Visit this abandoned hospital (where Hillary Clinton was born!) by taking the red line to Bryn Mawr. Once you're there, walk to 5700 North Ashland Avenue and take a couple laps of the block to see how many people are outside. Usually, it's about a million. I swear, no one in this part of the city ever goes to sleep. They'll all be sitting on their porches waiting for you to walk by. If you're lucky and there's only minimal surveillance, sneak through the fence in the back and make your way in through the back of the building. There is a door, but if it's blocked off you can climb over a small brick wall to access an easier entrance through the east side of the building.
Safety and Risk
Edgewater is an easy place to get to, but not an easy place to get into. I visited the week before Halloween and was surprised by caution tape, screaming red signs, and archaic-looking metal plaques proclaiming the site's dangerous nature. I've never been somewhere so determined to scare you. It was wild. I've only made it inside the building once, and as soon as I was able to walk into the hospital lobby, I saw car headlights stopped outside and only narrowly escaped. Don't come here unless you're at least a little bit okay with the possibility of getting caught.
Chicago Pedway System
If you're looking for a way to explore some underground tunnels that aren't illegal (imagine!), there's no better place than the Pedway. Chicago has a huge network of connected paths that will take you almost anywhere in the business district. Click here to see where it can take you - and enjoy traveling through a less-crowded, less-frigid Chi-town! (Disclaimer: Pictures above aren't mine... I ended up just taking video footage. See below!)
Welcome to my favorite adventure site in Chicago, the ancient Damen Silos! Located at 2860 S Ashland Ave on the south branch of the Chicago River, they're relatively easy to get to without being super public. The easiest way to access the Silos is by taking the Orange Line on the CTA 'L' train to Ashland. If you are driving, this website gives detailed instructions for parking at a nearby Target.
From the L stop (or parking lot), walk through the business park until you're halfway down the fence and crawl through the hole directly across from the warehouse. You should see something similar to the images above - that's how you know you're at the right place. Once inside the fence, you can explore the abandoned warehouse and silos without much trouble, as long as you keep inconspicuous.
Offering its own sort of adventurous charm, the warehouse has three crumbling floors of colorful graffiti and artistically-disheveled metal. If you were a fan of Milwaukee Wisconsin's Solvay Coke & Glass factory (rest in peace, my friend), you'll absolutely love this place. The building is almost identical in structure.
Climb in through the hole pictured above (located on the silos' north side) and explore the cavernous tunnels of the silos! The amount of rooms and walkways seems endless, so be careful not to get lost. If you have stronger upper arms than me, you can probably climb to the top on the rope, too. It's located on the building's exterior on the river bank side, accessible and hidden from view.
Safety and Risk
If this place's risk-of-getting-you-arrested was on a five-star system, it would be a solid two. There's a security guard that patrols the site and does a few rounds at night, but he's fairly easy to avoid. He sits in a car with a flashing green light at the top, but he'll turn off the light if he's trying to sneak up on you. I haven't been caught by him, but some friends who have said he just gave them a stern warning and told them to leave. Doesn't sound too risky to me! Nevertheless, be careful swinging your flashlight or taking pictures with flash if you're visiting at night. The windows in both locations make it easy to give yourself away.
I know WAY TOO MUCH about this wild place. How much, you ask? Click here to read one of the longest essays I've ever written about the history of the Damen Silos. It's entertaining, I promise.