Updated date:

The Chicago Drivers Guide to Rideshare Street Smarts: Follow the Money/10 Best Locations

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


map Chicago communities

map Chicago communities

Location, Location, Location

The familiar mantra "location, location, location" is used to explain business success for everything from real estate to restaurants. Rideshare, the chauffeur on demand service offered by Uber, Lyft, and Via follows the same model. Location matters.

How to Follow the Money

Chicago is a city of neighborhoods. I've found the best way to get rideshare dollars is by going to the busiest areas. Here, I list Chicago's 10 best locations to drive with a note about what makes them great.

 View from Fulton Street. The Kennedy I-90 has direct entrance/exit ramp access to 6 of the 10 best rideshare locales.

View from Fulton Street. The Kennedy I-90 has direct entrance/exit ramp access to 6 of the 10 best rideshare locales.

The 10 Best Places for Chicago Rideshare Driving


(the) Loop


Near South Side

Hyde Park

River North



Lincoln Park

Wicker Park


1. The Loop

In the Loop

Corporate offices, government, retail, hotels, and world class parks lie within Loop confines. As such, it’s an ideal place for drivers to ply their rideshare trade.


Many people employed in Chicago take public transportation to their jobs. Often, I've taken riders to transportation depots on route to the Loop. Suburbanites board trains bound for the Loop.They arrive at the Ogilve Transportation Center LaSalle Street and Union Stations.The C.T.A.'s (Chicago Transit Authority) color coded "L" trains provide city dwellers with round trip service.

Rideshare Residences

The Congress and Hilton Chicago hotels on Michigan Ave attract mad rider revenue. Millennium Park Fairmont and the Hyatt Regency among others help make the New East Side a day and night driver delight. And yet, these are only the tip of a large Loop lodging iceberg.

Tourist Draws

Parks adorn the lake front. The Art Institute and “the Bean” are located on park space. Festivals such as the “Taste,” Lollapalooza, and other massive fare producing gatherings occur here.

The Willis Tower, formerly known as the Sears Tower, generates tall rider traffic. The Loop’s is good on days, weeks, and throughout the year.

The 606, an old railroad trail that's now a bicycle, jogging path.

The 606, an old railroad trail that's now a bicycle, jogging path.

2. Bucktown

Bucktown maintains a strategic presence for my rideshare driving.The Armitage Ave, Kennedy exit leads to the uber busy (pun intended) Clybourn Metra regional train station. The Union Pacific North and Union Pacific Northwest train lines arrive here with each making more than 30 inbound stops every weekday.

The station’s limited parking and four corresponding bus routes add to the fares potential. Armitage Ave connects with Ashland and Elston Avenues, which lead to rider frequented retail sites in Bucktown and neighboring North Center.

Mega multi-unit buildings are scarce in Bucktown but rider request are still plentiful. The area bordered by Armitage, Bloomingdale, Ashland and Damen Avenues, (north,south, east, west) is that way. It is a fare full place with rides requested day and night.

3. Hyde Park

Hyde Park is an urban nirvana. Diverse people work, live, and peacefully coexist here. The University of Chicago serves as neighborhood pillar. Its vibe affects the economy and ride fares reality.

Big Rideshare Man on Campus

College campuses maintain a distinct context. Traffic flow is less reliant upon peak periods. Students move about throughout the day. This enables drivers to do a lot of short distance trips within little distance without driving that many miles. This helps when I drive in pursuit of bonuses based upon trip numbers.

Off Campus

The University anchors Hyde Park, but it’s not the whole ship. The Museum of Science & Industry draws the tourist crowd. Lake Park Ave and 53rd Street bustling retail/restaurant scenes generate rider fares. Three of the rider richest condo/rental buildings in all Chicago belong here. To be fair, the greatest of these, Regents Park is actually located in Kenwood, the north neighbor. Hyde Park’s unique qualities make it my favorite south side location..


