I lived in the Washington DC area for 50 years and have been a cyclist pretty much my whole life. I recently spent 2.5 years living in Chicago, and I was surprised by how much less I enjoyed biking there. As many have said, the terrain is dead flat, but also, the roads have few turns. These affected my ride enjoyment more than I expected. I found that most people rode the same route - up Sherman Drive toward Wisconsin. The bike paths along the lake are heavily used, but not for serious biking IMO. As I recall, the Des Plains (sp?) gravel trail was a straight, flat, gravel trail along a power line corridor. I did like Wisconsin the few times I loaded up my bike in the car and did the 2+ hour drive to those spots. Chicago is a great city and the group ride out of Wicker Park full of nice people, but dont expect dramatic terrain for your outside rides.
Thanks for all the replies, I have to say I didn’t expect so many people to have so much input!
It sounds like while I will miss the hills, the group ride scene is still pretty good. I definitely still need the weekly WNR type events.
There are tons of these to be had. And also early morning groups
No….not even close. Only one section up north runs along power lines and it only lasts for a couple hundred meters. The trail roughly follows the Des Plaines River, not power lines.
And while there are certainly a lot of straight sections, we have a blast railing turns and trying to drop buddies on our group rides.
Lived most of my life in Chicago’s N and NW suburbs. I love this area, the local crits and the family vibe of my local group. But agree with others on the geography. My group does a week every spring in N Georgia just to ride mtns. When I get home – from there or some lucky trips riding in Colorado, Bay Area, or Los Angeles – I feel like a conscript back from furlough: Re-entry hurts! Easier, emotionally, not to even leave the cage? Few have posted on our suburban drivers: They suck. Riding in a group is fine, but when I bike commute I feel like there’s a target on my back. If you ride solo here, get obnoxiously bright lights & be careful.
We’re neighbors!!! Highwood here. And I echo everything you’ve said about cycling. Not much more to add!
If I lived in Highwood, you’d find me in one of only 3 spots….Tala, Beermiscuous and Kings & Convicts.
But mostly Tala….we are usually there every Friday AM for our most social ride of the week. Love that place…
This should be pretty cool once it is completed….
ETA - paywall free article below
When I ride with a group … and I rarely do … I ride with the Klick crew. They take off from about a block away from my house and they do their mid-ride stop at Tala in Highwood. That place seems like a pretty popular cycling hub?
As an aside … last summer (2021) I did my first post-pandemic group ride with Klick for race prep. I didn’t know anyone, and some dude shows up on a gravel bike with skinny tires and a handlebar bag 
He was also a super nice guy … they were all giving him good-natured grief about racing Cat4. I didn’t know anyone/anything so I just listened and rode along. During every group sprint this guy just drops us all — by A LOT. Like, I’m not a sprinter, but it felt like I was standing still.
I’m thinking to myself, if this guy is a Cat4 why am I even bothering with racing? It was demoralizing. Turns out he goes from Cat4 to Cat1 that summer, and this year he took a bunch of wins and podiums in big races like TOAD, etc, and I think he even won some hardware at the state track championships at the Northbrook velodrome. I felt better about racing again 
This story has no point … just a bike story about some guy in Chicago that made my eyes water 
Definitely…IMO, the best damn coffee shop in the area. We go every Friday AM during the season.
The donuts are from Gurnee Donuts and some of the best in the area…basically the same donuts as Lee’s Donuts in Libertyville. If you haven’t tried it yet, get the blueberry donut next time you are there. Worth every calorie!!
Spunky Dunkers is better.
Tip Hansa coffee in Libertyville off the DPRT has Lee’s donuts as well as their own stuff and is also a fantastic coffee stop.
Yeah,I’m in L-vile, but I’ve never been a huge Hansa fan….my daughter lovers it, though.
I usually hit Lee’s every Friday ( before riding to Tala) for #DonutFriday. Lee’s and Gurnee are basically the same, although unrelated. Local lore is that the original owners of both were friends and shared recipes.
ETA - I hit Duck Donuts today instead of Lee’s as a change of pace. Every single donut is made fresh right in front of you. This morning’s selection…
That’s a huge knock against it. Absolutely fresh donuts, and most baked goods for that matter, aren’t anywhere near as good as ones where the oils have settled and the caramels have stiffened.
Eh, try ‘em and see…it is actually a really solid donut (if pricey).
Still prefer Lee’s, but these are a nice change of pace occasionally. The biggest downside is that every base donut is the same, the only thing that changes is the toppings.
You ever listened to anyone from Filthy-Delphia? For like 14 seconds?