re: Chicago CTA Trains?

I was there as a tourist a few years ago. Got a pass for train/bus and hit the road. Used the trains/buses every day for a week. No further south on red than Chinatown, and north to Addison for Wrigley. Went to the end of green (plus walk/Lyft) to visit the Frank Loyd Wright house and Johnnie's Beef. All over the interior areas. Never had a problem, but I was on alert in some of the stations at night when few people were around.

The Architecture Center had a "Neighborhoods" open-top bus tour at the time that was a great way to explore the various ethnic neighborhoods in a short time. You'd run yourself ragged trying to visit all the places it covered in 90 minutes or so. Well worth it if you can find something similar.

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Regarding the Red line north, I think it ends at Howard, then the Purple extends into Evanston?

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Correct, but the Purple Line does run to/from The Loop M-F during peak hours.

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I'll probably avoid Red past Chinatown and the Forest Park blue line looks pretty sketchy between UIC and Oak Park as the CTA goes through some really rough neighborhoods.

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Few thoughts here:

- While I think it's OK to avoid the Red Line going south past Chinatown and Sox-35th, I wouldn't discourage you from avoiding the south side in its entirety. Take ME from Millennium Station and explore Hyde Park, for example. Museum of Science & Industry is right there and Jackson Park is a great walk. Also, one of the best restaurants in the city, Virtue, is right in Hyde Park, too.

- If you do end up in Chinatown, make it a point to swing into Pilsen. Seen a ton of gentrification, for better or worse, but some great food and cocktail bars around the area.

- The Blue Line goes straight down the Eisenhower (I-290). Doesn't, technically, stop in neighborhoods like North Lawndale and Garfield Park. Yes, it is bordered by both at a couple points, but accessibility to the train is a definite issue for some of the population in both. Plenty of people take the Blue Line from Forest Park and Oak Park. That won't be your worry. Coming back at an off-peak time is when it'll be a bit less crowded once you leave The Loop. At that point, just be alert as you would in any other major city. If you're uncomfortable, sit in the front car.