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

Updated on March 10, 2020
justthemessenger profile image

James has driven rideshare good through all 77 Chicago neighborhoods.

Shedd Aquarium with city in background
Shedd Aquarium with city in background | Source

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 coast line 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 | Source

Da Chicaguh Drive Demand Directory

Rider(s) - leave from or return to their homes
Pickup 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

Neighborhoods that provide two sources of extraordinary demand will make you money. Chicago’s Near South Side boast of 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 little, ( estimated 1 mile north/south ½ mile east/west) its rideshare demand is large. Dearborn’s State Street presence produce 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.

Meigs Field

Chicago used to have a lake front airport. Now its Northerly Island an urban nirvana.
Chicago used to have a lake front airport. Now its Northerly Island an urban nirvana. | Source


The Museum Campus

Near South Side venues offer the most concentrated collection of cultural and crowd pleasing settings in all 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 enable 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 have provided me the most instances of passenger drop-offs immediately followed by new pickup request.

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 ridesharemobile on consecutive August dates in 2018. Taylor Swift and other big names have also helped my business with massive outdoor shows.

Northerly Island, Burnham Harbor

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 and 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 theses 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 | Source



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 guest 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 content is accurate and true to the best of the author’s knowledge and is not meant to substitute for formal and individualized advice from a qualified professional.

© 2020 James C Moore


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    • justthemessenger profile imageAUTHOR

      James C Moore 

      10 days ago from The Great Midwest


      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.

    • alexadry profile image

      Adrienne Farricelli 

      10 days ago

      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.

    • justthemessenger profile imageAUTHOR

      James C Moore 

      3 months ago from The Great Midwest


      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.

    • profile image


      3 months ago

      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. :)

    • justthemessenger profile imageAUTHOR

      James C Moore 

      4 months ago from The Great Midwest


      Thanks for visiting. Glad you liked it.

    • profile image


      4 months ago

    • FlourishAnyway profile image


      4 months ago from USA

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

    • justthemessenger profile imageAUTHOR

      James C Moore 

      4 months ago from The Great Midwest

      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.

    • justthemessenger profile imageAUTHOR

      James C Moore 

      4 months ago from The Great Midwest


      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 profile image


      4 months ago from USA

      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?

    • always exploring profile image

      Ruby Jean Richert 

      4 months ago from Southern Illinois

      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.


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