Chicago Streets: Ten Streets to See When Visiting Chicago

Where to Drive in Chicago

Chicago has so much to see and do that one will get the best sense of what the city about by getting behind the wheel and taking a ride. The best times of day to travel in the city without too much traffic is in the late evening or nighttime, any day of the week, or early Saturday or Sunday morning when most Chicagoans are off the streets. Where to drive, you ask? To help you make that decision, I'm suggesting 10 Chicago streets you'll want to travel to see Chicago - starting with the obvious first choice!

The Ten Must-Travel Streets in Chicago

1 - Lake Shore Drive – LSD, as it is often called locally, runs with an amazing view of Lake Michigan on its east side for its entire length. On the west side of it, you see the city’s tall buildings and architecture which is referred to as ‘Chicago’s Skyline’ at the city’s loop level (or downtown). Its entire length travels from Hollywood Boulevard near Chicago’s north border to the Hyde Park neighborhood near 57^th Street on the south. There are exits to parks, beaches, neighborhoods, and the loop (downtown) that you can take to get off of it so you can actually spend time enjoying the views without becoming entranced while driving. Be aware the first time you travel LSD that there is an S-curve just north of the John Hancock Center which can be tricky to navigate if you’re not familiar with it. The S-curve is pretty much what the term implies; it’s curving your vehicle to the left-then-right in the shape of an S. Though it might sound like fun, it can be challenging to the novice when he or she has several jam-packed lanes of cars and trucks ‘having fun’ at the same time. Besides the above mentioned sights along the Drive, from the south a traveler passes the Museum of Science and Industry, south side Chicago neighborhoods, McCormick Place, Soldier Field where the Chicago Bears play football, the Field Museum, the John G. Shedd Aquarium, the Adler Planetarium, Grant Park which hosts concerts and most notably ‘The Taste of Chicago’ in the summer, the John Hancock Center, Navy Pier, and finally the north lakeshore neighborhoods. There was a 1971 hit song called “Lake Shore Drive” (and is about the Drive) by a local group of musicians, Aliotta-Haynes-Jeremiah; the well-crafted lyric makes references to the many wonders surrounding Lake Shore Drive.

2 - State Street – State Street is a very well-known north-south street which runs from North Avenue (2000 north) on the north end where there are mansions and large apartment buildings, down through a north side business district with major hotels, then crosses over the Chicago River to claim one of the most famous stretches of street in the city – State Street’s downtown shopping area. Among the many State Street stores in the loop (downtown), Macy’s, which is in the former Marshall Field’s building and store, is likely the most famous as it is 14 stories of shopping. Also along State Street in the loop, one can see the Chicago Theater and ABC-TV (WLS) studios at street level on the north end, the L-tracks and trains (elevated train) above the State and Lake intersection, and the Harold Washington Library at the south end. The street is alive with shoppers and people working in the area during the weekdays. South of Congress Parkway, the south end of the loop, State Street continues all the way down to the southern tip of Chicago where it ends at the Calumet River near 127^th Street. The classic song “Chicago” by Frank Sinatra makes mention of “State Street – that great street!”

3 - Michigan Avenue – The Magnificent Mile, as the shopping district of Michigan Avenue is called, is located from the north-most point of the avenue at 950 North Michigan Avenue and travels a mile south of that point. However, Michigan Avenue continues, much like State Street, from the near north side of the loop down to about 126^th Street on the far south side of Chicago. The famous stores along the Magnificent Mile include Water Tower Place, a very popular mall, and Chicago Place, another mall blocks south of Water Tower. In that area, one can also see the architecturally-amazing John Hancock Center and the original Water Tower on the north end and the Art Institute as well as the massive Grant Park at loop-level, downtown. Michigan Avenue also bridges across the Chicago River at which point one can see the historical Wrigley Building on the north side of the river. Christmas holidays are special along the Magnificent Mile as it is the city’s most-renowned Christmas-decorated street.

4 - Clark Street – A drive down Clark Street will definitely give one a sense of Chicago and its history. It starts at the Chicago-Evanston borderline as one enters Chicago from the north and runs all the way down to 2200 South Clark Street where it finds Cermak near Chinatown. For travel purposes, one needs to know that Clark Street is one-way south from Division Street (1600 north) to the south through the loop (downtown). Between Evanston and Cermak, along Clark, there is much history including the well-known Andersonville, Wrigleyville, and Lincoln Park neighborhoods as one travels south. Wrigley Field, where the Chicago Cubs play baseball, is at Addison on the north with the huge Rock ‘n’ Roll McDonalds and Hard Rock Café establishments in the upper-crust's River North neighborhood on the near north side just north of the Chicago River, then Daley Plaza and the Thompson Center downtown at loop-level, and finally, the south loop area which now showcases some of the most recent real estate developments in the city.

