I am definitely looking for a road bike. My current bike is a 2015 BMC TeamMachine with Dura Ace, so I plan on getting something equivalent if not an upgrade - no concrete budget. I am strongly leaning towards also getting a cross bike for commuting/the winter.

thanks for all the responses - will definitely try to check out the recommended shops.

The north shore has a huge road cycling presence. Unfortunately, I know nothing about it he south side in that respect. I assume Hyde Park has cyclists, with UC and all. But none has written here that I noticed.

Winter is hard, unless you're a maniac. I rode all year in 2011-12 and decided a 2 month break from riding isn't that bad.

A cross bike is a good choice. You're not TOO far from trails at Palos.

Please give us an update after you've moved and found some things out.

Most of the good/big group rides in the city (xXx, CCC, Turin, etc.) start north of you and go further north up to the north shore. xXx Team Ride (I'm a member) is open to the public and is a popular Saturday ride. First half is no-drop and pretty social, but first 10-15 miles are stop-and-go on the way out of the city. Route extensions after the coffee stop are great. For a south side ride, the Lemont / Burr Ridge area has some great roads with rollers and low vehicle traffic. I've seen a group ride forming on the weekends starting at Waterfall Glen, but I've just ridden by on my own so not sure who organizes or what time it starts. The SE portion of this route is one I do frequently and is accessible from the city by taking Ogden SW to Plainfield Rd to 47th>East Ave>Santa Fe>75th>Willow Springs, though not sure the best way out there from Hyde Park.

Winter sucks. A smart trainer you can use with Zwift or TrainerRoad definitely helps, though myself and many teammates will ride down to about 10 degrees as long as it's not icy out - at least a few people tend to show up to just about every Saturday team ride throughout the winter.

CycleSmithy on the north side is a pretty good shop; I'd also second Kozy.

Welcome to Chicagoland
1. There are many, many riding groups in the city (as people have said, highly concentrated on the north side). You shouldn't have difficulty finding one but you might have to hike up north a bit (maybe). The riding around here can be great and there are lots of events in the burbs.
2. The 606 is cool but not for serious cyclists. The Lakefront is packed whenever it's nice and too twisty in sections for fast riding. The Lakefront is lots of fun in the winter, though.
3. BMC TM w/ DA? Not fooling around are you. Why are you selling it / getting rid of it? You can ride on the road much longer than you'd think around here with the right clothing. I've done many rides in the middle of January on a standard road bike. There are lots of great bike stores in Chicago, Kozy sells everything. Lots of cooler smaller shops as well.
4. A cross bike is a good idea, a gravel bike is a better idea. A road bike + a fattie or a mountain bike is probably the best idea (to me at least). I think fat bikes are very useful in the Chicago area and tons of fun to ride in general. You'll learn to love winter riding around here, with studded fat tires it's becoming one of my favorite times to ride.
5. The whole "Chicago is super dangerous" thing is kind of overblown. Hyde Park is just fine, like any other major city just use common sense. Hyde Park is a fantastic place to live.

My rules for winter riding in chicago are if it's above 40 I ride, if it's above 30 and sunny I'll ride. First time sand and/or salt gets put on road my road bike goes away and my cross bike comes out. First big rain in the spring I deal the roads clean enough for my road bike to come back out.

checkout southchicagowheelmen