Two weeks ago, I ventured up to Chicago to try Uber for the first time. Uber, of course, is the personal driving service which allows you to use your mobile phone to request a private driver. It started in San Francisco a little over two years ago, and has since then made its way to the Windy City and various other locales.

Hearing nothing but positive things about the service, I was anxious to head to the nearest city with Uber availability. Fortunately, that city is Chicago, a place that I have grown to love over the past few years.

And as it turns out, Uber is an absolute perfect match for Chicago. Passengers love it, but what’s even more interesting is that the drivers themselves seem even more ecstatic about the rapidly growing service…

How it Works

By now, even if you’ve never used Uber, it’s quite possible that you already know how it works. Quite frankly, it’s become the darling service for tech bloggers, and for good reason. To use Uber, all you need is an iPhone or Android phone decked out with the official Uber app. The app is a free download from either the iOS App Store or the recently rebranded Google Play.

Once you have the app on your device, simply sign up for an account, link your credit card, and off you go. As a bonus, Uber credits new users with $10 that will help reduce your initial fare.

From there, all you need to do is open the app, and you will be presented with a map of your surroundings. This map shows your current location, along with any Uber cars that are in the area. Once you’re ready to ride, simply tap the Pick Up button, and the closest driver to you will receive a notification. Once the driver accepts your request, you’ll be notified both in the app and via text message.

Inside the app, you’re given a rough estimate as to how long it will take before the driver arrives at your current location. Once the driver arrives, you’ll receive another notification and text message. During the transaction both you and the driver are given the option to contact each other directly via a phone call. This proved to be instrumental on a few occasions where my exact location wasn’t readily apparent.

From there, everything continues to be a straightforward affair. If you’ve ever ridden in a Taxi, then you should know exactly what to expect. You tell the driver where you’re going, and they take you there. Then you get out of the car and say your goodbyes.

The main difference here is that no physical money ever exchanges hands. Everything is handled in-app. The credit card linked to your Uber account is charged and the amount of time/miles driven is calculated in-app. It all seems very precise and convenient. After all, we are a society that is relying less and less on physical tender, and more so on credit cards.

That, of course, is a very high-level overview of the service. Continue on if you want to learn more on how the service works in-depth, including some of the idiosyncrasies, and opportunities for improvement that I see for the service. Still, I think it’s fair to mention that I’m totally in love with Uber. Even with the few issues that I noticed, it is leaps and bounds above any existing Taxi service out there. Uber definitely has a hit on their hands, and frankly I can’t wait until it expands to other areas of the country and the world.


One of the primary reasons that Uber succeeds is due to the accountability it places on both drivers and passengers alike. Drivers have accountability in that once they accept a request, the app gives you their GPS location, name, license plate, contact info, etc. Not only that, but after the trip is over you can rate your driver on a 5-star scale, and even send private comments directly to Uber itself from within the app.

Drivers, on the other hand, can learn if a particular passenger is a disruptive passenger, or a good passenger via ratings of their own. With this in mind, both parties will generally do their utmost to provide a good passenger/driver experience.

Driver Personalities

All in all, I think it’s safe to claim that I had a varied experience when it came to dealing with different drivers. All of the drivers, though, were professional, and sung high praises for Uber. In fact, it was kind of shocking to find that every single driver I rode with was in a good mood, willing to talk, and verbally praised the service.

The attitudes of the drivers goes a long way on reducing stress for both parties. The accountability, coupled with the fact that no tips or physical tender is involved, makes for a much more pleasurable experience. The drivers know they are being taken care of from a monetary perspective, and passengers know they aren’t being taken for a walk with illegitimate fare prices, and tip demands.


My trip to Chicago was only a couple of week ago, but even since then, Uber has made some changes with their vehicle availability. You now have the option to request a Taxi, a black car, or an SUV from within the app. It’s nice to have the choice, and it means that there’s always a vehicle available to you whether you want to spend a little, or spend a bit extra.

I found it very convenient to be able to take a black car out for drinks in the evening, and then turn around and use the same service the next morning to take a quick Taxi trip to visit a friend.

