Your first stop in this guide takes you to Swallow Cliff Woods. It’s an 800-acre forest preserve located in Palos, IL, about 25 miles (or ~40-minute drive) from downtown Chicago. Its best-known feature is a former toboggan hill that’s now used by fitness fanatics, and this is where you’re starting.
This is a shot from the front of the Swallow Cliff Stairs, which lead up to a 100 ft bluff. On any given day, you’ll find scores of folks doing laps up and down these stairs. Even walking up once left us a bit out of breath — kudos to all those doing multiple laps and getting fit.
Initially, six chutes ran down the top of the hill to the bottom. You’d load up your toboggan and send it down these chutes. Those got closed a few years back due to safety and maintenance concerns, but when winter rolls around, the hill is opened back up for sledding. Bookmark this for winter — this is one of the few sledding hills in Chicago that’s lit up at night.
A lap counter at the top of the staircase helps you keep track if you’re here to run laps. When all the counters are in use, many people collect little pebbles each time they complete a lap, instead.
After you’re done with the stairs, stay at the top, and you’ll find a small connector trail leading you to the forest preserve’s yellow and brown trails.
Below is a picture of the trail map. In the middle of the map, there’s a dotted gray line next to where it says “Swallow Cliff Woods.” The top of that gray line is the connector trail where we started. It’s also where the Swallow Cliff Stairs are located.
We took the connector trail to the yellow course, which is about an 8-mile loop.
If you don’t want to do the entire loop, you can head West from the bottom of the connector trail to get to the Yellow trail, which will eventually take you back to the cliff stairs. That route is about 4 miles.
Part of the hike features these long and wide trails that cut deep into the forest. The massive trees on either side make it feel like you’re going through a tunnel. 
As you make your way through the main trail, you’ll see signs for small trail offshoots that are only open to foot traffic. Explore these for an even quieter and more solitary experience.
Just a few miles from Swallow Cliff Woods is the Little Red Schoolhouse Nature Center. We’re here because we can’t get enough of the outdoors. For reference, the Nature Center and Grounds are open from 9 am – 4 pm.
On the grounds is a nature center and a 2-mile trail that takes you through the forest grounds. If you have kids, this is an excellent alternative if the Swallow Cliff Stairs and subsequent hikes are too intense.
The Nature Center isn’t big, but they pack a lot of exhibits into their small space. You’ll find large predatory birds and educational exhibits, and you might spot a few reptiles in the swamp behind the Nature Center.
Halfway into the trail, you’ll be deep into the forest grounds, and what you’ll run into is the site of an old log cabin school built in 1836. While that school is now demolished, you’ll find a small memorial on the site. Some say you can still hear the sound of small children laughing in the woods. I just made that up, but wouldn’t that be a spooky way to end your day?