Moving - Sydney to Chicago

Hi there,

I am in the process of considering a move from the sunny North Shores of Sydney to Chicago with work. I am keen to keep on riding (of course!) but am not sure of any clubs/ racing/ rides etc in Chicago.

I have raced TT, Cyclocross and some limited Crit Racing. Are there any must do events in the area?

Look forward to hearing from you!



Try the USA Cycling website for USAC sanctioned events in the Chicagoland area; keep in mind this likely will be updated since we are in the middle of winter up here. Also, hook up with a local bike shop as they are a wealth of information regarding the biking scene. I’m sure others will chime in soon.

There are tons of crits, cyclross and TT’s – Chicago is a HUGE metropolitan area, so most of these will be be a bit of a drive.

Check out USAC website and and – all are good resources.

The only thing we don’t have around here in abundance is gravel and road races (which are my two favorites…most of those are a 2-3 hour drive away)

If you move to the north shore of Chicago (or in the city itself) there are too many cycling clubs to count.

The cycling community here is robust – but I will tell you… the winters are no bullshit. Riding is hard during the cold months, so there might not be a ton of current info right now.

Hope this is helpful.

The intelligentisa cup in the summer at the end of July is great. A 10 day road/crit omnium race.

For cyclocross check out 100+ entries in the Cat 4/5 are typical during the early races in the series.

Just north of the border around Milwaukee is
11 straight days of crit racing.

20 miles southwest of the city there are great MTB trails near Palos Hills.

This. I moved from Sydney and lived in Chicago for 5 years. Nothing prepares you for -40c. Sydney thinks it has winter as a season, I learned it only has Summer and Better Summer as the seasons.


In addition to what was already said above, there was a post in a reddit forum about road racing near Chicago just a couple of weeks ago, so you might find this helpful as well:

There’s a lot of road racing options in and around Chicago, once it finally warms up. Time Trials are fewer and further away from the city proper, and there is a healthy CX scene that you can race almost every weekend from September through November with deep fields - especially in the lower categories.

There are many clubs in Chicago, each with varying degrees of size and competition focus. xXx Racing is probably the largest, but there are others to chose from.

Winters here are certainly rough - with the weeks-at-a-time temps of -6C highs and the limited hours of daylight once the time changes (in early November through early March the sun sets at 4:30 pm) outside riding becomes a challenge. However, since you’re likely a loyal TR user, you will probably be used to the indoor riding requirement. Group rides on the weekend are well attended and have varying degrees of organization, but there’s almost certainly a group that you can find to match your aims for the day.

Finally, ALL route options around here are extremely flat. As in, 609m of elevation gain in 180km flat. There are, however, plenty of opportunities to ride up a “Belgian Mountain” on particularly windy days. Depending on where you live, route options can be a bit limited for training, and unless you’re living somewhere in the suburbs it’s pretty hard to get completely “out” of the city. In my opinion, the city has great infrastructure for commuting/traversing the city.

As others have said, cross is pretty big here. Races are all fairly close to, or in the city, for the chi cross cup. There’s a few decent gravel races fairly close to downtown. Hour for one. Few hours for others.