Chicago Opinions?

Currently, I live in New Zealand, but my partner has a job offer in Chicago, and I’m doing some research on whether it would be a good place to live. Cycling is quite a big part of my life, which is where my social circle is, and where I spend more of my spare time than I like to admit.

NZ has great weather and roads, but is missing the cycling culture aspect prominent in many US cities. I know that Chicago is cold and flat.

As a cyclist, is Chicago a really bad decision? or can it be enjoyable? I do like riding hills, doing about 250,000m per year most seasons. Maybe I could get over that.

Really struggling with that the right call is right now, as its a great job opportunity for her.

Just to set expectations - Chicago is pan-flat. You can run a 1x with a 52T chainring and be just fine.

That said, I have lived here in the northern 'burbs for 23 years and there are a lot of riding options (except for MTB). The roads up near me are generally pretty good…I can go north into Wisconsin or West and find roads with not a whole lot of traffic. There are a number of different good, fast group rides up here and the Des Plaines River trail is a great option for gravel riding (if not terribly technical). It is ~110 miles, round trip and runs from just south of O’Hare airport all the way up to the Wisconsin border. You can also link it to some other trails like the Prairie Path trals and add on additional mileage.

City riding is a little more chalenging, with the Lakeshore path being a viable, but crowded option. I’ll et others provide more city options, as I am not very familiar with them.

Winter riding is tough, I’m not gonna lie. I basically ride indoors form November to April, taking advantgae of warmer days when I can. But my tolerance for cold is inversely related to my age, so I generally don’t bother riding outside if the temps drop below 40*F.

There is a LOT of outstanding gravel (and hills) in the Western parts of IL, but you are going to have to drive to get there…~2.5 hours usually.

For me, I have found you can find good riding just about anywhere you live…you may have to adjust what and how your ride, but there is always good riding to be had (and groups to share it with).

Chicago is a wonderful city with fantastic restaurants and vibrant communities…but it is cold AF in the winter and lots of grey skies. Honestly, I never thought I would live here as long as I have, but here I am 23 years later…


Chicago is a fantastic place to live (both city, and surrounding suburbs). No shortage of clubs and race teams, and a lot of events on the calendar especially if you include Wisconsin and Michigan. You might have to change your expectations with the type of racing, if you come from a road racing background. The Midwest is dominated by crits, gravel grinders, CX. It is flat in Chicagoland, but Wisconsin and Michigan have plenty of rolling hills. You can check out NorCal’s recent Intelligentsia Cup series to get an idea what the crits are like.


I think you are understating how hilly it can get with a 2.5 hour drive. While a 1x with a 52t chainring would be fine for Chicagoland, That 2.5 hour drive will leave you riding hills that make you wish you had a smaller ring than a 34t :grinning:


Thanks for the reply, to clarify I realise its pan flat, still deciding whether I would tolerate that haha.

I guess my questions are more around the community and whether it would be easy to find a group of linked minded people to ride with, as my social circle has always come from cycling. I can deal with good riding no scene, and bad riding good scene, but not sure I can live with none of these two. The other part im really on the fence about is whether that weather would simple kill me. Currently I ride about 750hours a year 95% of which is outdoors, and that doesn’t even sound close to possible in Chicago.

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This is a good point

Also where in Chicago matters. I have lived in various places in Chicago city limits and every ride involved riding to a place before riding was any good.

Where in Chicago? Suburbs? Which?

The western suburbs (Hinsdale area find it) have some great groups and varied routes. North shore like Evanston will have you on the same roads a whole lot of the time. Evanston in particular.

Find out some more where you want to live

Oh yeah…sorry if that wasn’t clear. Your 1x 52T setup would only work in the general Chicago vicinity…anythinig past ~Dekalb is gonna need a 2x, definitely!!

yeah, I think you’ll be fine in that regard. There are a number of really good local groups, both downtown and in the city itself.

Just in my area, there are 3 or 4 groups that I can ride with regularly…if anything, I’d say the number of groups available to ride with is increasing, since safety comes in numbers.

There are guys who ride year round…the LBS in my town sells stickers that say “365” and “182.5”, representing the number of days some guys ride outside. If you have a Fat Bike and good clothing (and the will), you can ride outside a lot. It simply is of no interest to me.

There is no sugar-coating the fact that winters here are tough…cold, lack of sun, snow that remains on the ground for months, etc. But plenty of people find ways to make it work…


Its fairly brutal in the winter but Chicago, and nearby Wisconsin have a good cycling culture, at least by US standards. There is a fairly prominent multi day race series in Chicago and another one in Milwaukee (90 miles north).

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I’ve been living on Chicago’s Northside for 25 years. And commuted to work (20 mile RT) for a number of them including 3 years where I commuted by bike every single day, including during the winter.

Winters are rough, but you can dress against that. The bigger problem is that the city of Chicago puts ridiculous amounts of salt on the roadways. (read this for a good explanation why no mayor will ever get caught not cleaning the streets). If you plan to ride year round, I’d suggest you get a winter bike, where rust, etc. is not that big of a concern.

As I get older (I’m 54 now) I still commute to work, but not from roughly Xmas to middle/late March. That to me is the deep winter period, where I will workout inside, and take advantage of the occasional mild day to ride outside.


