For your bike ride, you’ll be following the Des Plaines River Trail which extends from Wisconsin and goes all the way to River Grove, IL, just west of Chicago. You won’t be riding the entire trail, but we’ve got you starting as far north on the trail as the Metra will take you.
To get started, you’ll be taking the Milwaukee District North (MD-N) Metra Line. We jumped on at the Grayland Station in Old Irving Park, but depending on where you’re at, here are some other stops in the city that might be more convenient.
1. Union Station (Downtown)
2. Western (West Town)
3. Healy (Hermosa)
4. Grayland (Old Irving Park)
5. Mayfair (Old Irving Park) — also next to the Montrose Blue Line Station
Since you’re bringing your bike, here are a few rules to keep in mind when bringing it aboard the train.
– Bikes are only allowed on weekends and off peak hours
– You can only have bikes in the ADA accessible cars – basically every couple of cars are ADA Accessible
– Secure your bike onto the lower bar of the ADA seating with a bungee cable (our set up is below)
– If you have the Ventra App on your phone, you can purchase tickets directly on the app after you board the train
From here, you’ve got about an hour until Libertyville so take the time to relax and mentally prepare yourself for the long bike ride back.
The Libertyville Metra station is as far north as the train will take you while still being close to the trail. We’re so far north that you can actually take the trail north and bike to the Wisconsin border in about 1.5 hours. For now, we’re saving that trip for another guide.
After you deboard the train, you’ll find yourself in a picturesque downtown square full of cafes and boutiques. If it weren’t for the long trek ahead, we could’ve spent a decent chuck of time exploring.
Instead, we just did a quick jaunt through Libertyville’s main downtown strip that follows Milwaukee Ave. This cafe marks the end and from here you can veer off to a side street and make your way to the trailhead. This is also your last chance to grab a bite to eat before beginning the ride.
The trailhead is a quick 5 minute bike ride from downtown Libertyville. From here, you’re about 34 miles to Gene’s and Jude’s. According to Google Maps, that’s about a 3 hour bike ride. According to my couch potato fitness level and ill-suited bike tires, this was closer to 4 hours.
The main issue was my bike. I used a normal road bike with 25 mm width tires. Most of the trail is packed dirt, which my bike actually handled well, but parts are crushed gravel that was slow to navigate at times. While I made it, you’d be better off with at least 32 mm tires. Here’s a handy primer on bike tire sizes.
The trail closely tracks the Des Plaines River so you’ll be riding over lots of bridges and through underpasses. While these are fun trail artifacts, there’s a tendency for underpasses and significant sections of the trail to flood after heavy rains. Before you ride, you can check trail status here.
About 1/4 of the people we saw on the trail were lugging a rod and tackle with them. For all you fishing enthusiasts, make a note of all the fishing spots along the river for a follow up visit.
Most of your ride will look this this — where it’s just you and the meditative sound of your bike crunching the dirt beneath it. If someone could make an hour long loop of that sound, that would totally replace my ‘waves crashing’ sleep soundtrack.
These strategically placed benches along the trail always seem to appear right when you need one.
The trail runs through a couple of different forest preserves and at certain points, you’ll see absolutely stunning home like this one which has the entire forest preserve as a backyard. Firing up Zillow on your phone and doing some house daydreaming is another reason to add some extra time into your ride.
About half way through the ride, the trail will cross from Lake County to Cook County. Each county takes care of their own section of trail and Cook County’s portion is noticeably rougher. This is where I wish I had fatter bike tires. 
If you had the proper tires, the Cook County side is probably more fun to ride if your definition of fun is something closer to a mountain biking experience. Here’s a closer look at the trail and what most it looks like. There are sections that are even rougher, so keep all this in mind as you plan your trip.
About three or four hours from the start of your ride and with over 2000 calories burned, you’ll have finally made it to Gene’s and Jude’s, located right off the trail in River Grove, IL — just west of Chicago.
This place is all over any of those top Chicago hot dog lists. If there was a Mount Rushmore of Chicago hot dogs, then this place would be Gutzon Borglum, the famed sculptor and creator of the monument.
Gene’s and Jude’s is home to the home to the prequel version of the Chicago-style hot dog. This is the Depression Dog, the original variant. It starts with a thin and almost chewy steamed bun and holds a hot dog, mustard, onions, and sport peppers. It’s then blanketed in fries and wrapped up in wax paper.
Their menu is simple. You either get the single dog or the double dog, which is two hot dogs in a single bun. Just my personal suggestion, get the single dog or two single dogs instead of a double dog. These buns aren’t engineered to handle two hot dogs.
A few things to note on your visit.
– For the longest time this place was cash-only, but they are finally accepting credit cards!
– No ketchup on anything, not even the fries. You thought Chicagoans were militant about ketchup, this place is next level with that stuff.
– No indoor seating. Everyone just eats on top of their cars or wherever they can post up in the parking lot.
After you reward yourself with as many hot dogs as it takes, you’re just a few blocks from the River Grove Metra station which will take you back into the city. Now the question is: will you go even further for a hot dog?
