Where can I buy a Strawberry tree surrounded by Chicago or the Mid-West? ...

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Answers:    Strawberries don't grow on trees they are plants.
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Strawberries grow on plants, and Chicago is in the midwest, and yes you can grow and buy strawberry plants surrounded by the midwest. They are out of season right now though, individual that it is winter there. If you are surrounded by Chicago (the midwest) I am surprised that you do not know this. Locate a hardware store, or a gardening store, you can go to the rack of seed, pick out the seeds, and after you can grow your own plants in the spring. I suggest it will take 2 or 3 years previously you will get strawberries tp pick though, and you will stipulation a couple packs of seed so you can plant enough to capture pollinated.
Good luck, and send some this instrument ;o)