Why Direct Biking Streets Aren’t Always the Safest or Most Enjoyable Option

Side-street itineraries are great for low-stress riding -- especially with kids

Gin Kilgore rides with her son Miguel, now 11. Photo: Michael Burton
Gin Kilgore rides with her son Miguel, now 11. Photo: Michael Burton

It’s fitting that John Greenfield’s Mellow Chicago Bike Map project has helped to rekindle my love of cycling in Chicago. John and I met 20 years ago at some kind of bicycle planning event, back when the Chicago Department of Transportation’s bike map was more aspirational than boastful. The few existing bike lanes were connected by orange “recommended routes” that were deemed reasonably good places to pedal.

I had just started commuting on a little mountain bike, because that’s how many Chicagoans rolled in the late 1990s, and was dutifully following the orange lines, including taking Milwaukee Avenue to ride downtown from the Near Northwest Side. The trips were functional but not particularly fun. At the time, John suggested taking Wood south to Hubbard as a less stressful alternative. Although losing the diagonal added a little distance, it made the trip much more relaxing.

Eastbound route from Logan Square to Bucktown via Lyndale. Image: The Mellow Chicago Bike Map
Eastbound route from Logan Square to Bucktown via Lyndale. Image: The Mellow Chicago Bike Map

Late night rides with new friends from Chicago Critical Mass expanded my mental map of low-stress streets.I learned that you can shortcut from Logan Square to Bucktown and the Webster bridge over the Chicago River by crossing the Goethe Elementary playground and continuing east on Lyndale. Barry Avenue is a great westbound alternative to busy Belmont. Leland is a more peaceful option than Lawrence for heading east from the river.

But my terrible sense of direction and tendency to space out has always made it hard to fully recreate these routes on my own. My guides were master pinball players, who would bounce south on Ravenswood, west on Grace, south on Wolcott, west on Melrose, and south again on Leavitt to the Diversey river crossing. I always found myself gravitating back to Damen, which is not the worst street to ride on (it was probably one of Chicago’s recommended routes, and one of the first streets to get bike lanes.) But, with plenty of car traffic, it’s not all that pleasant either.

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Some of the more complicated stealth routes may require writing down directions. Photo: Gin Kilgore

Fast forward a few life stages and I’m now riding with my 11-year-old son. A few weeks ago, after a harrowing “Must keep moving! Must stay in line!” ride up Racine to an appointment at Illinois Masonic Hospital Lakeview, I sent John a rant about how I sometimes envy the way families who drive are able to have conversations and not worry about what could possibly go wrong while biking with a kid (even a fast, traffic-savvy kid) sandwiched between impatient motor vehicle drivers and parked cars. Although I know many residential street routes that allow for a more tranquil, shady, and side-by-side ride (yes, we yield to car traffic behind us—Miguel is all about yelling “car back!” to warn about approaching motorists), I still sometimes get stumped on longer rides.

A low-stress route fro the Bloomingdale Trail to Illinois Masonic Hospital. Image: Google Maps
A relatively low-stress route from the Bloomingdale Trail to Illinois Masonic Hospital. Image: Google Maps

In this case we needed a lower-stress connection from the east end of the Bloomingdale Trail at Marshfield to the hospital at Wellington/Sheffield. Instead of taking Cortland to Racine to Wellington to get there, John suggested a stair-stepping northbound route of Cortland/Racine/Armitage/Seminary/Wrightwood/Mildred. Seminary is one-way northbound south of Fullerton, but a quick jog west to Clinton via the DePaul campus solves that problem for the southbound trip. Game changer!

I am now more motivated to scrutinize maps before taking a longer trip to find ways around challenging intersections and other barriers that can make these calmer routes tricky. I recently discovered Avondale (a relatively low-traffic frontage road that parallels the west side of the Kennedy Expressway) serves as an awesome alternative to hectic Milwaukee and Elston between Irving Park and Addison. A couple blocks south of Addison, you can bear right (make sure you don’t continue straight onto the access ramp for the highway!) to get on Central Park, a good route to Logan Square.

