Do you have a link to the route you can share?
I’m always on the lookout for new routes. But, lol, I’ll never make it to a ride that starts at 6:30AM … I’m an early riser, I need a few minutes in the morning🤘
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KG is still slogging away with us….MZ has since moved to NC.
This is from Libertyville, but if you just lop off the stuff before Deerfield Road ( and the return back north), that is pretty much the route from Deerfield.
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Also, I forgot about the Chicago Cyclocross Cup - which is a 9 race series from October through December.
I abstain from cyclocross for religious, moral and ethical reasons and am in many ways opposed to the stain it casts on cycling 
but there are heathens and other wayward souls who like to carry their bikes up stairs and run on grass in footwear ill-suited to the task.
(At this point I think this thread is just Chicagoans talking amongst themselves, but I’m here for it)
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I am just going to say my opinion and no I did not read all the other comments.
If your life is 100% cycling focused, Chicago absolutely sucks to live in from that perspective. If you happen to be an open minded individual who likes lots of art, food, entertainment and “lifestyle” and just happen to love cycling then Chicago is a awesome place to live!
You can adapt to the riding style in Chicago, but as said, if life=cycling then just don’t move here, you plain and simple will not be happy.
I would recommend you check-out North-West Indiana (Valparaiso, Chesterton specifically). The cycling is AMAZING out in that area and they have tons of MTB options and the roads are slightly rolling but very safe, quiet and literally in the middle of no where. The cycling community is crazy strong, the only downfall is the roads are a little junk and would recommend a minimum of 28 tires. The drive to the city depending on where you going isn’t too awful. The cost of living is much cheaper etc etc.
Send me a PM if you want more information
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Thanks! Currently my life is very cycling focused. I’d be there 2-3years before being relocated back home. I can live with flatland for a while if there are groups and communities to interact with, but i would find it hard to give up that along with good terrain, and my job (which I’ll also need to leave if this goes ahead) all at once.
I’m a roadie who likes to climb, never done crits, but might be a nice change too.
Shut up and jump. Its 3 years, you will never regret it. You would regret not doing it 40 years from now. Just do it. Nothing anyone here can say can prepare you for how much of a different world it is. If 20 years ago me had that chance and didnt take it, i would never let them live it down.
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FWIW I grew up in Michigan, near Chicago. There are a lot of things to like about the Midwest, when I was growing up we spent June at our cottage on a lake. And skiing in the winter. After graduating from college I moved to the west coast and have lived in California and Oregon for 36 years. If you’ve live near mountains, you become spoiled. But sacrificing that for a couple years to help partner’s career? That’s something I would likely do, or ask the partner to explore jobs in the mountain states.
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One more then i promise i will cut it out. You can take a train to detroit and race maidson worlds at the lexux velodrome. lexusvelodrome.com
Thank god we can upload gifs again 
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It needs sound though or you might think its Russian
This thread is fascinating as I grew up in the Chicagoland area, lived in Utah the last 20 years, and my wife and I kick around moving back. I’ve thought “what would I do with myself” since I picked up cycling out here and get obsessive. With a little zoom I can see the house I mostly grew up in on this map, makes me think moving back is much more viable.
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I grew up in a small town in the Netherlands and at age 28 , was offered a job in Chicago. The original plan was to try it out for a few years and then re-evaluate.
Almost 26 years later I am still in Chicago and have become a US citizen.
Growing up in the 80’s cycling was a part of daily life as it was my main mode of transportation. In addition, during the first mountainbike craze in the mid-80s we would do gravel rides every weekend (decades before that term became a buzz-word). I still fondly remember my rigid steel Diamondback with BioPace chainrings
Chicago is of course significantly different than the Netherlands in almost every aspect imaginable, from bicycling to language, city size, diversity, food, housing, etc. I still remember the first time I walked under the ‘L’ to my new job. The noise of the city and amount of people going to work was absolutely overwhelming. Yet I’ve come to love it here. I met my wife here and live in a great north-side neighborhood.
I nowadays ride more for fun, weekend coffee rides to Highland Park or Lake Bluff for example, places which make for great riding from Chicago.
My point is that, yes, it can be unnerving to move to Chicago from another country. But approach it with an open mind (both bicycling and otherwise) and you might be surprised how great this city is.
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Life is what you make of it. I cant believe if you like to cycle Chicago will end your enjoyment. I live in Ottawa Canada. Ottawa is a lot colder then Chicago with more months below zero and more snow. If I were to move to Chicago I would get at least two more months of cycling outside. I just ride the roads. Lots of Ottawa riding can be flat. Go south and it is flat. East or west dont have much elevation. If you want hills you need to go north into Quebec. I ride more inside then outside…I enjoy being on the trainer at least twice a week all year. I ride outside from April to October. We all have different likes and dislikes. Chicago doesnt look terrible to me.
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Speaking of cottages… the planning a week in the spring/summer/fall around Traverse City Michigan is well worth it. Fall cycling (and leaf-peeping) on the Old Mission Peninsula
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My parents bought on a little north of there, near Boyne City, on Lake Charlevoix. Beautiful lake, beautiful area.
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I was just there 8 days ago for the inaugural Belgian Waffle Ride - Michigan. 75 miles and ~5500 feet of climbing. “Flat” is not a problem up there, punchy hills that will grind you to dust 
Some photos from my recon ride at the 45th parallel the day before the race. Pretty sweet🤘
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Looks sandy, Hope you put 45c tires on!
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I don’t have much insight, but Chicago was the biggest city near my tiny hometown, so I spent some time there and have friends who live and have lived there.
My biggest input is once I was back for a wedding and struck up conversation with several people who moved from Chicago because they were into cycling. I think there are a couple group rides, but I get the impression it’s all 'burbs and crits (and maybe good cross racing?). Not my scene but could be for someone else.
I get the same impression. My SO joke that if we moved “back” (we’re from Northwest Indiana but Chicago or Indy is the closest we’d tolerate to our hometown), we’d probably get a peloton and start doing Crossfit.