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The Chicago Drivers' Guide to Rideshare Street Smarts: The Lake's Edge (Near South Side)

James has driven rideshare through all 77 Chicago neighborhoods.

Shedd Aquarium with city in background

Shedd Aquarium with city in background

Cashing In on Coastlines

The ten best rideshare driving locales include seven with Lake Michigan beach fronts. The remaining three rub elbows with Chicago River banks at some point. Near South Side shares a coastline with both the Chicago River and Lake Michigan. Its city center location flanked by Chicago’s premier waters draw residents, visitors, and their rideshare demand.

Skyline view from the Shedd Aquarium

Skyline view from the Shedd Aquarium

Da Chicaguh Drive Demand Directory



Rider(s) who leave from or return to their homes

Pick up from "Theatres at Roosevelt," drop off at house

Resident rider(s) can also be commuter, consumer or guest depending on pick-up drop-off spots


Rider(s) who go to and depart from a place using public transit options

Employee going to work who takes a rideshare to a train station

Commuters are often residents, sometimes consumer and on occasion guest


Riders who go to and/or depart from a location they visit to engage in a chosen activity

A car load taken to see Dave Matthews Band at Northerly Island’s Huntington Pavilion

Consumers are often but not always guest


Riders who temporarily leave, lodge, or linger in Chicagoland

Tourist and virtually all hotel/motel and airport trips

Guest are often consumers of the area's featured attractions

Near South’s central city proximity gives rise to direct home-to-work rideshare trips.

Near South’s central city proximity gives rise to direct home-to-work rideshare trips.

Neighborhoods that provide two sources of extraordinary demand will make you money. Chicago’s Near South Side boasts three explosive beyond extraordinary sources of demand. Resident, consumer, and guest requests here are abundant.


Dearborn Park is a quietly ornate district evenly split between the Loop and Near South Side. Although it’s small (estimated one mile north/south ½ mile east/west), its rideshare demand is large. Dearborn’s State Street presence produces prodigious trip totals.

Near South also includes a residential area bordered by Roosevelt Road, 18th Street, and Michigan Ave to the north, south, and west. The north half of the historic Prairie District is within this region.

This expanse has several double-digit dose trip-producing residences in less than one square mile of city space. This has led me to numerous surcharged evening peak hour drop-off trips. Near South’s small area housing package engenders big dollar rideshare driving revenue.


Near South’s central city proximity gives rise to direct home-to-work rideshare trips. River North and the Loop, areas with a substantial business presence, are nearby. The cost difference between taking public transportation or directly to work “via” a lyft in an Uber may not matter to Near South Siders regardless of a rideshare tax. (puns intended) Taking residents from one super surcharged zone to another is a good source of morning business even at short distances.

Chicago used to have a lakefront airport. Now its Northerly Island, an urban nirvana.

Chicago used to have a lakefront airport. Now its Northerly Island, an urban nirvana.


The Museum Campus

Near South Side venues offer the most concentrated collection of cultural and crowd-pleasing settings in all of Chicago. The museum campus offers a tremendous trio of iconic sites within ¼ mile of one another: the Shedd Aquarium, Field Museum of Natural History, and Adler Planetarium.

The Shedd and Field Museum each greet nearly two million annual visitors.[1] The planetarium has welcomed over half a million stargazers per annum to its site in recent years.[2] Their attendance enables consumer/guest trips practically all day long, every day, and throughout the whole year. The campus, along with Navy Pier and fellow Near South neighbor McCormick Place, has provided me with the most instances of passenger drop-offs immediately followed by new pickup requests.

The Stadium

The Chicago Bears (by ESPN figures) hosted nearly half a million fans at Soldier Field in the 2018 football season. It only takes a fraction of that many Bears backers to contribute mightily to drivers’ coffers. I have done some Bear trips. However, it’s Soldier Field’s concerts where I’ve cashed in on trips. Beyoncé performances filled the arena and my rideshare mobile on consecutive August dates in 2018. Taylor Swift and other big names have also helped my business with massive outdoor shows.

The Island

Northerly Island is host to the Huntington Bank Pavilion, a site that can hold 30,000 riders. The pavilion averaged over 25 concert dates per season (typically May-September) from 2016 to 2019. Shows on the island’s grounds have provided me with many moneyed trips due to the numbers quoted.

