Driver’s Tollbooth

This page is dedicated to rideshare drivers in the Chicago market


Q: MDW and ORD rideshare drop-offs, are they worth it?

A: No. In a vacuum, drop-offs to both MDW and ORD are lucrative.  But you should add in the time it takes you to begin your next ride and the pay per minute drops substantially. In a vacuum, a ride to either MDW or ORD from downtown Chicago will often net better that $20.00, for less than an hour of driving.

I have spoken to drivers that prefer airport rides as they either desire the safety of driving a business traveler (versus a drunken bar patron) or they live near the airport.

Neither airport is adjacent to any reasonable population density, and therefore the areas surrounding airport areas lack the requisite demand to make rideshare driving lucrative.

Q: What about waiting in the MDW or ORD airport queues?

A: No. It does not work for me.  I have waited at MDW for over 30 minutes only to get a nearby ride that netted me less than $10.00, and I have waited at ORD for over an hour only to leave frustrated without a ride.

The only time that I enter the airport queue area these days is to utilize the port-o-potties.

Recently I had an ORD dropoff, then I was immediately pinged for a pickup.  Against my better judgement, I accepted, and within 10 minutes had my passenger in my vehicle.  Unfortunately for me, he was going to South Barrington- which was at least a 30 minute drive that took me legitimately 45 minutes from civilization, reasonable population density, and therefore, rideshare demand.  After calculations, I netted less than $20.00 per hour on these two (2) rides and put many unnecessary deadhead miles on my car.

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Q: What about leaving MDW and ORD after a dropoff for a ping?

Midway (MDW) lacks the requisite population density to make rideshare driving lucrative.  Certainly there are times during the day when the surrounding neighborhood and suburbs can work in a driver’s favor.  I actively avoid suburban rides and driving 15-30 minutes through the neighborhoods on local streets to get to a neighborhood with requisite rideshare demand. Driving without a rider or a ping does not appeal to my sensibilities.

O’Hare (ORD) also lacks the requisite population density to make rideshare driving lucrative. Early nights and weekends a driver can net a ping in nearby Rosemont. But, Rosemont is a city of 4,200 people largely hidden within gated communities. Rosemont has tourist attractions like an outlet mall, a casino, multitude of hotels, a convention center, and the All-State Arena.  These attractions, when active, will provide pings to rideshare drivers.

Perhaps you, as an experienced driver, have a reasonable strategy for a ping in the Golden Corridor after your ORD drop-off? Please comment below!

Q: What are the best times to accept MDW and ORD rides?

This question is better answered with the worst times.  The worst times to drive to MDW and ORD are Chicago’s recognized rush hours with a few additional hours added at both ends.

5:40am-10:00am; 2:00pm-8:00pm: Avoid airport rides during these times. The morning hours I am absolutely sure of, but the afternoon hours I have less personal experience. Of course there are exceptions- I completed three (3) dropoffs to ORD on Memorial Day 2017 before 7:30am, but traffic was negligible and caused me zero delay.

The idea is that you’ll spend 45 minutes in your vehicle in bumper-to-bumper traffic for a $20.00 ride unable to get your next ping for a minimum of 30 minutes after your airport dropoff.

There simply is not a strategy that I have discovered that makes an airport ride lucrative for a Chicago driver.  Surge and Prime Time will increase earnings, but often at the sacrifice of more of your time.  Go ahead, you can have the 1.5x Uber surge or 50% Lyft prime time at 7:45am, because I don’t want anything to do with it!

Uber Quest Strategy in the Chicago Market

Uber generally offers two (2) quests per week. 1. Monday through Thursday; and 2. the weekend. Since I drive both Uber and Lyft and absolutely prefer Lyft in nearly all circumstances (as of this writing in June 2017), this is a secondary strategy for me personally.

The quests are within reach for a part-time driver.  The rideshareguy stated that different drivers receive different quests during the same week, so its probably a test tube for Uber to see what compensation level motivates us to drive for them as drivers.


Routinely, I will not bother with a quest unless the pay is at least 2x the ride quest. For example we might see these 2x quests:

  • Complete 15 rides, receive $30
  • Complete 18 rides, receive $40
  • Complete 20 rides, receive $40
  • Complete 25 rides, receive $60

 More often I see these types of quests:

  • Complete 15 rides, receive $20
  • Complete 18 rides, receive $25
  • Complete 20 rides, receive $25
  • Complete 25 rides, receive $35

Last week I nailed this one:

  • Complete 15 rides, receive $60

This week I will be hitting this one:

  • Complete 25 rides, receive $60

Since I am shooting for the Lyft double-bonus > 75 rides of which, 35 are “peak hour”. I am seeking a low or manageable number of rides for a high bonus through Uber.  Remember that we cannot see a Uber rider’s rating in the Chicago market (as of this writing June 2017), so that appears to be the trade-off for Quest (even though Quest existed when we could view rider ratings).

There are second level bonuses for Uber rides and I have been unimpressed with those bonus payments.  They simply do not compare to Lyft.  That said, if you are Uber-only and you get close to the second level bonus, you should go for it!

