Since you live in Chicago, you should get proper real winter tires. Then keep the good summer tires and switch them in April and November. They are hard to find for the 19" wheels but they are out there and you have some leeway in sizes and speed rating -- they don't have to be exactly the same as the stock tires. I went 10mm wider all round but was able to find the very good michelin Pilot Alpins in XL load rating and they fit just fine. Tesla has other winter tires specced for the 19" wheel that are also 10mm wider so I knew they would fit just fine.
e.g., Simpletires right now has the X-ice for the front and Pilot Alpins for the rear. Not matching is ok, but if you look around you can probably find a matching staggered set. look at Tirerack, simpletires, 1010tires and call local tire places who can usually order from those and other places. Look at the Tesla parts catalog for the full range of sizes that fit on the OEM wheels. Also see the tire thread here that has those sizes listed and a good discussion.
Thread for useful information and informative discussion of tires and wheels for the 2021.5 refreshed Model S. The OEM wheel options for LR and Plaid are: 2 WHEEL, 21X10.5J, ARACHNID, REAR 1234229-00-C Over-the-Counter(No VIN) $1,210.00 2 2 2 WHEEL, 21X9.5J, ARACHNID, FRONT...
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