4. Lakeview

Lakeview borders the lake and is near the Loop. The location attracts residents. The amenities lure revelers. Both bring in rider fares.

Sheridan Road/Inner Lake Shore Drive from Diversey to Irving Park Road offers the best two straight street miles of rider rich housing in Chicago. Lakeview’s remaining residential area contain a host of sites that contribute to a prosperous morning rush hour experience.

Holy Rideshare Cash

Wrigleyville is a neighborhood within the Lakeview community. It delivers a grand slam’s worth of riders traffic during Chicago Cubs home games. The Wrigley bar scene hits a home run’s load of riders during away games. The proliferation of bars and restaurants isn’t limited to Wrigleyville. The Schoolyard, Roscoes’ and Four Shadows are three of many non Wrigleyville wateing holes thats provided me with multiple trips. The park land around Recreation Drive includes part of the Lake Front Trail and Belmont Harbor giving rise to prolific seasonal fares.

Lake Shore Drive goes through 6 of Chicago's 10 best rideshare locales.

Lake Shore Drive goes through 6 of Chicago's 10 best rideshare locales.

5. Lincoln Park

Lincoln Park is a vibrant urban hamlet that includes luxury housing, industry, theater and fare rich DePaul University. An audience of three million potential riders visit the critters in Lincoln Park Zoo annually.

Main Streets

Clark Street, with its diagonal route, moves two directions at once on route to Rogers Park. The Lincoln Hotel, along with several area businesses reside there. Lincoln Ave is another shop filled street accessing the area. Fullerton Street includes the rider packed Red and Brown line Sheffield “L” station.

Morning Cup of Go

Lincoln Park is a great place for morning cups of go. These are shared rides where commuters get in the same car near one another and go to different stops outside the area. Some travel far.This enables drivers to get many rides and money rides when at least one rider travels far. I get quality and quantity rides with such car loads.

The Adler Planetarium

The Adler Planetarium

6. Near South Side

The labels city center and south side accurately describe this region. It includes the best of both city worlds, high powered resident and visitor demand.


The residential area bordered by Roosevelt Road, 18th Street, and Michigan Ave to the north, south, and west is like the Loop’s New East Side. It’s less than one square mile but surpasses most city locales with rider volume.

Museum Campus

The Shedd Aquarium rest between two other top 25 tourist attractions. Northerly Island holds a concert venue with a seating capacity of 30,000 riders. The 2019 schedule has 20 seasonal concert dates. Capacity multiplied by concert dates equal beau coup business. Soldier’s Field, home of Da Bears also host concerts

McCormack Place

North America’s premier convention draw is headquartered on King Drive.

It welcomed more than 2.5 million guest in the year 2017.[2] It like Navy Pier, has efficient rideshare zones. These factors explain why I have received more airport request from here than any other single Chicagoland location.


7. River North

River North rivals the Loop as a destination for riders due to its zoo; the Hubbard Street Zoo. Those who don’t think Hubbard Street has a zoo should try driving there on weekends between midnight and 3 a.m. Guest of the lively dining, bar, entertainment scene spill onto the streets in an urban wildlife extravaganza. Cabbies who turn left from the furthest right lanes coexist with wayward walkers oblivious to green lights. Rider fare opportunities proliferate from 6 p.m.onward weekend nights. Days are good too. The morning includes a traffic adrenaline rush.

The River of River North

The East Bank Club and Groupon’s massive rider request rest on one branch (north/south flowing) of the river. The Merchandise Mart (pictured) anchors the other branch. A glut of high rider traffic residences within the community lie within ½ mile of the river. A cluster of 10 high powered rider traffic condo/rental properties lay near river banks just beyond the River North community. The river rolls with ride fare fortune.


8. Streeterville

Streeterville is one of four officially designated Chicago neighborhoods (77 total) that share a coastline with the Chicago River and Lake Michigan. The other three, the Loop, Lincoln Park, and Near South Side are also among the 10 best locations to drive rideshare. Waters lead the way to trips awash with cash.

