Chicago is a big city, with miles of roads, sidewalks, bike paths, train tracks, and waterways. In this week’s installment of the Our Fave series, we wanted to put those long stretches under the microscope and look at our favorite segments of travel: a couple miles of road, an el-stop to an el-stop, a bus route, section of the lake path, stretch of the river to kayak down, and so on …

Steven says:

Lake Shore Drive from Belmont to Mich Ave. Driving my sweety to work in the morning is the best 5 minutes of the day….you have the sun rising over the lake on your left, the temp is around 60-65 (at least for the time being), possibly some kayakers/canoers in the small waterway on your right…plus a great view of the high-rises as you approach downtown. Just a classic stretch of road.

Officer Gleason says:

I drive all over the county, but I’m usually on the South Side. My current favorite stretch of road is currently Stony Island to Cornell, Cornell to Hayes Dr/63, Hayes/63 to Lakeshore Drive to 57th. The Parks, the trees, the landscaping, it’s been an amazing transformation over the past five years. It’s also a great drive because this is typically my route home.

Another great drive is east bound on 75th street from the Ryan. The scenery changes dramatically with each block, but some of these houses are incredible to see. In fact, there’s one house that has a yard that you have to see to believe…

Another great, short drive is South Chicago south of 83 and around Bowen High School. Bowen is in need of a some repair, but the building itself is a very impressive red-brick structure. Bowen currently has 5 schools within its walls, and to the best of my knowledge, it is trying very hard to turn itself around.

Jennifer says:

I’m with Steve on LSD, so to speak. Lower Wacker is a must experience, too. My other favorite stretch of urban driving is Milwaukee beginning right around the Matchbox bar (Ogden Ave) and heading south. You pass a bunch of cool old brick buildings on the left, cross the expressway, and then Milwaukee ends at this incredible vista of downtown right at Blommer‘s chocolate factory, so if it’s cranked up, that corner also smells unbelievably great.

If you proceed south on Desplaines, you cross the wide open train yard and see more great city vistas, and then if you take that a little further to Lake, you can head east into the loop right under the el tracks, which are fun to drive under and which cast amazing shadows at certain times of day. I love that route into the city. Even if it is a bit idiosyncratic.

Nikkos says:

My weekend ritual (weather permitting) is a brisk bike ride (and by brisk I mean what my grandma used to call “breakneck speed”) from my humble environs (circa North and Ashland), down Cortland to Armitage, through the LP (outta the way Trixies!), across the bridge next to the LP Zoo (GREAT view of the ponds and skyline to the south), then down/up/down/up those bowl-like depressions in the park to the big hill (by Chicago standards) that leads down to the North Ave bridge. Once over the bridge to the lakefront path, I’ll just ride til I feel like turning around….and then on the way home I’ll hit Miko’s Italian Ice on Damen for a small coconut/mango combo.

Perfect.

Lauren says:

Damn, you just can’t match LSD. But, in favor of not wanting to sound like everyone else, I will have to settle with something else. Two something elses to be exact.

Favorite stretch for driving – Any of the small residential streets in Chicago that form the tree canopies in the spring and summer. Like Webster between Clark and Southport. All of the trees planted on either side of the street become all full with leaves, and intertwine above the road with the trees on the other side, forming an amazingly beautiful green umbrella. It just feels so cozy to drive underneath them.

Favorite stretch on the El – On the Brown Line around the loop. I know, it is SO cheesy and obvious. But it is also the very first train route that I ever took through the city, and it always reminds me of being younger and marveling at the amazing architecture downtown. I hardly ever get a chance to take it since I graduated from Columbia, but savor every chance I get.

Officer Gleason (again) says:

The Museum campus. Solider’s Field, the Shedd, Adler, the Field Museum. Tree-lined boulevards, wonderful buildings, gardens, lakefront. Hot damn, you have it all.

Alana says:

There is nothing more certain to make me giggle than riding in a pack of 20 vintage motorcycles around the soft curves of Lake Shore Drive, then gearing up to haul through the undercurrent of Lower Wacker. The reverberations, the throaty enthusiasm of bikes allowed to stretch out, all the red tail lights stretched out and springing back again like rubber bands, tipping right then right with the curves. Popping up to the surface, then a quick spin up the Kennedy to a well-earned beer.

Fuzzy says:

My motorcycle is not vintage — it’s just old. So while a 3 am tear up LSD is fun, equally delightful is a 3 am amble up Inner Lake Shore/Marine Drive, just inland of the Drive. It winds gently through the parks and there’s plenty of stop signs to remind you to… stop.

And when I’m not on a bike, I’m on the CTA tip. There’s a spot of the Red Line between Wilson and Sheridan where the track curves reeeeealy sharply, and if the train is going fast enough, it tilts a little and it feels like you’re going to fly off the tracks. Whee! Again!

Blommer Chocolate Company
600 West Kinzie St
1-800-621-1606

Lincoln Park Zoo
2001 N Clark St
312-742-2000

Miko’s Italian Ice
1846 N Damen
773-645-9664