As anyone who listens to the podcast likely knows, I don’t live in downtown Chicago. I spend time there occasionally, but not all that frequently. When I am there I take cabs when necessary, and the subway when it’s convenient, but almost never buses. I had been following Lisa Frame on Twitter for a while and she kept mentioning Sidecar. When I finally looked into it, I discovered it was one of these “ridesharing” (Lyft is another) services.


The idea is basically that drivers sign up to provide rides to people. These drivers have to meet certain criteria, including background checks, in order to be approved and put into the system. People looking for rides use a mobile app1 to sign up for the service and provide a phone number and credit card number that is used to provide some protection for the drivers.

When a person needs a ride they open up an app on their mobile phone, indicate their pick-up location and drop-off location, and wait for a driver to respond. Drivers in the area have the option of signing up to pick up that passenger. Once they do, the app notifies the user of who their driver is, their name, a picture of them, and a picture/description of their car. It also provides an ETA and shows their car on a map so you can see exactly how far away they are as they drive towards you. When the trip is over, the rider has the option to give the driver a donation (more on this shortly) directly through the app. A recommended value is provided based on the distance (I assume) of the trip.

Our Experience

Mrs. Hippo and I utilized this service twice over the weekend, and in particular hoping to compare it to the experience of taking cabs. The initial trip was from about Michigan and Wacker to Lincoln Park Zoo. There were about 5 drivers or so operating in Chicago at the moment (at least that is how many showed up on the map), we requested a ride and got a response from a young gentleman2 who was about 10 minutes or so away. It indicated to him that this was our first time and he called us to let us know where he was and when he would be there, which was a nice touch.

This is when I realized was one of the potential downsides to Sidecar. If we had taken a cab we would have gotten right in and been on our way. But in this case we had to wait about 10 minutes for him to get there. Of course, once you learn this, and the fact that you get a text when your car is close, you can plan ahead better and request the ride before you leave wherever you are.

The car he picked us up in was a nice, relatively new four door something. It was amazingly clean, and he had bottled water available as well. He was very friendly and we found out that he was a medical student. How many cab drivers can say that? The ride was safe and pleasant and felt much better than a cab. He was very nice to chat with and made the ride much more enjoyable than it would have been otherwise. The recommended donation was around $9–10, but with traffic I have no doubt that taking a cab would have been much more.

Our second experience came later that night. We took a cab to dinner and then decided to use Sidecar on the way back which would give us a great chance to compare the cost of the cab to the recommended donation Sidecar provides. This time we requested our ride before we got up from the table, and if it weren’t for the naked bike ride trapping us, the ride would have been there in just a couple of minutes. This time our drive was a woman in an SUV. She also had bottled water for us, and was just as pleasant as the first driver. She told us some more about what it was like to drive for the service, as well as the community that the driver have formed. Again, wonderful experience

The recommended donation for this ride was $6. The cab ride on the way there was $6.85 before tip. Now of course the recommended donation is just that, recommended and a donation. There is no rule that says you have to give that much, that little, or anything. Drivers rate riders though, and my guess is that riders who don’t chip in get passed over eventually. For us though, this was a better experience than riding in a cab, and even with just the recommended amount it was a couple of bucks cheaper.


After the ride concludes, you are asked to rate your driver (“No Complaints”, “It was exceptionally good” or “It was pretty bad”) and then pick what the best part of the experience was (“Great Car”, “Great Attitude”, “Safe and Efficient”). Both of our experiences were excellent, and as I said, cheaper than the cab ride covering the same route at the same time. It will definitely be my go-to for transportation in the city in the future.

I definitely recommend it to anyone who doesn’t like cabs or public transportation but also doesn’t want to drive anywhere. Be prepared to make a new friend and chat though. If you are just planning to be on your cell phone the whole time, this might not be for you. I also think it’s a bit better with a friend since it makes the chatting a bit easier.

  1. Both Android and iOS are supported []
  2. I probably could give his name, but I won’t just in case []