This was the answer most recently when the question was asked: https://forum.slowtwitch.com/...ing=chicago#p6530628

Ohio Street Beach, http://openwaterchicago.com/ and Promonotory point are the in-city open water swim spots. There's a few masters squads though I'm partial to CMSC at UIC. https://www.chicagomasters.com/

The Lakefront is great for running early mornings but I'd highly discourage it for riding during the summer. Heading north of Evanston on Sheridan is where a good chunk of the great outdoor riding is done but there's a few routes West and South. I recommend Skokie as well. Trail running wise you'll end up needing to head towards the burbs or Waterfall Glen area to get away from the path.

Lincoln Park is pretty phenomenal neighborhood to raise a family in or even to live in otherwise. Old Town, West Loop, and South Loop would be the next few on my recommended list if you're looking to remain in the city and not the burbs.

Bike fit wise, I don't hesitate to recommend Anne Barnes at Live Grit or Adam Kaplan at Get-a-Grip.

Feel free to PM with any questions. jrielley is a local pro that's a great resource as well.

Welcome to the windy city Francois

Lakefront is indeed a no-go for cycling as it is too narrow and crowded unless you ride very early in the morning.

- north: typical ride is start on lake front all the way north and follow sheridan road... you can pretty much ride to Wisconsin
- south: ride to willow springs
- check the "Judson Ride" on facebook. Famous hardcore cyclists only ride starting in Evaston.

Otherwise there's multiple computrainer centers in the city.

Also:

Running:
- lakefront is great all year long (except in the summer it gets really crowded)
- Montrose track

Swimming:
- FFC has pools everywhere in the city

Yup on FFC. We visited the Lincoln Park one this weekend as we were home hunting.

Chicago is really big so definitely need to adjust back from small college town in Florida :)

Welcome to Chicago. There is great outdoor riding, but I'd plan on getting used to indoor riding, if you're not already doing it. It's hard to avoid given the six months of winter.

Aside from the Northern burbs, which you can ride to straight from the city up Sheridan road, there are also options out West, assuming you have a car. Barrington Hills is a common destination- it's really nice out there and you get some actual hills. Check out the CHicago Tri-Club for group rides and routes.

And coming from Florida, prepare for a totally different quality of road. It's rare that I do a ride without passing a pothole that, if I hit directly, would cause a flat or crash. This is particularly true in late winter/ early spring when the weather warms and the potholes pop up faster than the daffodils.

North Central Florida has its share of shitty roads because of the amount of heavy rain we get.
Some of our favorite roads have some major potholes...or maybe they're sinkholes, I can't tell anymore.

I ride a lot on the trainer even here anyway.

Got a cross/gravel bike? This is less than a 10 min ride from the end of the Green line (Harlem stop in Oak Park) and goes North to Wisconsin

That's perfect. I do have a nice Niner. This also looks like it can take a road bike. I'll be working in Maywood so not far from Oak Park. Plan is to live in East Village area though.

My propaganda only shows the nice bit of the trail. It gets rough in places. I've ridden it on a roadie with 25's, but there are some short stretches of dirt that will bog you down if it's rained in the previous few days.

Still, It's 10 min from my house, off street and shaded, so a good place to hit up when conditions permit.

If your looking for some group workouts that are a high level - Bishop Racing would be great. They are downtown.

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Those are nice. I think road bikes with decent tires are fine for those trails. I rode them a bit with 25s no problem.

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If you are working in Maywood and have school-aged kids, you might want to consider the western suburbs that feed in to the Hinsdale school district which is one of the best in the state. Plenty of good riding and running out that way too. Your commute to Maywood from the city will be an hour even though it is only 10 miles. Things to consider...

I have a couple of colleagues doing the commute from EV, and they live just off of 290.
They're in in 30min, 40min when traffic is bad.

A huge network of trails west of the city, the Illinois Prairie Path network and many many many connected and interconnected trails. You can do 2, 3, 4, 5-hour plus non-stop and, most important TOTALLY car-free loops, the sky is the limit. This is only a small fraction of the avail trails:



Sure, road bikes will work, but really only in the best of weather. The crushed gravel trail surface is not the best for the smaller tires and rim brakes. Gravel and CX bikes are great, the fatter the tires, the better. That way you can still fly when the surface turns muddy.

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FYI... Illinois Prairie Path is one of the first (if not the first) rails-to-trails conversions. Opened 1963.

Road: lots of groups and rides. The Judson group is a great bunch of people. Go to bike shops to find groups. I like the riding best west of the Fox River, but this is likely not very possible for you.

Gravel: the Prairie Path is indeed great, especially early AM or when it's cold and empty. You can get on fairly easily from the city, but it's not a short ride. Also, there are lots of fun true gravel events on the farm roads around here.

MTB: Palos and Kettle Moraine in WI. Both are surprisingly not bad.

Get a fatbike for the winter if you have room to store it. Learn to enjoy riding in the cold.

Also, when you get some time, come on up to Madison for some phenomenal riding......

I do work with Epic folks for some of my projects, and they're in Verona, so definitely happening.

I think you'll enjoy that. Let me know if you're coming up and need any info. Tons of rides and riders in the area and some nice wide open and hills routes. I love Chicago to visit, but riding up here is another world. Lonely country roads everywhere....

Enjoy the midwest!

Our group has a strong Chicago contingent (myself included) and we do a lot of riding north from the city, no lakefront path for me. Happy to show newbies the routes if you're interested just drop me a note.

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IL PIRATA VI GUARDA

Where is this. Along the Desplaines in Thatcher Woods?

Could you share a screenshot of google map of where this is? Movers will be here Monday and we'll be in Chicago Thursday next week.

Based on the description, I am going to go with a Yes, it is the Des Plaines River Trail. While this map (http://fpdcc.com/...-Trail-Map-10-15.pdf) shows the trail starting at North Avenue, there is a less maintained section that starts at Madison Street in River Forest/Forest Park and runs south to North Avenue.


And here's a link to the Lake County portion of the DPRT: http://www.lcfpd.org/.../7/DPR-Trail-Map.pdf

Happy to attend a Meetup / welcome to the city as well. I was just thinking earlier today that I wish I knew more triathletes in the city.

Here you go.