Ivy won't survive Chicago winters in a pot — container plants experience 20°F colder temps than in-ground. Plus, ivy damages buildings with holdfasts that trap moisture against walls. Instead, install a large trellis and plant hops (Humulus lupulus) in a 24-inch+ pot — it's tough, fast-growing, and has decorative flowers. Or grow annual morning glories in sun (no fertilizer — they bloom best in poor soil).
For evergreen screening, consider a hardy vine in a very large insulated pot, but hops or morning glories are more reliable and beautiful.
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