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The Avondale route. Image: Google Maps

The other day we used a wiggling side street alternative to Kimball to get from our home in Logan Square, across the Kennedy, to Addison/Albany, at which point Miguel led us north on Albany to connect with the North Shore Channel Trail near Lawrence and Sacramento. That was the starting point of a Father’s Day Ride organized by Kevin Womac, the owner of Logan Square’s Boulevard Bikes (a Streetsblog Chicago sponsor.) We spent very little time on main streets. It was already hot and humid, but the shade and ease made the miles click pleasantly by – it almost felt like we weren’t exerting any effort.

On the way home, we wound up high-tailing it southeast Milwaukee back to Logan Square to make a movie showing. It might have been the direct route, but it was hot and stressful. In retrospect wish I had just pulled over, taken a few minutes to come up with a better plan, and found us some shade. In fact, the mellow side-street routes are sometimes just as fast or faster than direct ones because you don’t get stuck at monster intersections.

  • Bobo Chimpan

    I agree that Barry is better than Belmont heading west… and I still hate going west on Barry. It’s really not wide enough to be a two-way street (though I realize if it were one-way it would only go east, making it useless to me) and some blocks are more pothole than pavement!

  • johnaustingreenfield

    Roscoe, two blocks north of Belmont, is another good westbound alternative.

  • roy999

    Gin, I am John’s old decrepit dad. Interesting to see your son. Last time I saw him he was a little baby. I remember five or six years ago John and I were biking through some of the quiet Chicago streets and he talked about doing the mellow bike map. I was pleased to see that he did it and did a nice job. I still bike, i’m fairly flat areas I still use a highbred. But most of the time around State College Pennsylvania which is very hilly I have switched to a electric assist bike.

  • Gin Kilgore

    aw, thanks! I need to share a newer picture of him. He recently inherited my old “racing” bike and is almost as tall as I am and definitely is much faster.

  • Tooscrapps

    Everyone loves a low-stress route, but the reality is that often times those routes lack a key bridge or viaduct. Many side streets dead end, turn into one ways, or lack a traffic control at a busy street.

    I’ll take a good side street short-cut where I can get them, but if I’m trying to get somewhere (especially over 3-4 miles) fast, I’m relegated to the heavily traffic corridors.

  • what_eva

    I think they’re talking east of the river where Barry is mostly one-way westbound. From Halsted/Clark to the river there are a few short sections of two-way, otherwise all one-way westbound.

  • Gin Kilgore

    I agree, which is why I have enjoyed this project and am paying more attention to navigating those pain points. Some crossings are less horrible than others and I’ve become more willing to add a few mins or blocks to use them. The Avondale example is the article is a good example. The highway crossing at keeler is much calmer than the busier arterials. I’m trying to burn these locations and the little jogs sometimes needed to access them into my brain. Otherwise I become the sad pinball plunging down those main drags instead of zig zagging home.

  • johnaustingreenfield

    Correct, Barry is one-way westbound essentially from Clark to the river. It’s not really a practical, contiguous bike route west of the river until after Cicero.

  • johnaustingreenfield

    Many of the routes on the Mellow Map parallel bikeable main streets and return to them at “pinch points” like river, rail, and expresssway crossings, and then return to the side streets after that. If you’re doing a trip that requires making right angles across the grid even if you take main streets, stair-stepping on residential streets, such as the route shown from the Bloomingdale Trail to Illinois Masonic, doesn’t necessarily take longer than sticking retail streets. But, sure, in some cases it’s a question of choosing comfort or speed.

  • Anne A

    I have vivid memories of learning to ride the hills in and around State College during my time there back in the 1980s. It was quite an adjustment after growing up riding in Chicago’s flat terrain.

