Cycling in the City: An Overview of the Changing World Facing Bike Messengers & Couriers

By: Joanna McCall

In this blog, I will explain some fascinating aspects of individuals that work on their bikes. We have all seen them; maybe a Jimmy John’s employee has cut you off recently, maybe you have noticed the same person trekking downtown from your neighborhood with a sling bag and a radio every day, or maybe you have fond (or not so fond) memories of delivering local newspapers in high school. Whatever your relationship has been thus far, we are about to take a small dive into this world.

Let us start with messengers. These hard-working employees often work for downtown companies, making trips in and out of messenger centers all day, mainly on their bicycles. Notably, some of the “classic” forms of messengering—e.g., delivering paper documents – have shrunk due to the major advances in communicative technologies. Still, in large cities, many streets remain abuzz with bike messengers working weekdays 9-5. Short trips around downtown dominate this sector, but most companies also have “longboard riders” who travel greater distances and occasionally use vans as well. In Chicago, two of the most prominent messenger companies are 4 Star and US Messenger. If you want to take a deeper dive into some of the history here, look into Chicago’s own Joey Love and the X-Men from New York City. Pioneers in messengering undoubtedly deserve attention.

As the number of jobs in this more traditional mode declined, more courier work began to emerge. This work primarily consists of food delivery and various other cargo work. This strong emergence can be attributed to many circumstances, and it evolved into a model creating a substantial number of bicycle jobs in our cities. A notable presence here in Chicago at the beginning of this shift was Uptop. I currently work for Cut Cats Courier Collective, one pioneer of the courier “collective model”, which provides all workers enhanced responsibility to the company and to each other. This model allows the groups to contract clients they choose, either self-dispatch or be dispatched by another collective member, mediate the rates and conduct all matters of business within the company. Messenger and courier work can notoriously be dictated by some basement dispatcher and sustained by small checks, and this model works to break this mold in terms of jobs quality.

This collective approach is also being used in other cities. You can see Send It Courier in Toronto, Confluence Courier in Denver and Brick Road Courier in Orlando as a sample. Rain, shine or snow, these companies operate every day of the year. Only once in my four years as a courier have I been sent home early due to weather conditions: the Super Bowl blizzard three years ago. The only person capable of completing any deliveries that night had a cargo bike with a trash can full of chains on the front and his bike weighed just enough not to slide around.

Outside of this contracted model, you also have bicycle work in house for various restaurants. In some smaller cities, this is the primary source of employment on a bicycle. Restaurants such as Jimmy Johns and Potbelly come to mind. I worked at Jimmy Johns about five years ago. Their slogan, “freaky fast” is no hyperbole. I recall the fast paced environment in which a sandwich was required to be delivered within ten minutes of an order being placed. I also found many transient high school and college students came and went, eager to make a few bucks.

But one of the biggest stories of late is the surge in app-based bicycle workers employed by the likes of Ubereats, Grubhub, Postmates and Amazon. Cyclists working for these companies operate much the same way that Uber or Lyft drivers do; deciding their own hours at their convenience. This model of bicycle delivery varies in a few areas. First, the technology eliminates the role of the dispatcher. Secondly, the riders do not have a singular restaurant providing deliveries such as Jimmy Johns, or familiarity with contracted clients and their packaging. Finally, they have no structure allowing the deliverer to build “sets” and make money off of, say, four deliveries at a time. I suspect and hope that the efficiencies in these “gig economy” deliveries will grow as new strategies unfold, however they are no longer new and these models do not prioritize the worker.

When you’re working in food you’re also dependent on different ordering platforms to various degrees, depending on how you’ve built up your clientele. Some ordering platforms are already pushing delivery services in new directions. Recently, GrubHub acquired a platform called Eat24. It happens that Eat24 had hired many local courier services around the country as their exclusive delivery service. In the process, GrubHub has taken massive amounts of work from smaller companies. My bias, but also my experience, led me to applaud Eat24 for this business move: hiring a local company for their own expansion. GrubHub does not appear to value this sort of relationship the same way.

