Get There

Getting to your destination is and should be part of the fun. For a HUGE city Chicago is super easy to navigate. Of course their are some quirks. But for now let’s get the basics down and work are way up…and down in to Lower Wacker!

So what you’re telling me is this funny sounding street name runs North, South, East & West? And there’s multiple levels too?

Here we go…

There are a lot of transportation options in Chicago. From your feet to a boat, we’ll cover ’em all. First, lets help you get a lay of the land. Trust me, if you are new to the city, visiting or want to get around a bit easier here’s some must have info for getting around…with a little history mixed in.

Quick history!

Prior to 1909 the city of Chicago was growing at a rapid rate like the world had never seen before. Not a lot of urban planning going on. In The Great Chicago Fire of 1871 most of the city burnt to the ground. With buildings still smoldering, rebuilding was already taking place. All of that quick rebuilding and annexing led to multiple streets with the same name and no real one starting point for the address system.


In 1901, Chicago had 13 streets called Washington, 13 called Center and 14 called Park. There were nine Forest streets, nine Sheridan streets and 10 Oak streets. Seven streets were called 40th, and eight were named 42nd. There were even five named for former U.S. Vice President Schuyler Colfax! You think you always got your mail? How did you give directions?

Enter Edward P. Brennan and Daniel Burnham

I could fill an entire website just on these two guys and urban planning…one site at a time. Brennan proposed that State and Madison be the nexus of the numbering system. All address would be based on that intersection being 0. There would be 8 blocks to each mile with 100 address per block. This gives us 800 address to each mile. So, if you are at 3200 N. you are on Belmont Ave., four miles North of Madison. Drive West to 4800 and you are six miles West of State street. This is kind of like Chicago’s own Latitude and Longitude. 

Many people just step all over this handy direction guide on State Street as they try to use their phones to figure out where they are going. While recording here I helped three people with directions and another who asked why I was filming the ground.

Quick Facts for those that don’t like paragraphs

  • OK, here are some quick facts to help you get around Chicago’s super easy address system:

    ·         All addresses start at State and Madison.

           That corner is 0 N., 0 S., 0 E., 0 W.

    ·         There are 800 address per mile. Example. If you are at State and Madison and need to go to 400 N. State it is a half mile walk.

    ·         Odd numbers are on the East side of North / South streets with even numbers on the West side of the street.

    ·         For East / West streets, odd numbers are on the South side of the street, and even numbers on the North side.

    ·         If you are West of Pulaski each mile of streets starts with the same letter so you get one mile of streets starting with K, then a mile of streets starting with L. There are a few exceptions, mostly with the larger more major streets. There are some inconsistencies within the smaller streets as well. For example, you have a mile of streets starting with K but a street named Tripp and Lowell are in between Keeler and Kostner with Kildare separating Tripp and Lowell.

Modes of transportation

  • Feet
  • Bike
  • Driving
  • Bus
  • Boat
  • El
  • Metra
  • Ride Share

Where ya goin’?

I can’t really say one mode of transportation is better than another. It really does depend on what you are doing, where you are going, who you’re with and the weather. If you’re here on vacation with your family you might get around differently than someone who commutes to work every day.

What are my best options?

If you are staying downtown (Loop) and you plan on staying in the downtown area walking is the best way to get around. If you drove in from out of town, leave your car behind and start walking. Honestly, depending on traffic, you might get to your destination quicker, you wont have to hunt or pay for parking, if you are not from here or necessarily comfortable driving in Chicago just walk it. Plus, if you see something cool on the way to your destination you can’t always just pull over, stop and get out with out (parallel) parking the car, paying for parking and that’s if you can find a spot.

I and I’m sure most Chicagoans will say the same thing; most of the time you are going to walk from where you live or are staying, then take a bus or train or both to get close to your destination then walk the final stretch.


I love walking around the city. If you are walking down the street and you pass by a cool store you can just walk right in and check it out. Walking gives you a feel for the city by being surrounded by the sights, sounds and smells. It’s good exercise too. So, if you have a bucketlist of Chicago food and restaurants to check out your’ gonna need to walk that off anyway. 


I can’t say that I bike to much for transportation. For me it’s mostly cruising the 606 to get out of my desk chair and work my muscles a bit differently than skateboarding. I do know lot of people who bike commute to work. It does have it’s challenges and well as benefits. It can be quicker than driving, that’s for sure. If you live here you will eventually get used to weaving in and out of pedestrians and traffic just like driving. On vacation, however, if you are not an experienced urban rider maybe consider another mode of transportation.

If you do want to just take a spin on the 606 or lakefront path you can rent bikes from Divvy. Those you can ride one way and drop off at a station when you are done. Some of the other bikes, such as the two and four person bikes, that you can rent at Navy Pier or the river path are going to have to be returned where you rented them. Seems simple but remember that how ever far you rode in one direction you are going to have to ride back to where you rented the bike. Also, please do not try to ride one of these down the street of river path! I have seen people try. It’s dangerous and will just be frustrating for you and who ever you are with.


Sometimes you will need to drive. For example: When we have some out of town friends or suburban friends and family that want to go to Lincoln Park Zoo, I’m driving. Trying to wrangle six people that don’t know how to use the bus and are not familiar with a urban environment just isn’t worth it. Now if teaching them how to use the bus is on our agenda, well I’m always happy to teach. Instructional videos coming soon!


Some people really hate the bus. Like it’s some kind of second rate mode of transportation. I love it. I get stuck driving a lot so any chance to look out the window and see what I missed while I had to drive is a welcome change. I also use it as a opportunity to be productive. Post some social media, take notes on future projects, return texts and emails…


Chicago has a river running right through it. Appropriately named The Chicago River! Lately the river has been bustling with activity. if you don’t have your own boat and don’t want to pay the high cost of the tour boats (that don’t let you off along the way) take the Water Taxi. The water Taxi is a reasonable price and can get you from downtown to Chinatown. You’ll get some awesome pictures from the river level. Especially if the timing is right going under the El tracks at Lake or Wabash.


Coming soon


Coming soon

Ride share

Coming soon