Well, here's a video from last fall taken
just outside that Home Depot. I'm 5'4" HWP female and I would never walk alone around Halsted and Belmont at 1 am (or 10 pm or anytime after dark), let alone walk all the way to the Home Depot parking lot. I used to live a mile from the very blocks you're referring to, and now I live 2 miles from there. I know this neighborhood like the back of my hand, and have lived here for 25 years, so trust me when I tell you that I know what I'm talking about.
You've said you live in a small town, so let me be blunt: You are asking for trouble if you chose to walk in the neighborhood late at night. You're asking for trouble if you choose to wait at a bus stop. Plenty of people in groups of 2, 3, 4, 5 people still managed to get mugged on a weekly basis. A guy got murdered for his cell phone last year. Skim through the reports on
Crime in Wrigleyville and Boystown. Read the
second paragraph of this article and know that it's referring to the very street you're considering walking down to get to the Belmont L Station and Home Depot.
Going to the Boystown bars is fine, but you absolutely must cab/Uber there and back. Don't be pennywise and pound foolish, just absorb the cost and realize it's the price to pay for going out in the city.