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The Chicago Drivers Guide to Rideshare Street Smarts: Transit Avenues/Cicero Ave

Updated on August 11, 2021
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James has driven people from here to there with nary a care while driving Chicago rideshare. 9,000 trips by the 2019 new year.

The corner of Cicero and Belmont Avenues in Chicago's Belmont Cragin community
The corner of Cicero and Belmont Avenues in Chicago's Belmont Cragin community | Source

The Road to Rideshare Riches

I suspect that non Chicagoans think of State Street and Michigan Ave when it comes to Chicaguh streets. And, yes they’re right. Addresses located on the two renowned avenues play an integral part in Chicago’s traffic, economy and lifestyle. Though less famous, Cicero Ave (IL Rt.50) plays a major role in chicagoing travel. It connects to and directs towards many of the region’s important locales. As a result, it has contributed mightily to my rideshare experience.

Suburban Saturation

Cicero Ave cuts across key south and southwest Chicago-land suburbs. The south suburban stretch plows through 13 towns which include two particularly good stops.


The transit titan boulevard provides an approximately 3 mile long east border between Chicago’s west side and this road’s named sake city. Cicero along with fellow borderburb (border/suburb) Oak Lawn have delivered my best suburban business outside of Evanston and the “wonderful west” corrider.* It also helps contribute to Roosevelt Road’s prime suburban presence.

Oak Lawn

Oak Lawn has a habit of providing me with really good ($25+ payout) trips. It is here where Cicero Ave connects with Southwest Highway (Rt.7) which lead to multi trip generating sites such as Moraine Valley Community College located in Palos Hills and the Chicago Ridge Mall.

*“wonderful west” The west suburban area that includes the towns of Oak Brook, Oak Brook Terrace, Lombard and Downers Grove have been a wonderful rideshare drive experience.

City Locations

Cicero Avenue goes through and towards prime city locations. It touches upon Austin (west side), Belmont Cragin (northwest side), and Garfield Ridge near Midway. Cicero Ave goes near Archer Heights (southwest side), Edgebrook and Jefferson Park on Chicago’s far northwest side. A nearby southwest side area that combines parts of Archer Heights and neighboring West Lawn has produced outstanding morning peak hour business for me. The northwest side neighborhoods that Cicero Ave visits are fairly short drives to O’Hare without going on the expressways.

Homage to a Hero

The section of Cicero Avenue between Grand Avenue to the north and Roosevelt Road to the south, is now called Mandela Road. It’s named after Nelson Mandela, the lead figure in the movement to dismantle apartheid from South Africa. The renaming took place on the 96th anniversary of his birth date, roughly seven months after his passing. The fight for justice anywhere is respected everywhere.

Transit Avenue Street Cred: Airways, Railways and Highways



The road to Midway International Airport runs through Cicero Avenue. Midway’s arrival and departure terminals are easily accessed from both sides of the boulevard. Furthermore, Cicero traffic moves quickly towards Midway from either direction (north and south) compared to other streets.The Stevenson Expressway (I-55) has exits in both directions to Cicero Avenue.

Midway is the south end of the Orange Line “L” tracks. This stop on the Chicago Transit Authority’s (C.T.A.) color coded “L” train system (pictured) is an uber major (pun intended) transportation terminal. Regional and city buses representing 20 or more bus routes stop here. It also includes a “kiss and ride” area for auto passenger pickup and drop-off. Cicero Ave is the closest boulevard to this transit behemoth.

Midway’s giant hospitality housing headquarters are based in Bedford Park, a sparsely populated village with a formidable industrial and commerce presence. Here, it host a double digit dose of big brand hospitality housing. I’ve found this “hotel park” is a tremendous source of rideshare opportunity, especially on the weekends. Trips from here have taken me all over the Chicago area. And, unlike waiting for an arrival on Cicero Avenues' Midway rideshare car holding lot, I don't have to wait in line for my trips.

Cicero’s airway transit cred doesn’t stop with Midway. It intersects with an important street that I use as a shortcut to O’Hare while traveling from north suburbs, Evanston and Skokie, or Chicago’s far north side. The shortcut enables me to avoid the afternoon/evening rush hour standstill on the Kennedy (I-90) expressway’s path to O’Hare.

Rider Street Smarts Tip

“No pickup lines here”

Rideshare drivers should not approach people and ask if they need a ride.The app supplies your introduction to your driver.The airport announcement says it best… “anyone asking you if you need a ride shouldn’t be giving you one.” Happy riding!


Cicero Ave host four other C.T.A. stops in addition to Midway’s Orange Line stop. I have completed several trips to its Pink Line, Green Line and two O’Hare Blue Line stops. Metra, the regional rail system has at least six south suburban train stations that I’ve serviced within close proximity of Cicero Ave.


Cicero Ave supports immense access to Chicago regional highways. It cross other major streets such as Southwest Highway (Rt.7), Ogden Ave (Rt. 34) and Peterson Ave (Rt.14) in Chicago. It connects to the expressways also. It includes six intersections within three miles of I-57. The quick south suburban access to "57" (and thereby Chicago) is of tremendous value when in any of seven towns when their ride request dry up.

It has even closer access to I-290, the Eisenhower, I-94, the Edens, and I-90, the Kennedy. It has direct access to the premier tollway and closest expressway to Midway as shown here:

I-294 Tollway, the Tri-State

The toll road is also called the Tri State because it goes through Indiana, Illinois and Wisconsin. Cicero Ave has direct access to and from the tollway while in suburban Alsip.

I-55 the Stevenson

Direct access to and from within two miles of Midway.

Cicero leads to Midway. This alone would make it valuable, but it does so much more.

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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