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The Chicago Drivers Guide to Rideshare Street Smarts: Dominant Diagonals/ Archer Avenue

Updated on October 21, 2023
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James has driven rideshare through all 77 Chicago neighborhoods.


Archer Avenue began life as a trail carved out of the bogs by people native to North America. It shares such origins with diagonal counterparts, Milwaukee, Ogden and Vincennes Avenues.Today, it’s a thoroughfare that runs in a Northeast/Southwest angle parallel to the Interstate 55 (I-55) Stevenson Expressway. Archer’s north point intersects with State Street in the South Loop. Its south extreme occurs in the southwest suburban area as Route 171.

Archer cuts across Chicago communities Chinatown, (pictured) Bridgeport, McKinley Park, Archer Heights and Garfield Ridge between the South Loop and suburban Summit. The highway version, Route 171 South, slices through Willow Springs, Lemont, Homer and Lockport in route to its southwest suburban south point.

Rideshare Trip Down Archer/ Memory Lane

I worked at a company in Archer Heights for most of the 1990’s decade and into the millennium.The job wasn’t on Archer Ave but it was close. One time, I picked up a rider from my former employer and took him to Midway Airport.

The trip only lasted 10 minutes. So, my earnings certainly wasn’t cause to remember this. However, I do recall our conversation.I learned that much had changed since then. Yet, it's still there as Archer rolls on.

Glorious Morning


Radar and Regulars


The thoroughfares chosen for the “rideshare street smarts” series are the result of my driving experience. The honored avenues all lead towards enviable locations. However, each one has one or more distinctive traits.

Archer has the propensity to receive request nearby or miles away from any direction. It’s one of only three largely south side streets where this happens to me. Typically, Archer weekday a.m. radar gets me shared-ride car loads and Loop bound trips. It has worked at other times too. One Sunday afternoon, I picked up a car load of fellow White Sox fans at the ball park. I drove them to their south suburban, Indiana bordering town of Lansing, a 20 plus mile journey on the expressways.

The radar really works its mojo in and around Garfield Ridge. Here, I have picked up a.m. riders going to the Loop, North Side, West Side and suburbs in all directions. And, not just in the morning. This is especially true while driving on Archer Ave and on 63rd Street.


A repeat rider is one that I definitely remember taking on at least two trips. Archer Avenue is where I picked up my first city based repeat rider. I drove a student from the 35th Street/Archer Ave Orange Line “L” station to the Illinois Institute of Technology (I.I.T.) campus. I drove her back to I.I.T. at least two more times. Other repeat riders have followed since while cruising Archer.

Rider Street Smarts Tip

Again We Meet

I estimate that repeat riders have accounted for hundreds of trips. Likely, there’s way more. So you may remember your driver but he/she may not remember you. Please, don’t take it personally. Do the safe thing and let him/her tell you your name as you verify (not ask) his/ her name. Happy riding!

Dominant Diagonal Street Cred

Double Direction Distinction

A diagonal street’s unique advantage gives people the ability to travel two directions at once.The double direction anomaly allows Archer to cross with north/south streets and their east/west counterparts.The following examples demonstrate the Archer edge:

Cicero Ave Rt. 50, north and south bound-

The intersection with Archer puts travelers within ½ mile of Midway Airport terminals on either side of Cicero and within two miles of the best "hotel park" in the Chicago area.

35th Street, east and west bound-

The 35th Street corner is within a mile of Guaranteed Rate Field, (pictured) home of the Chicago White Sox, and the Dan Ryan expressway.

Trail of all Trails

Archer helped build Chicago. The Illinois and Michigan (I&M) canal, the C.T.A.’s (Chicago Transit Authority) Orange Line rails and the Stevenson Expressway align with Archer. The I & M was built as a navigable alternative to the original land based trail to provide a link between the Great Lakes and the mighty Mississippi River. In fact, Archer Avenue is named after William B Archer, the canal’s builder. The Orange Line trains on the C.T.A.’s color coded “L” rail system runs parallel to Archer for most of its course. The Stevenson (I-55) is the newer, faster version of Archer in Chicago.

Today, Archer acts as a quasi-frontage road to the Stevenson. It offers an alternative when traffic jams turn the expressway into a distress-way. Its nearby intersections add to its diagonal street cred as shown by the numbers:

9, intersections between bordering suburb Summit and Chinatown that lead to I-55 entry/exit ramps

8, such corners within 2 miles from the Stevenson

2, crossings less than a mile away

The Orange Line “L” rails run parallel to Archer Ave for most of its tracks. Archer’s presence with regard to the “L” displays its dominant status as shown by the numbers:

7, South Side Orange Line stations

5, Archer intersections less than 1 miles of an O’ line station

2, Orange line stations on Archer Avenue

Archer Avenue has proven its worth to me as a rideshare driver. It's as dominant as a diagonal street can get.

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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