The best aspect about these Near South Side attractions is that trips going there can begin anywhere. I tend to pick people up in the city when driving to these fan-favored destinations. But, trips do come from afar. I once drove a couple from a southwest suburban hamlet to the Adler Planetarium (at least 30 miles) for a black tie affair. This happened on one of my first Saturday evenings as a rideshare chauffeur. And, good trips to featured attractions and events like that continued.

A McEvent, November 6, 2012

A McEvent, November 6, 2012



McCormick Place is more than a convention center. It is a complex with a Hyatt hotel attached and a Marriot nearby. The urban compound includes a C.T.A. (Chicago Transit Authority) and Metra regional rail stops, along with arguably the best rideshare pickup/drop-off zone in the Chicago area.

McCormick Place, in my humble opinion, influenced by an estimated 9,000 trips, is the best single location to get riders who are going to the airports. It’s also a favorite destination of rider guests coming from Midway Airport.

North America’s premier meeting place maintains a busy schedule. McCormick is hosting global guest gatherings nearly every week throughout the year. I’ve picked up and dropped off passengers on city and suburban trips alike.

The Near South, with its location and featured attractions, is a proven place to profit for rideshare drivers.



This article is accurate and true to the best of the author’s knowledge. Content is for informational or entertainment purposes only and does not substitute for personal counsel or professional advice in business, financial, legal, or technical matters.

© 2020 James C Moore


James C Moore (author) from Joliet, IL on September 08, 2020:

Ms Dora

This area is popular with riders and drivers alike. However, it's been slowed down by the pandemic like everything else.

Dora Weithers from The Caribbean on September 07, 2020:

I'm sure that this is a very helpful guide to those who plan rides to the area. Because of your information, they can select wisely where they would like to spend their time.

James C Moore (author) from Joliet, IL on June 26, 2020:


Yes, Chicago is large. But, when you break it down by neighborhoods and communities it becomes much more manageable. It's a bunch of small locales that add up to become a big city.

Adrienne Farricelli on June 26, 2020:

Hi James,

I have only been to the Chicago airport which remains my favorite out of all the USA airports I have visited. I love all the flags and how easy it is move from one gate to another. The stores and food court are so nice. I have never exited the airport though. Kudos to you for offering rideshare services in such a big city like Chicago! I see now why you have several articles covering this topic since this city is so huge.

James C Moore (author) from Joliet, IL on March 26, 2020:


Chicago is huge but manageable. But, I'm used to it. Having been to but never driven in Los Angeles and New York, I shudder at the prospect of doing the same job in those towns. Neither seems manageable. I appreciate your perspective.

billybuc on March 26, 2020:

I don't know how you do it. I really don't. I would be a crazy man in a city of that size. I look at pictures of Chicago or New York or Los Angeles, and I can feel my heartbeat increase. :)

James C Moore (author) from Joliet, IL on March 04, 2020:


Thanks for visiting. Glad you liked it.

logicwebsolutions on March 03, 2020:

this good articles

FlourishAnyway from USA on March 03, 2020:

That's good to know that people are respectful of you as well as your property!

James C Moore (author) from Joliet, IL on March 03, 2020:

Always Exploring

Chicago is big but it's not unwieldy like Los Angeles is and New York City appears to be. But perhaps I wouldn't feel that way about those places if I had more experience driving them. Thanks for stopping by.

James C Moore (author) from Joliet, IL on March 03, 2020:


It may surprise you but I've never objected to people eating in my car. I would clean the car out and sprayed disinfectant and scent sprays on a regular basis.As for smoking, I just politely tell them no. I've had people openly complain about things but dont recall an instance of them being verbally abusive. I'm going to ask my rideshare driving brother the same question. He's never spoken of any such things but you never know.

FlourishAnyway from USA on March 02, 2020:

I’ve never taken Lyft or Uber cars. Do you have problems with people smoking or eating in your car, being abusive verbally or engaging in other rude behavior?

Ruby Jean Richert from Southern Illinois on March 02, 2020:

It sounds like you enjoy your work in Chicago. Large cities are not for me, but small towns bore some people. Thanks for the trip around the windy city.