Combined I was able to ride in a Ford Expedition, Lincoln Town Car, a regular Taxi, and a Cadillac Escalade with nice shiny rims. The Escalade was perfect for my 11 PM drink date at Chicago’s Signature Lounge.

Cellular Service, or lack thereof

When it comes to Uber, I only have two complaints (really only once complaint, since the other is outside of their control). My main issue stemmed from the extremely spotty (downright embarrassing) cellular service that AT&T provides in Chicago. There were several times during my trip that I just couldn’t complete a driver request due to flaky cellular service from AT&T.

The lack of decent cell coverage from AT&T is in no way Uber’s fault, but it’s something that has to be noted. Without the necessary Internet connection, you can’t use the service.

In fact, I noticed that all of the iPhones mounted on the dashes of Uber cars were using Verizon as a cellular provider. I’m sure Uber is already well aware of the terrible AT&T service in the area, and hence, decked out their drivers with Verizon iPhones instead.


I don’t have a problem with Uber’s pricing, in fact I found it to be totally reasonable. With the addition of SUV’s, there’s plenty of selection to go around for more price ranges. The only issue I have with pricing has to due with estimating the total cost of a fare. It would be nice if there was a better way to tell how much a fare might cost in the end, using estimates, traffic indicators, etc.

Interestingly enough, Uber has updated their app since I last used it; they now include a page that gives users a better idea of what they can expect from a pricing standpoint. While it isn’t perfect, it’s a definite move in the right direction.

Uber does an okay job with trying to explain their pricing mechanics on their website, but they need a better way of implementing this dynamically within the app. Frequent Uber users will likely have the pricing estimates down much better.  But since I was an Uber newb, I found this to be a challenge.

The Bottom Line

I could literally write another 1,300 words telling you about Uber, but the bottom line is this: You owe it to yourself to try it if you visit a city where Uber offers its services. They give you a $10 credit to get your started, which is enough to cover a decent percentage of your average fare.

I’m a firm believer that this is the future of local short-distance travel for those wishing to avoid mass public transit. I have to say that I headed into this experience with high expectations, and I walked away with an experience that far-exceeded them.

Disclaimer: Uber provided me with a $50 credit to get me started on this walkthrough, but all of the other charges you see above, along with the total cost of my trip, came out of my own pocket.

  • Y Actually thought I’m gonna read the whole thing? LOL

  • Verizon’s coverage is much better than AT&T’s coverage here in Chicago.

    My two cents on Uber: It’s mostly good, but there are some gaps. Approximately a third of the time I’ve tried to get a car the estimated time of arrival of the car jumps significantly after I push the order button. Like, car is 10 minutes away? OK. Then, click on order, and now the car is 23 minutes away. WTF? I’ve actually also had a couple of whiny, not really snotty, but whiny driver experiences where one guy was flipped out that I didn’t answer his call when he arrived (I tried, but signal dropped, then I called him back and couldn’t get through to him), and my wife has actually had at least one driver experience where the guy just wouldn’t stop talking no matter what. A couple times the driver has been concerned that they haven’t been able to immediately find me when they arrive (calm down, I’m coming right out, I didn’t know you were here yet). These aren’t deal killers but they’re not resulting in us having an optimal experience, either. Pardon my privilege, but Uber has my name and credit card on file, if I really disappear without getting into the car, I’m assuming somebody still gets paid.
    Uber makes more sense in SF; smaller, more dense city. Indeed, I found it very handy when I’ve been in SF for business. But we’re pretty spread out here in Chicago. I live on the far north side and Uber cars aren’t usually that close to me. Sometimes I’ve been dragging cars up to us from 20 minutes south. I dunno how the drivers feel about that exactly. I assume Uber wants us to still order so it can help drive future demand to put the cars closer to the customers.

  • Fun fact: Uber provides its taxi drivers with free iPhones (data plan only) on Verizon’s network here in Chicago. Not AT&T. I wonder why…

    • ReanimationXP

      How the hell do you get data plan only!?

    • Tim

      The phones cost drivers 10 dollars a week plus a weekly data charge.