Lyft driving strategy

To receive Lyft’s double-bonus, a driver currently needs to hit 75 rides.  35 of the 75 must be “peak hour” rides.  The times of peak hour rides have evolved slightly, but are basically this: 1. morning rush, 2. evening rush, 3. Friday drinking times, 4. Saturday evening eating times and Saturday evening drinking times.

My driving average is between 2.25 and 3.25 Lyft rides per hour, over any given week. We do get the occasional 6-ride hour and sometimes we don’t start a ride during a given hour (see airport rides above).


I do my best to avoid all suburban rides as the suburbs have low population density, don’t hit the correct rideshare demographic, and there is little demand compared to many Chicago neighborhoods.  Anytime I get stuck in the suburbs I turn on the destination filter, but it hardly matters as people are not interested in leaving for downtown Chicago at 1:00am from Naperville.

On Monday, Tuesday, and Wednesday I drive from 5:00am-10:00am to acquire peak rides and ‘run up the score’ (get a decent number of rides on the weekdays to make the weekend less about accumulating rides, and more about enjoying conversation). On Thursday, Friday, and Saturday, I drive at night through 3:00am.  I love conversations with my drunken passengers and look forward to the social experiences!

Through the week I drive a gas-sipping classic Lyft/ UberX eligible vehicle with five (5) total seats. On Saturday I drive a gas-guzzling “Plus”/”UberXL” eligible vehicle with seven (7) total seats.  I have found that there is not enough demand to drive the “Plus”/”UberXL” on any day but Saturday. At the time of this writing “Plus”/”UberXL” pays about 1.5x as much as classic Lyft and UberX.


Unfortunately, Lyft does not offer the ability to accept only “Plus” rides when driving a “Plus” eligible vehicle. I get classic Lyft and Line requests sprinkled into my Saturday shift. Uber does offer the ability to only receive XL requests, and there is plenty of demand in Chicago proper to stay busy through the night. As any driver knows the stereotypical demanding Uber Pool rider is one of the most detested rideshare riders.

Lyft appears to have the same heat map for its “Plus” rides as it has for Line/ classic rides. Uber has a completely different heat map for “UberXL” and Pool/ UberX rides and I view this as an Uber advantage when driving higher capacity vehicles.

I just dropped off the passenger, do I drive or stay put?

If you are in the suburbs, leave immediately! Put the destination filter on and hope for the best.

If you are at the airport, you just had 20-60 minutes to think about your strategy while inspecting the traffic congestion in the opposite direction. Time to deploy your ad-hoc strategy!

If you are in a high demand Chicago neighborhood, I would find a parking spot and stay put. If there is no ping in 10-15 minutes I would reassess my options and stage my vehicle in a different area.  While I am waiting for a ping I will give a cursory review of the heatmap to determine if there is a nearby surge or prime time. I try to stay just outside the surge and prime time areas as additional vehicles reduce the surge and prime time multipliers.  If I just dropped someone off in the middle of a 350% prime time, I hang out past when the prime time has completely dissipated.

If its the middle of the night, only personal and professional experience will tell you which neighborhoods have high demand.

If its the morning and you just dropped off a Loop office worker, what do you do next? Get out of the Loop! Unless you want to spend the next 1.5 hours regretting your acceptance to go to a hotel for an ORD/MDW airport ride.

Is Navy Pier of McCormick Place worth the hassle?

Right now Navy Pier is on my nice list.  I always call Navy Pier pickups as passengers have little to no idea where they need to be for the pickup. They are typically tourists from out of town and I can’t blame them for not knowing.

McCormick Place dropoffs are seamless. I haven’t performed enough pickups there to provide a well-studied answer.

Special Events, are they worth the hassle?

Special events have rolling street closures that are determined by the Chicago Police Department in real time that your riders and Waze drivers are generally unaware of. Beware of anything letting out at the United Center, regardless of the prime time/ surge. You will think rolling street closures are manageable until the traffic control aides and ticket writers start yelling at you and writing tickets.

Drop-off for a Bears game at Soldier Field? No thanks, get another driver.  I would rather not net a $6.60 ride for 25 minutes of my time. Get an inexperienced driver, they love to sit in traffic and study how slow their vehicle moves compared to the destination arrival time!

Communicating with tourists on rolling street closures, addresses, or cross-streets is fruitless. Should you accept a ride with rolling street closures, and the tourists don’t know the area, cancel immediately.  Allow someone else to drive around for 20 minutes trying to secure a pickup location with tourists.


If I am driving to a ping and I encounter a street closure not identified on Waze, I call the rider immediately, hear what they have to say, and generally play stupid.  Afterall, I just drove 5 minutes to them, they can traverse the final block and a half to get to me. Driving around in an unfamiliar neighborhood with a myriad of one-way streets and block party closures, while searching for a rider is a losing proposition. Cancel this ride if this is what the rider expects of you as the driver.

Obviously, you need to determine your own rules for making rideshare driving lucrative. For me, many of the above rules become flexible with higher degrees of prime time / surge pricing. The overriding factor with me is racing to 75 Lyft rides, which I have hit in under 25 hours, but usually takes about 27 hours.