  • Anne A

    Gin – Your description of starting with Milwaukee and branching out reminded me of my own early experiments in bike commuting from Rogers Park to the Loop when I first moved back here. I started with Clark St. – direct but quite unpleasant at times, and sometimes dangerous. I tried some less direct routes and came up with a bunch of useful combinations. One of my favorite discoveries was a routing that included pleasant moments with a crossing guard and kids by an Uptown school (when school was in session).

  • Anne A

    Google Maps satellite view is a very useful tool for figuring out if a quieter street on your potential route has safe crossings at major streets. The secret – looking for stop bars on the pavement. When you go to the link below, look for the wide bars before the crosswalks on Ashland. Wherever you see that on a major street, it means that street has either stop signs or stop lights, so you should be able to cross on the side street without waiting an eternity or risking your life.


  • Tooscrapps

    Agreed. It’s saying something that for cyclists to access safe routes, you have to burn the tricks into memory, rather that being intuitive. For instance, I hear over and over from friends and colleagues that they are hesitant to bike to work because they don’t know a safe or enjoyable route.

    Motorist aren’t subject to such inconveniences.

  • johnaustingreenfield

    Great tip Anne. For the Mellow Map, I found stoplight locations by using this CDOT map — click “signals” in the sidebar. http://webapps1.cityofchicago.org/traffic/ https://uploads.disquscdn.com/images/44b4ee40705adac1a3bb5c458eed849dc0570886ae93ec2c1d04cad5d49748e6.png

  • johnaustingreenfield

    Thanks Dad. Folks, you can see where I get my proofreading skills from! Seriously, though, my father is not so decrepit — he still rides a bike just about every day at age 82.

    “Death may have no master, but the bicycle is, most emphatically, not its servant.” – James E. Starts

  • Carter O’Brien

    Yeah, I often take Barry to Clybourn from Lincoln (Lakefront>Stockton via North Ave tunnel and Lincoln Park> Dickens>Lincoln), but as you note, it is a really crummy street, physically speaking. We reeeeeeeeeally need a bike-ped bridge over the Chicago River somewhere between Diversey & Belmont, it’s unfortunate the new fancy elevated trail isn’t going to do anything to improve connectivity challenges for Avondale.

  • ChicagoCyclist

    That’s a splendid quote!

  • ChicagoCyclist

    In addition to needing — or at least strongly desiring — a signalized intersection to cross (or sometimes even to left turn onto) larger and/or higher-volume and/or higher-speed streets, another consideration (or let’s say, secret tip) when choosing/looking for fairly direct low-stress (i.e. low volume, low speed, shaded) streets is that, while in Chicago quite a few such streets are one-way, they can nevertheless be easily, safely (though technically illegally) ridden “counter-flow.” While I am not recommending this, I am … just saying. These situations are what I call “natural neighborhood greenways,” which in Chicago often feature counter-flow bike lanes. Anyone riding counter-flow should be aware that vehicles at cross streets, driveways, alleys, and even those pulling out of parallel on-street parking spots may not be — probably are not — looking for or expecting cyclists to be coming from the ‘wrong’ direction. Caveat birota!

  • JacobEPeters

    This is why I love the Chicago Bike Buddies program https://chicagobikebuddies.com/about-us/ & recommend them to every new resident of the city, or friend who is picking up cycling. Once you figure out the low stress routes to get you from your house & office to your most common destinations then cycling in the city becomes a lot less stressful.

    That being said, we need more safety improvements at intersections with bike lanes because there are quite a few intersections that are unavoidable for getting across the river, under a highway, or anything else that disrupts the grid.

  • ChicagoCyclist

    John Greenfield — and others interested in this effort — you may be already be aware of this similar mapping initiative in Denver: https://www.bikestreets.com/ Pretty nice website, eh? The person who thought this up is named Avi.

  • Bobo Chimpan

    Ah, OK… east of the river I use Roscoe to avoid Belmont, or just take Belmont. It’s really only between Kedzie and Kimball that Belmont scares me, and even then only westbound… but I’ll go a mile out of my way to avoid going west on that one block


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