  • As you said Jeff, this is definitely worth a try. Next time I get into the available cities I will do so.

  • Robert Goldberg

    Great article and video review Jeff! Amazing job!!

  • hkpuipui99

    Would be nice if you included a promo code 😉

    • JaeM1llz

      Promo code for a free app?

      • Hahahaahah some still can’t afford the free ones. Better go pirate it.

  • JEff how u gonna fly to Chicago when u live in Chicago?

    • JEff doesn’t live in CHI

      • Lol oh well his accent sounds like Chicago and coulda sworn I heard him say he lived in Chicago maybe it was an older post.

  • Moe

    This is my first comment on this blog even though I always follow idownloadblog and dev team blog for latest info however leavening comment was the hardest because I never left one before the truth I never know how until now still I don’t know how to leave comment on the dev team blog can any one
    Let me know ho to do so thanks in advance for ur help

    • Anyone understand what he said?

      • If I understand correctly, He wants to leave comments on dev team blog. He needs someone to help him doing that.

    • ReanimationXP

      If you’re unable to compose a sentence properly, you really have no business being on a jailbreaking site.

      You are the weakest link, goodbye!

  • Great review. I’m a big Uber fan too. Did you have phone coverage with AT&T (as opposed to data coverage). You can text a request to Uber instead of using the app.

    My experience with them was similarly great. Each expansion of service and coverage is a welcome one!

    • You know, I didn’t even think about that, but I think I was DOA anyway, because I couldn’t even make a phone call.

      • Yes, it’s not often that you can get phone service and not data but SMS sometimes works when nothing else will.

  • Nice Idea.. It would be great if it is done here in Saudi Arabia.. The carrier coverage will not be problem and it will save a lot of time.

    Gonna think about it.. It was never done here before.

  • Sean

    Great stuff. In Amsterdam we have some similar taxi apps like Taxi Amsterdam & Cabster which work great. But I like the look of Uber a lot better.
    I’m also a big user of the Car2Go service over here. Just a big fan of “next gen” mobility overall. So I’m quit curious about what the future will bring us..

  • WaterTrooper

    I wonder how much they pay their taxi drivers it might be a interesting company to work for.

  • Great review Jeff (5*****) from me

  • It is great…i am lovin it!

  • Really solid review Jeff. Looking forward to trying this out in San Fran during JailbreakCon 🙂

  • Tall Consultant

    I have used Uber in both Chicago and SF. Chicago has a problem with getting the accuracy of the time and location. Someone stole my cab and I was charged for it. Thankfully Uber promptly fixed that, but in SF, I was charged twice for a ride from SFO to the city, and it has taken over four days and it is still not resolved. I have taken it up with AMEX and Uber, but Uber is very slow to respond here in SF. Sad,

  • scott razr

    I drove for uber for about a month during Christmas New Years. They hired thousands and quite unceremoniously gave me the boot because of a 4.6 overall rating. This is 92%. Most would consider it an “A”. Warning: if you are cheap with the ratings and give less than 5 stars because your ride wasn’t perfect, or the driver forgot to open your door, or give you a bottled water then you may be effectively signing them out of a job.
    I rated every passenger 5 stars. Whether or not they were wonderful, talked to me, didn’t talk, or talked too much.
    I am not angry with the company as the pay was fine and they were very businesslike. I do think they hired thousands for a busy time in L.A. and then layed off most after the holidays.

  • Verizon has a “hot spot” service for $30/mo which is a high fee unless you live somewhere where you have a lot of wireless connect issues. With the hot spot, you ARE the internet connection and I’ve always had success with using it as a last option. It’s saved me many times!

  • Jason

    Having AT&T is the equivalent of freeze drying a dog turd and using that as a phone.

  • FN786

    Great experience in Uber. Save $20 on your first ride. PROMOTION CODE: 19V7C

  • Wolfe A

    Yea, well, unfortunately the country is full of non-politicals who think watching the Kardashians on TV is interesting and believe and repost everything they read on Facebook. If we aren’t careful we could quite easily end up with Trump, which means we better start learning Chinese because they’ll be our rulers when he defaults on our loans.