5 - Halsted Street – This street runs north and south through most of the length of the city at 800 west – just a few blocks west of the loop area. From the south border of Chicago, the Calumet River, it can be traveled up to 3800 north in the Lakeview neighborhood on the north side where it ends. After travelling through the south side neighborhoods of various types, including a drive through Bridgeport, the two Daley Mayors’ neighborhood, it shows various Chicago characteristics when it enters the historic Maxwell Street area which is changing drastically with new buildings and architecture (to the dismay of many who wanted to preserve the area). From there, one passes the University of Illinois at Chicago’s campus, passes over the I-90 expressway to Greektown, passing many eateries just a couple of blocks east of Harpo (Oprah Winfrey’s studios) as well as many warehouses-turned-night spots and turned-residential lofts, then the Cabrini Green housing complex at Division Street (1600 north), followed by the north side neighborhoods with stores, neighborhood bars, and more restaurants beginning around North Avenue (2000 north). After continuing north through the yuppie neighborhoods near Lincoln Park and DePaul University, the last couple of miles of Halsted Street’s north end is Chicago’s Boystown neighborhood which is the center of the gay nightlife. As one can see, many characteristics of Chicago can be seen with a drive up and down Halsted.

6 - La Salle Street – The famed financial district isn’t lengthy, but it’s where Chicago’s monetary giants are located. It’s another one of the many one-way south streets through the loop, ending at a T-crossing where the infamous Board of Trade building stands near the south end of the loop at Jackson and LaSalle. North of the Chicago River, LaSalle is a two-way, four lane street which travels through the River North neighborhood past Rock ‘n’ Roll McDonalds and other eateries, the Moody Bible Institute, apartment buildings, and ends when it curves to become an extension to Lake Shore Drive at about 1800 north, just north of North Avenue (1600 north)..

7 - Western Avenue – If for no other reason than to say “I’ve traveled the length of Chicago’s longest street and have seen all the neighborhoods it goes through,” travel the 26 miles of Western Avenue from one end to the other. Start at either the north or south end of Western Avenue, which is three miles west of State Street downtown at 2400 west. Watch for motorists, bikers, buses, taxis, and pedestrians as they are all seen along this 4-lane, 2-way main thoroughfare all day and practically all night. One can see Chicago’s northwest, west, and southwest areas and their varied neighborhoods, including the notorious Humbold Park area which houses much of Chicago’s Puerto Rican population on the near northwest side near Western and Division Street (1200 north) and west of there, African-American neighborhoods just north of the I-90 expressway, many hispanic neighborhoods on the near southwest side, and more African-American neighborhoods beyond the hispanic neighborhoods farther to the south and southwest areas.

8 - 26^th Street – To sample one of the many large culturally-immigrated neighborhoods, if not the most prominent in Chicago, travel the length of 26^th Street, a 2-way east-west street that passes through the Little Village neighborhood. From 26^th Street and Western Avenue west to 26^th and Kostner, approximately two-and-a-half miles, a traveler feels as though he or she is in Mexico without the travel and expense of actually going there. Of course, the is quite a difference in weather between the two. This short drive passes the largest county jail in the United States at 26^th and California. It also passes the Discount Mall at Albany Street, and from Kedzie to Kostner, most everything – store names, signs, and the voices of the locals heard - is in Spanish. One sees street vendors with Mexican food and drink, articles of clothing, and more for sale every block or so.

9 - Lincoln Avenue – One of Chicago’s many angled streets, Lincoln Avenue angles its way from about 1800 north on the north side of the city, where famed and formerly folksy Wells Street ends, and continues northwest through the city’s northwest side neighborhoods. This avenue begins just a few blocks west of Lake Michigan off Clark Street where there are many lively restaurants and bars. The dining and drinking establishments are strategically located as one travels on through the northwest side of the city where the older European-settled neighborhoods are found.

10 – Archer Avenue – This avenue is as well known in the southwest suburbs as much as it is known in the Chicago city limits. It is actually a 4-lane, 2-way highway, Route 171 which winds its way from southern Illinois up to Chicago’s south side near the lake where it ends at its northern most intersection. Along this route, you will find many restaurants and businesses running through the south sides old European neighborhoods where many Polish people settled near the southwest end of Archer near Midway Airport near 55^th Street. Many drag racers have laid rubber and gotten ticketed by police on Archer Avenue, though fewer in recent years.

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The design of the Chicago streets is fascinating and quite logical. It all starts at the four corners of State Street and Madison Avenue and sprawls out from there. State Street runs north and south while Madison Avenue runs east and west with the numbering of blocks and buildings starting from 0 at this intersection and extending out in all four directions: north, south, east, and west. Each city block has a new number, by hundreds with the last two digits of an address being even numbered if it is on the west side of a north-south street and on the south-side of an east-west street. If a block isn’t a complete city block in length going south, the street between the two city blocks is called ‘place’ instead of ‘street.’ Therefore, when traveling south, 25^th Street may be followed by 25^th Place before reaching 26^th Street. Traveling east and west, there are ‘courts’ as well as ‘avenues’. Therefore, when traveling west, 49^th Avenue may be followed by 49^th Court before reaching 50^th Avenue. For calculating or estimating distances, know that every 8 city blocks is a mile. Understanding the labeling and numbering of addresses in Chicago is a great asset to getting around. If someone points you in the general direction of where your destination is, finding an exact address should be logical.