Outdoor training roads in Chicago

I’m looking for a good outdoor route within or near the city of Chicago that can sustain sweet spot or higher workouts. I’m just not aware of a long climb/safe & low traffic area that could support higher power numbers. Our Lakeshore path is just so busy, I worry about vo2 max, threshold, or sweet spot efforts when the path has walkers, rollerbladers, kids etc, and I would prefer not to ride 30-50 minutes just to get to a spot where I can then start a workout (time limited as most of us are, and I try to workout before kids wake up or after kids go to sleep). Thus most of my workouts are indoors, but as my motivation drops, I’m looking for ways to spice up the continued training and want to explore outdoor training.
Anyone have any spots to recommend in chicago?
Also, any chance TR could create a website or database of segments that are user generated ,where riders could select the state, city, and get a map based view of great areas to do outdoor training?

If you are downtown (and it sounds like it), it is going to be a struggle for you. A lot of city riders head north up into Evanston, etc and you can access good roods from there. I’m up in the northern burbs and even here I struggle with finding roads for long sweet spot intervals. The roads around Barrington tend to be where a lot of riders form this area head.

And there simply are no long climbs in the area…any where. Bull valley has a few short, steep ones, and Barrington Hills has some decent rollers, but overall, hills (and especially long ones) don’t exist.


Don’t train on the LFP. It’s just not worth it at speed. Too big of a risk with very little reward. If you need to go on rides there, go south past the museum campus.

For routes, Chicago doesn’t have hills, but it does have wind. Plan your rides into it.

If you can’t leave the city, there are a few other options. You can use estabilshed race courses and inner roads of parks during early morning. For example, the training crit loop at LaBagh woods, Lake front crit at montrose park or using the Humboldt park inner road. Furthest option would be Calumet park.

The other option is using the diagonals. You can get a pretty good pace on Ogden both south and north. Or you can use what was called The Knife when it was messenger race Milwaukee to Elston, Elston to Milwaukee.

Last option, if you are on a cx bike or gravel bike, you can set up a course in Humboldt or Montrose.

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The canal trail in Willow Springs is flat and goes all the way to Lemont. There is a branch off Kingery Highway that go to Palos Park

I know this probably isn’t as much help for OP, but I feel I must share a hidden gem location for outdoor intervals the NW suburbs if you live there. I use this loop for literally all my outdoor intervals, and so far, it has been perfect for everything: sweet spot, short shorts, Vo2 intervals, etc.

It’s essentially pan flat, with two intersections both of which you can turn right on at speed. It’s a business park, so early morning or after hours it is virtually empty, and on weekends, it is barren. It also has a dedicated bike lane the whole way around the loop on both sides of the roads which is welcome for the longer straights so cars can pass without issue. Only after hours issue is during hockey season with the ice rink at the southeast corner, but even then it’s still the best interval location I’ve found without making it out to Barrington Hills.

What the hell? No idea why it wouldn’t be visible for you. Tried making it in VeloViewer but it’s not showing up there either, so something’s broken with the segment, it seems. Here’s a pin drop in the middle of the loop on Google Maps.

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is it a private segment? Or maybe Strava servers are having a moment LOL

these work:


it kind of depends where you are in the city. Your best bet is to head in whatever direction that takes you out of the city in the least amount of time if you’re really trying to optimize for time.

otherwise if you’re on the north side of the city then what @Power13 has said will treat you well. I’d head north through evanston and head to fort sheridan. It’s pretty much always populated with cyclists and I think the drivers are more or less used to sharing these routes.

the reality is that we’re in the middle of a dense area in the third biggest city in the US, so getting away to long stretches of road where you can do long intervals is going to be incredibly difficult without having to travel to it. lean on trainerroad indoor workouts when time is short and head out for nice long rides when you’ve got the time

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Sheridan Rd. north of the B’hai temple up to Ft. Sheridan and back is a cycling super highway.

DO NOT try to train on the LFT unless it is Oct-Apr. I live on the north side of the city and has several routes that get me north in a reasonable manner - I’d check out Strava Global Heat maps. You will see the Sheridan Rd./Green Bay Rd. loop up north.

There are no hills to speak of in Chicago, truly. There are some secret steep climbs here and there, but nothing more than a 1/4 mile long. It’s the flatland, crits are king.

I love riding here, but don’t wrestle with the paths in the summer…use them as gateways to cleaner roads.

I’d be happy to help out further…I’m in Lincoln Square

Dude that thing about paths is so real. So many people ask me if I ride at Busse Woods and I just laugh at it now. Between the unsecured fishing lines, dogs on leashes, strollers and inattentive runners and rollerbladers, it’s a total minefield for a bicycle. Paths are not a destination, they’re a leg on the journey.

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Agreed…and as an added bonus, after a few hot laps around Fort Sheridan, you can head south just a bit and hit Tala Coffee for some of the best damn java in the city. Located in Highwood, about a mile from the Fort.

Get the blueberry donut. Trust me. :sunglasses:


Great tip. Always looking for great food/coffee stops. Will add this to my next trip up there. Thanks!


Lincoln Square! great. I live in roscoe village. I just created this in ridewithgps to that sheridan rd/green bay rd area and I combined it with a lake bluff route from evanston bike club. What do you think about the roads going to and from the Bahai temple area? It’s a 58 mile loop, which I can’t conceivably do in a 2 hr window before work, but if the route there and back is good, I can cut the loop short on weekdays.