Boatloads and Full Houses of Trips

Navy Pier, situated east of Lake Shore Drive, is a proven place to drive. The mayor’s office claims that over 9,000,000 visited there in 2016.[3] These totals add up to abundant rideshare traffic throughout the year.

The 875 N Michigan Ave bldg. (i.e. John Hancock) supplies dependable fares on a daily basis. The Intercontinental, Omni and Westin hotels stand out among at least 20 area hotels that has provided much business for me. Lake Point tower among other private housing bring plentiful rideshare traffic. Streeterville is replete with retail and restaurants to go along with its lucrative lodging.


9. Wicker Park

Business Bonanza

Wicker Park allots around three miles of street space to commerce. Bars, dining and entertainment spots along with retail attuned to urban millennial taste fill Division Street, Milwaukee and North Avenues. This business creates high level rider traffic especially on weekend nights. When I drive here, night business is bright business.

True Blue

The Damen Ave Blue Line “L” stop is uber busy. (pun intended) It served nearly 2.2 million commuters/potential rideshare fares in 2017.[4] The “L” centrally located is a few city steps away from Wicker’s named sake park. The estimated 27,000 people per square mile and three bus routes contribute to its activity. [5]

10. Evanston

Evanston is both far and near. It’s “L” train accessible while still suburban. It shares Lake Michigan’s coast line with six other top rideshare locales. And it has the Northwestern University (N.U.) main campus.

Distant and Distinct

Evanston borders Chicago. Often, request for nearby Chicago pickups are received there. Still, it’s a good source for long city bound trips. The Orrington Ave Hilton generates many 15-20 mile trips to O’Hare and the Loop without immediate access to expressways. Long mileage plus long time equal long fares.

The town center includes at least four other multi-unit residential buildings that produce rider fares. The off campus housing, Sheridan Road’s N.U. stretch and the remainder of town also attract frequent rideshare request. Evanston offers good quality and quantity of trips during peak and non-peak hour periods. I love Evanston driving.

The 10 locations listed are the best ones out of many Chicago locales to make rideshare money. This is by no means an exclusive list of good Chicago driving areas.


[2] http://www.mpea.com/wp-content/uploads/2018/02/MPEA-annual-report_FINAL_2_1.pdf

[3] https://chicago.curbed.com/2017/4/6/15207352/millennium-park-navy-pier-attraction-attendance

[4] https://www.transitchicago.com/assets/1/6/2017_CTA_Annual_Ridership_Report.pd

[5] http://www.city-data.com/neighborhood/Wicker-Park-Chicago-IL.html

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


Miebakagh Fiberesima from Port Harcourt, Rivers State, NIGERIA. on May 14, 2019:

Well noted, please.

James C Moore (author) from The Great Midwest on May 14, 2019:

Hi Flourishanyway,

Glad to hear from you. Uber and Lyft are not ideal for long distance. I am 30 miles from Midway Airport. The last time I flew was the last week of July and first weekend of August 2016. (I dont get out much) I ended up taking the bus to and from the airport. The one way Uber rate was roughly $60.

Miebakagh Fiberesima from Port Harcourt, Rivers State, NIGERIA. on May 14, 2019:

Uber was recently introduced into Nigeria. It is operating at Abuja, the country's capital. And at Lagos I think. Thanks.

FlourishAnyway from USA on May 14, 2019:

I’ve never actually used Uber or Lyft. One of my cousins has a college student who took an Uber long distance to see a boyfriend in another part of the state and it cost well over $400. Slow head shake.

James C Moore (author) from The Great Midwest on May 14, 2019:

I appreciate your reading and comments. I'm curious as to whether you have Uber or Lyft cabs where you're at.

Miebakagh Fiberesima from Port Harcourt, Rivers State, NIGERIA. on May 14, 2019:

I am not a cap driver. Accept my pleasure in reading and informative and useful guide. Thanks for sharing.