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The Chicago Drivers Guide to Rideshare Street Smarts: Follow the Money/City Center- The Loop

Updated on May 14, 2020
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James drives people from here to there with nary a care when he drives Chicago rideshare. 9,000 trips by the 2019 new year.

Destination in Demand

the "Bean" Millennium Park
the "Bean" Millennium Park | Source

The Loop is the sun in the Chicagoland galaxy. The activity therein radiates throughout the city and surrounding metropolitan area. Downtown (i.e. City hall) decisions determine which streets in which city neighborhoods get their potholes filled. Its employment opportunities and entertainment options similarly affect the region.The area’s road and rail traffic movement follows suit.

The Loop’s popularity as a destination enables it to cast a pervasive shadow onto the rideshare experience. I begin my morning driver gig approximately 45 miles away from the Loop. I don’t bolt onto the expressways to make a beeline towards the Loop or any other super surcharged city locale. I’ve found it’s best to head towards the city while online and available for local trip request. The Loop impacts my driving even as I drive locally.

Don’t leave money on the road

If I drive 50 miles to chase a surcharge and don’t try to get a trip along the way potential earnings are passed up. I go through towns with combined population totals of over 350,000 people by simply driving 20 miles due east of my starting point. By the time I reach Chicago city limits the totals go up to ½ million. Why pass them up? I’ll change my mind when they start $100 payouts to go around the block in Lincoln Park.


I have taken distant suburban rides to the Loop on occasion. But, these are rare occasions. I begin most morning peak hour (5:00 a.m.-9:00 a.m. or 6: a.m.-10:00 a.m. depending on the season) Loop bound trips within city limits. Typically, I’ve driven workers from the south and southwest sides to their Loop located jobs. I’ve also taken morning fares from the airports, north and west sides to the Loop. However, this happens less frequently.

The Loop procures most morning trips indirectly by way of commuters. People headed to a core group of some 20 south suburban regional train stations have supplied me with multiple trips to each of these stops. To a lesser extent, I’ve taken west suburban passengers to Loop bound trains on the B.N.S.F. rail line.

Each of the C.T.A.’s (Chicago Transit Authority) 10 south side Red line “L” stations have received riders from my cab.This has been especially true of the 95th Street Dan Ryan transportation depot. (pictured) I have dropped off riders at orange, blue, pink, green and brown hued stops on the city’s other color coded rail line stations.

Rider Street Smarts Tip

When rideshare is a shared's not for the hurried at heart.

Uber Pool, Lyft Line and Via's default option are shared rides. One to three other people may ride along with you. And, one or all of them may be dropped off before you regardless of the order they entered the car.So, plan wisely.Don't allow a discounted rate make you late to your flight, interview or job. Give yourself some time or just pay for a private trip. Happy riding!

Precious pickup points

Willis Tower as seen from Greektown
Willis Tower as seen from Greektown | Source

The same collection of businesses, tourist draws, housing and transportation depots that makes the Loop a premier stop, also makes it a good starting point. It’s a good location to get an O’Hare or Midway going traveler. Also, one man’s trashed missed train is this man’s treasured rideshare drive opportunity. Treasured trips to suburban Aurora, North Brook, and Oak Forest among others have come to me this way. The 25-30 mile treks are especially good during the evening rush hour.


Deloitte with its estimated 4000 employees[1] is as good a place to pick up as it is a prime destination. It seems like I've taken half their workforce somewhere.

The Willis Tower

The "big Willy" is a source of tall rideshare traffic.It isn't simply the estimated 1 million annual visitors to the sky deck. It has 100 businesses and 15,000 people who work there.[2]

The Aon Center

This New East Side business has delivered plenty on both ends of the drop off and pickup rideshare experience.

The examples provided are just that, examples. These are just a few of the Loop offices filled with potential riders.


The Presidential Towers to the west and the Fairmont Millennium to the East are main courses to the feast of residences (hotels, condos and rentals) offered up by the Loop. I have completed multiple trips to over 30 other residential buildings in this city center.


[2] History and Facts

Featured Attractions

Buckingham Fountain
Buckingham Fountain | Source

A seemingly unending array of attractions dot the Loop. Chicago's downtown has two kinds of featured places that stand out. Its parks and skyline make it a place to visit. Grant Park, Millennium and Maggie Daley parks beautify the Loop's lake front.

The parks contain several icons and events that yell out Chicaguh! The Art Institute and Buckingham Fountain (pictured) rest in Grant Park. Lollapalooza and the Taste of Chicago take place in Grant Park. Millennium Park host the "Bean"(cover picture) and the Jazz Fest.

Lake/Clark "L" station
Lake/Clark "L" station | Source

Transportation Depots

The Loop is a proven influence in my taking suburban and city commuters to transport depots outside of it. The city center also has its share of transportation depots that supply rideshare trips. Many commuters go to and from the following transit hubs;

Union Station- This is a large station with many entrances and a bus hub at its south end.It serves Metra and Amtrak rail lines. Southwest Service rail stops in Orland and Palos townships lead here. These have repeatedly added to my trip total.

Ogilve Transportation Center-

This mega train station serves Metra regional rail lines for north, northwest and west bound trains.


The South Shore rail line begins in Indiana and ends here. Metra Electric line regional trains encamp here coming from the south suburbs.

LaSalle Street-

Obviously, this line ends at LaSalle Street. The Rock Island line stops along this line contribute much to my trip totals.

"L" Trains-

The separate rail lines that form Chicago's "L" system are identified by a color coding scheme. (e.g. the red line, blue line etc) Practically every color of the "L" train rainbow choo choos its way across the Loop.

Da Loop

The Loop has much to offer in food, entertainment, employment, business and just plain fun. It is a Chicago treasure that adds to drivers' coffers.

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.

© 2019 James C Moore


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