How to Get Around Downtown Chicago

With two airports and a world-class public transportation system, getting around Chicago can at first seem overwhelming, but it doesn’t need to be.  In fact what can make it seem overwhelming is actually what makes it so simple…staying on the north side, fly into O’hare.  South?  Then Midway’s your answer.  Regardless the L is just a short walk away.  Confused yet?  Keep reading for the ins and outs of getting around the Windy City.

Getting to Chicago

There are three major ways to get to Chicago.  You can fly, take a train or drive depending on how far you are located and what your plans are.

Planes

If you are over a 4 hour’s drive away I would recommend flying but that’s totally your preference.  

Chicago has two airports, Chicago O’hare and Chicago Midway.  O’hare is a huge airport northwest of downtown while Midway is southwest of downtown and a little easier to navigate.  Both airports have a CTA train directly inside that can take you downtown (more on that below) which I recommend.

Trains

If you are closer than 4 hours and are near a train station I recommend taking a train.  

I really enjoy train travel if the stations are convenient.  Unlike airports, you don’t have to get to the station really early and deal with pre-boarding but you still get the benefit of being able to do whatever you want on your journey.  The trains that will take you into downtown Chicago are Amtrak (long distance), Metra (Illinois/Wisconsin commuter), and the South Shore Line (Indiana commuter).

• Amtrak will take you into Union Station which is located just outside of the Chicago Loop (a commercial area located downtown).  Since it’s outside of the loop it’s kind of in an odd area to be walking around with a suitcase which is why I recommend taking a Lyft to your hotel.
• Metra has multiple stops depending on where in the city your final destination is and where you are originating from, best to check the Metra website for more details. The two stops that are outside of the loop are Ogilvie Transportation Center and Union Station which are about a 5 minute walk apart.  If either of these is your stop then again, I’d recommend taking a Lyft. If you are getting off inside the loop then you have multiple options depending on where your hotel is located.
• The South Shore Line ends at Millenium Station located inside of the Chicago Loop on Michigan Ave and Randolph St. This location is pretty accessible to anywhere you’d like to go in the city.

Automobiles

If you are close-ish and plan on trekking out to the suburbs you may want to drive.

Parking is a hassle in Chicago and in many areas it’s also expensive. I don’t recommend taking a car unless you know you’ll have an inexpensive, easily accessible spot, in which case, congratulations!  With so many transportation options available driving is something I’d rather not worry about, but you do you.

You can also get to Chicago by bus but to be honest I’d rather take a train if I’m close enough that I’m not going to fly. 

Getting Around Chicago

There are 4 main ways to get around downtown Chicago. You can take the “L” or “El” (spelled both ways but pronounced like the letter) train, bus, Lyft, or drive.

CTA L 

I’ve lived in Chicago and New York and I have to say, the L is so much easier to navigate than the subway. If you’ve ever taken the subway then this will be a piece of cake.  It’s nicknamed the L because of the Elevated tracks but just like the subway, there are parts that are elevated and parts that go underground.

To get on the L you’ll need to either use a Ventra card (which can be purchased at a Kiosk) or you can use a contactless credit card at the turnstile.  Most rides will cost $2.50 per ride and there are unlimited passes you can purchase as well. The lines are set up by color and are identified by the first and last stop on the route. There are 8 color lines and they all go downtown.  Usually, the L can be an inexpensive and efficient way to get around. The train’s ETA is updated on Google maps so you can see when the next one will arrive or how long you need to wait.

I mentioned above that the L goes directly into both airports.  The blue line goes into O’hare and the orange line goes into Midway.  Going to the airport the train will say O’hare or Midway, leaving the airport it will say Forest Park or Downtown for you to get into the city.  Taking the train downtown is really common so you should feel totally comfortable doing this. 

CTA Bus

CTA operates a lot of buses on a variety of routes. 

I recommend typing your destination into Google maps and it will tell you which bus numbers you can take. Then walk to the bus stop and wait for it to arrive.  The CTA buses also take the Ventra cards I mentioned above or contactless credit cards. There aren’t Ventra kiosks at the bus stop though so if you don’t already have a card then you’ll have to use contactless or find an L stop to buy a card.  

Sometimes the best way to get across town is a bus as there aren’t many cross-town L’s (especially north or south of the loop).  I’ve found that when I’m on the bus it always takes longer than Google says it’s going to take though because just like cars, the buses have to battle traffic.

Lyft

Sometimes you just don’t want to deal with public transportation and that’s OK.  I recommend Lyft.  

Maybe you’re wearing heels, maybe it’s late and you don’t want to wait 15 minutes for the train or maybe there isn’t a convenient stop…it really doesn’t matter the reason for not wanting to take public transportation.  Luckily Chicago is pretty accommodating to Lyft and you can hail one at either airport (although that can get pretty pricey) and they are plentiful downtown.

Taxi’s are available in Chicago but I’ve found when I’ve taken them recently that the drivers aren’t any more knowledgeable than Lyft drivers (which used to be a benefit).  I also prefer not to have to talk to the drivers to tell them where I’m going and also figuring out the whole payment thing is a pain.

Car

If you’ve decided to drive to Chicago then you are probably planning on driving around Chicago as well.  

There is some street parking and you might be lucky enough to find it.  Most downtown is metered and while you can pay the meter like back in the day there is also an app for the phone called ParkChicago.  I highly recommend getting this and setting it up before you try to park. It’s easy to pay for your parking on the app and if you are out and about you’ll get a notification when the time is expiring and you can extend your time.  Parking tickets in Chicago are no joke, I’ve let my time expire by 5 minutes before and gotten a $50 ticket.  

Certain streets are permitted parking only during certain times (usually overnight into the morning) so if you want to park there a resident will have to give you a daily pass.  They are inexpensive but don’t let that fool you, if you don’t have one don’t be surprised to wake up with a city parking ticket.

If there is no street parking then there are several garages to choose from but they can get expensive which is why I don’t generally recommend it.  If you are going that route then I like to use the SpotHero app to find a good deal and prepay.

Now that you know how to get around, check out these other Chicago guides:

• Best Hikes Near Chicago
• Coolest Chicago Hotels
• Where to VRBO in Chicago
• 3 Day Chicago Itinerary for Spring & Summer