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Chicago Driver's Guide to Rideshares: Busy Boulevards and Michigan Ave

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

875 N. Michigan Ave

875 N. Michigan Ave

Rideshares in Chicago

“State Street / that great street,” Frank Sinatra croons in a lyrical homage to Chicago. To me, Michigan Avenue is a great street, especially when it comes to rideshare driving. It offers tremendous money-making opportunities. Here's what you need to know.

Michigan Ave South Side Significance

Michigan Ave is not a boulevard for its whole length. Its non-boulevard south side trek flows practically uninterrupted from 31st Street towards the southernmost city limits. Here it runs north to south and includes southside enclaves Bronzeville, Washington Park, Chatham, and Roseland. It displays value outside the city center.


Michigan rolls through this historic area with five intersections within ½ mile of Loop-bound entrances to the Dan Ryan Expressway and nearby access to four Green Line “L” stops on the city’s color-coded rail system. The 35th Street intersection is less than a mile to Guaranteed Rate Field, home of the Chicago White Sox, and a major Rock Island Metra regional train stop.

Washington Park

Michigan’s Garfield Blvd intersection is within ½ mile of the Loop-bound entrance to the Dan Ryan Expressway. The same intersection is part of a mile-long stretch within two miles of rider/trip-rich Hyde Park. And this street provides nearby access to three Green Line “L” stops.


Chatham’s Michigan street cred consists of three intersections within ¼ mile of Loop-bound entrances to the Dan Ryan Expressway and two of them are that close to Red Line “L” stops.

95th St Red Line transit depot

95th St Red Line transit depot


A Michigan Ave drive offers close access to five Metra Electric Line regional rail stations. The 95th St corner is veritable walking distance to the 95th St Red Line transit depot (pictured). The 111th street corner is about a mile-long shot to the Loop and Indiana-bound entrances to the Bishop Ford Expressway.

Sometimes, I begin my city morning peak hour trips with Roseland and Pullman area pickups. It’s typically Michigan Ave and 111th and 115th Streets that play a part when that happens.

Boulevard Street Cred

Boulevard Street Cred

Michigan Avenue is a boulevard from its north point that leads to both the inner and outer Lake Shore Drives, going south to Cermak Road. This represents less than four miles of its approximate 12-mile length. However, it’s here where it puts the bull in boulevard.

It provides a fairly quick drive compared to other north/south streets over the same distance. The most synchronized traffic lights anywhere in the city contribute to its good traffic flow, particularly on the Mag Mile. As a result, it’s an uber-efficient ride for people to get a Lyft to their destinations “via” a rideshare car. (puns intended)

The mighty Michigan boulevard runs through three of Chicago’s ten best rideshare driving locations:

1. Streeterville

The “Mag Mile” resides here. The icons and shopping scene along the boulevard give rise to its name. The mile itself is a tourist draw, a commercial district, and a distinct Chicago neighborhood all in one. Icons that double as good sources of trips are here. The Water Tower and 875 N Michigan Ave, formerly known as the John Hancock Center (cover picture) come to mind. Apple, Bloomingdales, and Michael Jordan’s Restaurant also stamp their brands upon this street.

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The Intercontinental, Omni, and Westin hotels each have afforded me multiple trips. I have completed many trips to/from at least 10 additional hotel properties on the mile or within a block of its magnificence. The mile is magnificent for business.

Michigan Avenue connects the Loop and Streeterville via the DuSable Bridge. The sturdy steel structure is named in honor of Jean Baptiste Point DuSable , a renowned explorer, entrepreneur and the city’s Haitian born founder. As such, the bridge is more than a link to two of Chicago’s premier business districts/tourist draws: it’s a link to the town’s history.

Jean Baptiste Point DuSable, Chicago city founder

Jean Baptiste Point DuSable, Chicago city founder

2. Near South Side

Michigan Ave puts drivers within reach of the most concentrated mass of people/rider draws in the city. The museum campus features the Adler Planetarium, Shedd Aquarium, and the Museum of Natural History.

Soldiers Field, home of the Chicago Bears and two sold-out Beyoncé concerts in 2017, is near the campus. Northerly Island’s Huntington Bank Pavillion, which draws large crowds of potential riders to live performances, is also close by. Beyond the campus, towards Cermak Rd, the avenue puts drivers near the rider-normous McCormick Place complex.

The Loop

The Loop

3. The Loop

Michigan Ave looms large here. The quarter-mile stretch between Wacker Dr. and Randolph St provides the west boundary to Chicago’s trendy New East Side neighborhood. The Randolph corner also boasts the busy yet non-descript street-level entry to the lower level Millennium rail station. Access to the city’s vaunted subterranean pedway system is also provided in this area.

The Loop has at least 30 rider revered residences. The mile-long stretch of Michigan from Randolph St to Roosevelt Rd is host to six such places including the Congress and Hilton Chicago. It is also the west street front of Grant and Millennium Parks. Lollapolooza, the Taste, and other massive audience/rider gatherings occur at these parks.

Boulevard or street, Michigan Avenue is a street serious Chicago rideshare drivers should get to know.

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.

© 2019 James C Moore


James C Moore (author) from Joliet, IL on October 09, 2019:


You have a good ideal but I'm not the one to compare. I've never driven for Lyft. However, I can compare Uber and Via. That hub may be coming soon.

FlourishAnyway from USA on October 09, 2019:

I liked the puns. A good article might be a head to head comparison of Lyft and Uber based on your experience.

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