I would also like to make a prediction: American cities will soon see an influx of bicycle workers. It seems only a matter of time before the “mixed bag” of entities now operating in this sector will be replaced by a more integrated and less confusing structure. As Amazon and other monoliths consolidate—we are seeing pushback to cars taking “curb space” due to the surge in Lyft and Uber. This leads me to believe we will see bicycles play a larger role in the bigger strategic picture. Moreover, companies like one I work for are partnering with local restaurants or restaurant groups to test out new ordering platforms. Those findings could help improve the consumer experience and provide more quality jobs to bicyclists. Old-school messengering may continue to shrink, but food, cargo and other package delivery groups seemed poised for a takeoff. In the end, there could lead to a Darwinian struggle between companies like mine and various app-based startups. In fact, it’s already playing out to some degree today.

As we promote “active transportation” in cities struggling with issues such as congestion, curb-use and limited parking availability, it is encouraging to see bicyclists as part of the solution—and to see them continue to get paid for riding. Cities have every reason to pay attention to this small “enclave of employment” and work to provide bicyclists with a safe and efficient operating environment.

Check out our newest Chaddick Institute study on public transit and TNC use in Chicago

On Thursday, May 10th, the Chaddick Institute released our latest installment of our Policy Series. This report, titled “Uber Economics: Evaluating the Monetary and Nonmonetary Tradeoffs of TNC and Transit Service in Chicago, Illinois”, explores the ways in which transportation network companies like Uber and Lyft are used in contrast – and in conjunction – with public transit.

In addition to analyzing the estimated travel cost and times for over 600 trips in Chicago, we also highlight several exciting TNC-transit partnership programs throughout the country.

Head on over to our website here to check it out, and if you have access to PowerPoint, download our quick overview of possible synergies between TNCs and transit here.

Chicago’s ACTIVATE Events: The Loop in a Whole New Light

By: Elizabeth Balsavich

For many of the graduate students active with the Chaddick Institute, the city’s famous “Loop” district is their preferred place to work, recreate, and socialize.

When we think of the factors that make this area so inviting, we usually don’t think of cardboard boxes, dumpsters, narrow alleyways.  Yet the Chicago Loop Alliance has combined all three to make an interesting and memorable series of events called ACTIVATE.

I had the opportunity to check out the last ACTIVATE event of the year with a group from Chaddick.  “Simple, strange, chaotic, and eccentric” are all the words I’d use to describe the atmosphere. Being from a rural town in Michigan, I must admit I was a bit out of my element.  At one point, we were quite literally dancing next to a row of empty garbage bins!  Although I was a fish out of my pond, I almost instantly found an appreciation for why these types of events are all the rage in many major cities.

These event series turn alleys into creative spaces to exhibit the vast array of art that this city has to offer; they also bring together people to interact with this home-grown art face-to-face. The theme on this night was waste; hence, the dumpsters and cardboard boxes were everywhere.

Our group – all graduate students from the School of Public Service and Sustainable Urban Development programs– took advantage of the towers of cardboard boxes. With teamwork and creativity, we created a rather large transformer who loves to give free hugs! We amazed bystanders who even asked for a coveted photo-op with our giant cardboard creation. We study policies, public service, and urban planning, but we can harness our inner child and build things too!


Amidst the chaos and business of the city there is a rare and underappreciated beauty—people of all ethnicities, cultures, ages, orientations, and interests can come together in an alley and simply enjoy the oddity and excitement of socializing among strangers…and, well, dumpsters.  This event brought it back to its most beautiful state of simplicity.

What were some key takeaways?

  • Chicago has some impressively creative artists, not to mention some surprisingly clean alleys.
  • Somehow, the Chicago Loop Alliance was able to transform an ally – dumpsters and all – into a museum, a dance floor, a bar and a playground all in one.
  • Our School of Public Service students’ innovation was on full display, using cardboard boxes to build our own creation.

In the bigger picture, the event provided me new insights into how these events can give cities a new dimension.  Buildings can only be built so high and new parks can only achieve so much.  Who would have ever thought that an alley could be used as an art exhibit, a bar, and a creative space? I applaud CLA for thinking “out of the box”.

Cheers to the Chicago Loop Alliance for identifying and capitalizing on such hidden potential – check out their website to find out more, and keep an eye peeled for next summer’s events!

Can’t wait for next year!

-Liz