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The Chicago Drivers Guide to Rideshare Street Smarts: City Center/Lakeview

Updated on September 5, 2021
justthemessenger profile image

I drive people to their destinations as I drive towards my destiny.

Lakeview "residents"  enjoying a walk by the harbor.
Lakeview "residents" enjoying a walk by the harbor. | Source

Lakeview has its name for a reason. It’s among the seven of Chicago’s ten best rideshare driving areas with a Lake Michigan coast. The region doesn’t have any point within it that’s more than two miles west of the water front.

The Lake Affect

Lakeview’s share of Lincoln Park is readily accessible from DuSable Lake Shore Drive. The Recreation Drive exit from north bound DuSableLake Shore Drive leads to park area. The Irving Park Road (Rt. 19) exit leads there as well. Irving Park Road itself goes into the park area.

The Lake Front bike and hike trail cuts through the park. It crosses paths with a bevy of outdoor recreational options that help make Chicago a summer time favorite. Belmont Harbor, a liquid Lakeview playground for the boater set, contributes to that summer scene. Often, I’ve picked up riders from their harbor docked boat sites.

A glance at real estate listings reveal that people are willing to pay for the lake view. The region has approximately two miles of lake front road way. The high price high rises (and low rises) generate business regardless of when I drive.

Belmont Harbor


Legendary Lakeview Link in the Rideshare Trip Chain

Last trip on first New Year’s Eve shift, January 1st,2016

Lakeview to Central Loop hotel

The surcharge was on after midnight. The two riders were friendly, one in particular offered encouraging words to me.The five trip mile paid out over $50.

Beyond the Lake

Brown Line stop as viewed from Lincoln Ave.
Brown Line stop as viewed from Lincoln Ave. | Source

A population of over 70,000 people inhabit this community’s relatively meager area. They’re not all along the lake front. The non lake front residents also contribute to my driver coffers. Money is made by the lake or away.

I’ve found that driving certain streets are key to get Lakeview’s rideshare riches. Belmont is the main east/west thoroughfare. However, like its compatriot Addison it’s not a particularly fast moving street. School/Aldine is a viable alternative when going east bound. Similarly, Roscoe offers a west bound option. Belmont, however, does include the only neighborhood “L” stop that allows transfer to three lines (red, brown, purple) on the city’s color coded rail system.

Irving Park Road (Rt. 19) and DuSable Lake Shore Drive (Rt. 41) provide highway avenues that give drivers fairly quick access east/west and north/south respectively. Broadway, Clark and Lincoln’s diagonal streaks allow drivers to travel two directions at once. The Ashland Ave aisle travels from Diversey to Montrose avenues while in Lakeview.

Ashland Ave and DuSable Lake Shore Dr. are pivotal to morning cups of go and loop the Loop trips during the morning peak hours. Cup of go refers to a "pool" of rider pickups close to one another who are dropped off at diverse destinations. A Lakeview loop the Loop trip drops off riders in or near the Loop and is followed by me going right back to Lakeview for more fares.

Rider Street Smarts Tip

Ask smart, ask safe

Rider(s) as you approach the driver, ask him/her the following: What is your name? Don't ask are you James? Always make drivers reveal their names. Happy Riding!

Lakeview Lures


Lakeview’s map location is favorable. Locales that put Lakeview on the map also matter.

Wrigley Field

Wrigley is the home to that uber sports brand, the Chicago Cubs. Their following is such that attendance averaged more than three million fans per year from 2016-2019. These numbers supply a prodigious potential for rideshare trip request over a six month period. A cub related trip is nearly a daily occurrence when they’re in town. Wrigley Field also host concerts. I’ve taken people to see Billy Joel, Luke Bryan and the Foo Fighters among others.


The Wrigley ville is live even when Wrigley’s field is empty. I’ve taken riders to their local watering holes from all over the city and sometimes a suburb. Baseball has a season, but Wrigleyville is beyond seasonal.

Legendary Lakeview Link in the rideshare trip chain

1st of 3 upchuck trips

Division & Dearborn - Wrigleyville

The sad drunk rider was tossed into my front passenger seat by a male friend. Her drunken state amused my two other pool riders. I tried to drive smooth, cursing the city’s ragged streets, she and her “friend” in my mind. Then she hurled. The good news- I had barf bags handy. No puke on the car’s interior surface. The bad news- no damage on car's surface for a picture i.e. proof. So,no reimbursement for money spent to clean the car.

Lakeview’s non Wrigleyesque area has its share of entertainment and other varied destinations. The renowned Music Box Theatre with its featured movie classics is here. The Briar Street Theater with its iconic resident Blue Man Group belongs here too. And, this area has a double digit dose of bar/taverns that have supplied trips to me.

Lakeview, by the lake or away, in Wrigley or not, throughout the year it’s a good place to ply the rideshare trade.

This content reflects the personal opinions of the author. It is accurate and true to the best of the author’s knowledge and should not be substituted for impartial fact or advice in legal, political, or personal matters.

© 2019 James C Moore


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