LOL…something similar happened years ago in Denver.

The blizzard of 1982 has been blamed for the 1983 defeat of 15-year Denver Mayor Bill McNichols. The city was slow to clear main streets. Garbage trucks were deployed to pack side-street snow down to a navigable depth. Instead they created thin, dirty glaciers that lingered until just weeks before the May election.

The city basically became a massive skating rink for months!! :scream: :scream:

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Hey … there is a nicer way to say that :wink:

I haven’t read this entire thread yet, but I live in Chicago (north side of the city). The weather is challenging from Nov-March, but the rest of the year you can get outside on most days. You’ll become super smart about layering :slight_smile:

There is an enormous cycling community here … multiple teams, rides, groups, clubs from all different areas. If you are looking for a cycling community, you will definitely find one. The north suburbs are a verifiable cycling super-highway of group rides on the weekend, and the infrastructure for cycling is above average, in my opinion — I think it is better than New York and Los Angeles, from that perspective, but I have never lived in either place.

Things you won’t find:

– Hills
– Mountain biking (there is some, but not much)

Chicago-ian here… Where is this New Zealand? I can’t find it on my map.

  1. Is it safe? Yes. You probably have to go looking for trouble. There has been some “sport” robberies/carjacking in the city center, but these aren’t places you’ll likely ever be, though these are getting rare again. The dangerous places are well off the highway, and the locals will take one look at you can kindly give you direction out of the bad hoods rather than cause issues. Internationally, I think the US gets a bad wrap for crime for a few reasons, 1) being we have it , but 2) we typically have news reals of it which other countries news casts replay - I’ll go to Germany and see very local news on the air just because it was cheap for them to produce.
  2. Cycling - I think the better riding is in the North (Evanston to Lake Bluff) and Northwest (Buffalo Grove and further NW); along with the Des Plaines trail. We have light hills in the NW and by the Fox River, which you can work into a ride. It is very very flat - I ride 1x 52t on the road. MTB trails in abundance in WI, IN, and MI.
  3. Weather is shorts mid-May through late-Sept. My lower limit is 39f (4c) and can ride April 1 through - Late Nov. We get occasional outdoor days in the winter too. You probably don’t get all year cycling till you get down to Southern California, AZ, Texas, Florida, etc.
  4. Do people like living here? - Personally, I’ve worked a lot of places for extended periods of time, and the places I’d want to live otherwise is a very short list. I’d say it’s worth a try, but it’s not going to be all that different than living in NZ or Australia - probably a living abroad starter country. having worked for a number of very international firms, Chicago is generally well liked by singles and families. We don’t have many Kiwis or Austrians, but we probably have spots in town for everything else. Finding the right spot in town to live is key. If you don’t have kids, I’d have you be in a few select neighborhoods in the city or in Evanston. If you’ve got kids or want some rural space, then we’d need to talk.

Shoot me PM if you want to talk details.

  1. Hills - light hills would be an hour from the city center. Rolling hills, probably 2 hours.
  2. MTB - Trails, we’ve got some local ones, but good trail networks are 2+ hours away ( day trip - LaGrange WI, CAMBR trails, etc; lots of places in Western Mich 3-4hrs away; and quality in Southern Indiana and Northern Michigan - weekend trips)

I will give you the counter opinion as someone who lived in Chicago (in the city) for ~8 years:

  • The riding sucks / is non-existent if you expect to be able to get on your bike and just do a ride without driving somewhere first
  • The winter, if you aren’t used to it, is brutal
  • If you expect to stay in any type of shape, you will have to learn to ride indoors

I moved to Chicago from San Francisco, and my riding basically ended due to a combination of work + the riding was horrible, and I hate having to drive 1 - 2 hours to ride. My wife and I left Chicago after the snowpocalypse of 2011 - we just couldn’t deal with the weather anymore, and moved first to LA (awesome riding) and then back to San Francisco.

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Nine year inhabitant of Chicago here. I hate it. Run away. I’ve lived a lot of places in the US and my favorites would be New England (grew up in Connecticut), the mid Atlantic (lived in Maryland 30 miles north of DC) and Colorado (undergraduate degree in Ft. Collins), in that order. Also have spent time in North Carolina and central Florida, both of which are preferable. The road race scene in Chicago is anemic other than the weeks of Intellegentsia Cup and TOAD. Options for riding out of the city are sparse. Terrain is super flat. Weather sucks 5 months out of the year. Wish I could leave.


Thanks for all the great info, such a great community - although im not filled with confidence haha. 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.

I had in my mind I would be riding indoors 3 months which I can deal with, not sure about 5-6.

Our Tech scene and sourdough bread are also garbage! Where’s Chicago’s version of Marin county and Napa valley!
The skiing here is shit too. I bet when you lived in Breckenridge it was wayyy better. :slight_smile:

You’re comparing top of the heap to the rest of the world. Alt least we have housing and plenty of drinking water.

Not the best city in the Midwest IMO.

WTF. Opinions on Chicago were asked for, and I gave my honest opinion. Sorry you don’t like it, but your reaction is emblematic of the other thing we didn’t like about living in Chicago: it feels like a very angry city.

Look at the physical size of Chicago. Could be 30 minutes, could be hours. It’s a massive city. Need to know better where you end up looking.