school in Chicago or the determination to find a suitable public school in CPS or a desirable suburb it is hard to argue that your kids would get a better education elsewhere. And the food! While I am sure you can get fancier Chinese food in Hong Kong, better French food in Lyon, hotter Thai food in Bangkok, spicier Indian food in Mumbai and more elaborate Italian food in Florence I also know that having the variety and quality we have of each on every night of the week is pretty close to impossible, and none of em have a better beef sandwich!

The weather can be really grate on one's mood -- the rain and gloom of just a week or two ago would be signficantly less stressful if you knew you could hop on a plane and be in Miami or Marco Island or Palm Springs or Scottsdale or the Mediterranean... If / when things were looking up flying back to enjoy some seats in "the front row" of a sports / music venue would not be bad at all.

Of course having money in any city in the world does allow you to enjoy the best a place has to offer, and arguably if you are the kind of person that has a broad enough vision to put your money to work in ways that are uniquely available to those with an especially large pile of cash allows one to have signficant input in ways that "regular people" rarely do, especially in Illinois / Chicago -- folks have mentioned the role that the investor class of both right-leaning and left-leaning folks have here, from ensuring that legislation does not destroy our financial markets to helping speed along political agendas...

The weird thing is that one need only tune into the cable shows that show the "curse of the lotto millionaires" to give one second thoughts about doing anything other than remaining as hermit-like as possible. Of course I know many an entrepenuer that eventually had their fortune reduced by poor business decisions, an inability to control forces that reshape the economy and more than a little hubris -- you don't see cable shows about their "curse" becuase the fact is in the US it still just as easy to loose a fortune as anywhere on the planet...

[marothisu]

I forgot to add that I would donate a few million to charities for sure and be a partner in some sort of place that adds culture, and also a lounge. Then I'd lay low with the rest of it for awhile, earning interest off it before investing a little more in other things.

[mjtinmemphis]

I would probably have to research the tax laws for the state to see if that would be the smartest thing to do.

Off the top? No. Chicago is a great playground especially if one has money.

As with anything else, smart money decisions will go a long way.

[knitgirl]

10% of the gross to charity, a chunk to my sibs and parents. I would try to invest the rest pretty conservatively. I would definitely dump my place in Elgin, and buy something in the city, do a LOT of travelling.

[C. Maurio]

Originally Posted by Jesse69

If you won a $100 million cash value lotto, would you stay in Chicago or move to a better place? Where would you move too? If you stay how would you improve where you live?

Well, if I won, I'd remodel our back garage to be really long enough to enclose a 25' RV Trailer, with a garage opening height of 12 feet if that's good enough. I'd make it a little wider and I'd make it 2 story, the 2nd story to hold possessions like books and clothes. The garage would have a bay at the end for oil changes, too [already have this]. I'm already happy with my 3 story Wicker Park house, and it has a great location. But being rich I'd spend every winter in a nicer southern city, hence the RV. I've searched RV storage in the city and it hardly exists and if it does it's very expensive. Cheapest RV storage place also sells RVs and they have a 500 lot RV space storage, but the big problem is that they're 50 miles from Wicker Park past Aurora. So it sure would be nice to have an RV in you garage. Plus I can build my garage to be heated and insulated, so my RV wouldn't need winterizing.

I'd be tempted to get a 2nd house in the suburbs, but I need a place where you can park an RV in your driveway. Any suggestions for this? What suburb is great to live in with good food and shopping? The problem with suburbs are that the streets are not bike friendly, hence I still like Wicker Park.

When a building remodeler lived 2 houses away from me, I told him I dreamed of having a 2 story garage. He went through the permits and gov hassle and built a 2 story garage. But his house remodeling was a cheap disaster and had flaws and his house got foreclosed and was sold... Its only rented now as it's a hard to sell house.

When I lived in Houston I sure enjoyed the shopping and food there better, but the summer heat is killer. Getting a 2nd house there would be just too expensive, hence I'd rather rent our just live in an RV there for winter.

I would stay in Chicago for the months of May thru November. The rest of they year, Nevada, Florida or Arizona.