Apologies if this is a ridiculous question but is biking on the southern half of the lakeshore path safe in the evenings? 

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Yes, I've done it many time and I live on the north side, in Albany Park.

It's well lit and easy to follow. The new underpass south of the Aquarium makes it easy and safer to cross which used to be a busy road.
It's actually pretty nice because there's so much fewer people than the north side, but the pavement tends to be a bit rougher.
i think it may actually be safer than the northern part. i would anticipate more predators on the northern portion
On north or south side, it pays to be more aware of your surroundings in areas where lighting is inadequate, or where shrubs and trees that may conceal a person are close to the path, especially if you're riding alone.
I've ridden this many times and have found it safe for the most part. The only area I've ever encountered a problem was by 31st Street Beach. I had a group of kids run at me one night like they were going to do something, only to back off at the last second and run off laughing. I almost lost control of my bike and could've gotten hurt. However, I've ridden this same area many times in the daytime and have never had a problem. I chalk up my experience to bad luck, and just some random A-Holes who got a kick at someone's expense. Like any other time, just be alert and you should be fine.
Answer: yes.
Thanks, I was referring more to the high crime in general on the south side and if it spilled over onto the path. I've had a few run in with 'thug' types the few times ive been on it
XV said:
Thanks, I was referring more to the high crime in general on the south side and if it spilled over onto the path. I've had a few run in with 'thug' types the few times ive been on it

I suspected that.

I've ridden it several times, never had a problem. Of course I'm an old guy and probably look like a bum so maybe I'd be a bad target, not worthwhile.
The North Side is where all the cool people live, WINK! But I certainly love riding the South section of the lakefront trail. After you get through all the chaos on the north side (Volleyball dorks, tourist, and just bad trail etiquette behavior, I swear, I t-bone a jogger every year, first response is always if you didn't have those damn ear buds in you would heard me yelling at you on the left!).

About museum campus all the way past Promontory Point is great, few rough surfaces, but by far the better section. Though many would boo hoo, I ride in the late evening out there due to even less summer traffic. Just use good judgment (street smarts, ride away from sketchy behavior)! My late night advice is ride with a friend. Numbers always provide protection. Have fun and look out for the buthead going too fast, me!
My advice for any path you think is "sketchy" was learned from experience on the IPP one night riding through Bellwood. Never pass through a group congregating in the middle of the path. I did with a polite "thanks, dudes" to be thanked with a nice sucker punch to the jaw. Thanks to my Giro helmet and using my 1980s vintage Cannondale beater bike as a shield, I escaped with only bruises and cuts. When in doubt, follow your gut instincts.
Yikes!

Chris Hainey said:
My advice for any path you think is "sketchy" was learned from experience on the IPP one night riding through Bellwood. Never pass through a group congregating in the middle of the path. I did with a polite "thanks, dudes" to be thanked with a nice sucker punch to the jaw. Thanks to my Giro helmet and using my 1980s vintage Cannondale beater bike as a shield, I escaped with only bruises and cuts. When in doubt, follow your gut instincts.
Are there any good ways to avoid the navy pier bridge clusterfuck when getting to the south part?

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