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Any Chicago owners with vintage detached garages? Question RE 220V

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I have a 115 year old house in Chicago with a detached garage that currently doesn't have 220V electrical service. The electrical meter is on the side of the house.

I got 3 estimates to bring 220V into my detached garage.

The first guy who seemed very knowledgable said he would have to pull a new line from the electrical box and string it overhead to a pole on the garage and then conduit into the garage for the 220V outlet. He seemed confident that pulling a permit wouldn't be an issue.

After that, I placed my order and sent it to production 4 gays ago.

In the mean time, I decided to get two more estimates. Both these guys (including Mr Electric, Tesla's recommended electrician in my area) were adamant that it can't be done without first having the power company install a second meter on the garage and getting a permit from the city will be problematic.

Just curious of anyone here has a similar setup and if they've run into any problems....
 
I had a somewhat similar issue in the suburbs of Chicago. I also have a detached garage and needed to run 240V to my garage (electrical meter on side of house as well); however, I already had 120V outlets in the garage, so there was existing underground conduit to the garage, and that existing underground conduit was large enough to handle the bigger wiring for the 240V outlet. The electrician did need to run the bigger wiring all the way from the breaker box (in my basement) to the garage, but there was no need for an additional meter at the garage.

I also received a quote from Mr. Electric, and they were by far the highest quote (simply because they wanted to start from scratch, dig a new trench, basically replace all conduit from breaker box to garage). All of that was not required to be code-compliant. In any case, I would not trust what Mr. Electric says you need to get done. Get a few more electrians out to give you options and better quotes.
 
I too am in the city and had an electrician run 220V to my detached garage. Even though my Model S has only a single charger I had him run 100 amp service because I also have a Nissan Leaf and want to charge both at the same time.

My garage already had 110V through conduit but it wasn't large enough for the cable he needed to run so he ended up trenching a new much larger conduit from the panel in the house back out to the garage and put a separate panel. From there he put each car's charger on a separate circuit.

Picture here: http://www.gagme.com/greg/tesla/slideshow.php?sect=pictures#tesla060313-03.jpg
 
I have a detached garage.

It cost us $2400 to upgrade the electric. That involved running a 40 foot conduit underground from our house and installing a 100 amp subpanel in our garage to supply the existing electric and the NEMA 14-50 plug I have. It was serendipitous for us since we were already digging up the backyard to install new pavers, so it was incorporated into the overall construction costs.

I haven't run into any problems yet. We don't have central AC, but we do have a few window units running during the daytime. I encountered one issue in the garage during this time when I was charging my car, running the shop vac and had spot lights on my car (was detailing late into the night) and ACs were running in the house. I had to disconnect the UMC for a while. So, it's continuous load. But, if you have an existing 200 amp service to your house, you probably won't have an issue.

(Our house is about 90 years old, but the garage is about 50 years old. The electric going to the house prior to this was literally an insulated wire that was buried; the guy digging the trench actually cut the line because it wasn't protected.)

See this thread.