I did two Rapha club rides when I was there for a weekend. Had a blast in both, and ended up gaining a very close friend I still speak to regularly even though I live in Montreal. This was 4 years ago. Every year since we go to Mallorca with a couple other friends from each city. So yeah the community there is great for riding
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What did you think of the neighborhood the rides start from (these were starting from the store, right?), WickerPark / Bucktown? I had suggested this would be a target neighborhood for the first year to the OP should they make the move based on some additional details I got.
It’s ten miles from Rapha Clubhouse to Pony Shop in Evanston. From Pony Shop, you have 20 minutes of riding north to get into the good riding areas.
It’s a nice area, but every single ride will involve riding someplace to get to someplace to ride. Not a good area for riding. Top of the screenshot is where the actual riding starts.
To get to any decent climbs in WI, how far are we talking? I regularly ride 5-6 hours, so don’t mind the flat lands if I can at least string together a route with some variety.
The SE section of WI has some fair climbing, but the “real” climbing is to be found on the Western side of the state. Again, mostly rollers and such, I believe (If strava categorization is reliable) we have a few cat 3 climbs in the state (Rib Mounting and at least one or two over by Sparta/Tomah). As stated elsewhere our race scenes focus on crit & CX racing. Up in La Cross WI there is an early season road race and typically we have one in New Glarus every year too (usually towards the end of the road season). Both in our hill zones. I don’t believe those areas are close enough to ride to.
I have every confidence you will find a good group of cyclists to hang around with.
I spent some time cranking watts on the Cal-Sag trail system around the Chicago land area and it was nice but multi-use so you do need to pay attention for pedestrians, roller-bladers, roller-skiers, slow cyclists etc.
I live in farmland in WI and so I’m instantly on quiet roads I don’t have any confidence those will be all that close to you.
I am currenlty mostly indoors now and typically breakout to the roads in March. Given that 45F feels warmer in March than it does now.
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Side tangent here but…
I used to think the same thing but I’ve made a couple moves in my life and they’ve all made a world of difference. From my tiny hometown to an amazing college town in Southern Indiana, then from Indianapolis to Northern California. Each move improved my life tremendously.
I went back to Chicago for an April wedding- it rained and SNOWED and I remember feeling awful. And then I remembered that’s just how I felt all the time when I lived in that region. It was a huge realization how I thought being sad all the time was normal.
It’s not as bad has you remember it. The road opens up just below where it says West Ridge on your map, which is 35min in, it’s then about 30min before you hit Sheridan or Green Bay road for the meat of your ride. 35min isn’t too bad for a warm up though. When the stops are dense, they are dense - in fact, it’s better not to use road pedals with plastic cleats because of the number of stops; Speedplay / MTB metal cleats are much faster to clipin.
For a weekday-lunch ride, you can hit Elston Ave right there for a workout. It’s got mile long stretches, a bike lane, not much traffic, etc. . Off hours, there is also a 3mile long raised trail right there, which would be good for a quick workout. The other ride you from there, is the Lakefront, which is 20min. If you get out in the early AM, it’s not so bad. Also, as you live there longer, you learn how to keep the ride moving by taking the right streets.
I would also argue that most people need to ride about an 30min to hit riding options, to get out of your local area. I’m in the burbs, and it’s 25min to get past the lights/stops. I can only think of Portland OR and the San Diego north-burbs, near the ocean, where you can get out and get to the meat of your ride in 5min.
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Hey, listen … sorry you didn’t like it here, but the Chicago metro area has ~10 million people, and tens of thousands of cyclists, and/or people who recreationally ride bikes for commuting, pleasure, etc… We’re not all sad and depressed.
I actually think that Minneapolis has a more lively and active cycling community than Chicago, and it is WAY colder there on average. They fat bike on frozen lakes … which seems awesome🤘
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Until you realize it’s July…
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Minneapolis is the frozen version of Seattle….in Seattle, they just accept the rain, throw on the Gore-Tex and get on with life. In Minneapolis, they dress as needed and do the same.
I have always loved the Minneapolis attitude towards cold….they just freaking embrace it. And it is spectacular there in the summer.
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The fat biking down in Palos during winter is pretty good. When cold enough, same, can ride on the frozen lakes.
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That’s a great way to get miles in. Can ride for hours with no traffic, other than the odd road crossing. When you get further away from the usual entry points/parking lots, the volume of other non-bike users diminishes quickly. It’s a bit boring though.
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For sure this is true
says the person who doesn’t race cross. cross is joy.
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did i stutter there? 
If Chicago is bad and Minneapolis is worse…then Ottawa is the place to be. I live in Ottawa Canada. Whatever Minneapolis does we get colder. We have this odd habit of a warm day in March with the sun shining, snow still on the ground and people will be wearing shorts. For your pleasure a quick link to see the difference. Ottawa is just that bit colder all the time.
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Moving to Chicago doesn’t mean you’ll live there forever. Advancing her career may open up quite more opportunities over time.
We’ve prioritized our life choices with a long term view which means we can now live in a mountain town in Oregon that checks all the box for us.
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Can we talk about endless winters and subzero temps or really anything but cross
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