A First-Time Visitor Guide: How to Get Around Downtown Chicago

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As you know, Chicago is a big city.  In a lot of ways, each interconnected neighborhood is like its little town.  And once you’ve conquered and explored downtown Chicago, getting to know the surrounding neighborhoods is going to be a snap.

There are several ways to get around downtown Chicago.  It’s always good to have options, right?  The ways to get around Downtown Chicago that I will be discussing in this article are:

  • Walking
  • Public transportation
  • Water Taxi
  • Bicycle

How to get around Downtown Chicago by foot

The absolute best way to get around Chicago is by walking.  Most downtown Chicago attractions will be within walking distance of your hotel or Airbnb accommodation.

The city of Chicago has put a lot of work into making the city pedestrian-friendly.  And it shows!  Chicago is the 6th most walkable city in America.

Tools such as marked crosswalks, pedestrian signs, pedestrian signals, and countdown timers have been implemented to help protect as you walk along Chicago’s city streets and sidewalks.  So feel free to explore.  Just be sure to do your part by obeying pedestrian signs and crossing only at a marked crosswalk.

A tremendous navigational tool that I highly recommend is the phone app Google Maps.  You can set it for pedestrian directions (as opposed to instructions for cars).  It is an excellent way to get you where you’re going without getting lost.

If you’re not into gadgets or don’t mind getting a little lost, here are some tips:

  • Chicago streets run on a grid system
  • every eight blocks is a mile
  • Lake (Michigan) is east.
  • State Street is 0 east/west, and Madison is 0 north/south.

If you keep in mind where the Lake is in relation to where you’re at, you will never get lost. This tip has helped me many times!

Getting around downtown Chicago using public transportation (bus and “L”)

Chicago has the best public transportation options in the world!

Okay, I’m biased and overstating it a bit.

But seriously Chicago’s public transportation is one of the best.  When I first moved to Chicago, learning to navigate Chicago’s public transit was terrifying.  I’m directionally challenged, so it wasn’t easy.

Luckily, Chicago has updated its public transportation map system in the last 20 years or so.  It’s a lot easier for visitors to get around the city.

And the added benefit is that learning to navigate Chicago public transportation will help you feel less intimidated should you visit other big cities and need to use their public transportation system.

Fares

Fare for buses is $2.25, and for the “L” (train), it is $2.50.  Buses run every 8-15 minutes depending on the route, day of the week and time of day.  Trains run every 8-10 minutes, depending on the time of day.

Fares can be purchased by using pay-as-you-go (mobile banking apps such as Google Pay or Apple Pay) or by buying a fare card at a Ventra Fare machine.  For more information on fares and ways to pay, click here.

To enter turnstile, touch your device or fare card to the reader then enter through the turnstile.  Call me old-fashion (and I’ve heard horror stories when it comes to refunds…why chance it), but I recommend using the fare card option.

For buses – upon entering and touch your device or fare card to the reader. Always board at the front door of the bus. You can also pay cash, but be aware that the Bus driver does not carry change.  You must have the exact amount when paying by cash.

What bus/train do I take?

Not sure what bus or train to take to get to your destination?  Again, I recommend Google Maps, which also has a public transportation option.  Just type in the address or name of the attraction (example, Willis Towers), and it let you know what bus and/or train to take, what stop to get off, and walking directions.

You can track buses and trains schedules by downloading one of many transit apps from Google Play or Apple store.  My favorite is Transit by Transit App, Inc.  It is a great app and can be used in most major cities that have decent public transportation.

Getting around downtown Chicago by Water Taxi

A water taxi is an amazingly cool way to get from one side of downtown to the other and do some sightseeing by boat at the same time.

The Chicago Water Taxi’s routes connect downtown neighborhoods such as the West Loop, River North (seasonal), Streeterville (Magnificent Mile) with neighborhoods just outside of downtown Chicago such as Chinatown (seasonal), and River West (seasonal).

For more information on tickets, routes and schedules, click here.

Getting around Chicago by Bike

Along with being pedestrian-friendly, Chicago is very bike-friendly. Chicago has more than 200 miles of on-street protected,  buffered, and shared bike lanes along with many miles of off-street bike paths (such as the Lakefront Trail).

You can rent a bike and set off on your urban adventure! You can check out prices for a full-day rental through Viator, by clicking here.  The rental comes with a bike, a lock, helmet, and a detailed city map.

Or click here to go to Divvy’s Bike Share Program to rent a bike for the day.

The city of Chicago has its bike map that you can use to get around.  It also gives tips on how to ride Chicago’s streets safely.  To download a copy of the map, click here.

In the rest of this article, I will discuss how to get from the airport to downtown Chicago using rapid transit (“L”).

Chicago has Two Airports

Say WHAT???!!!!

Yes, Chicago has two airports.  When booking your flight into and out of Chicago, you want to choose the best option when it comes to airports.

To learn more about how to make the airport choice that works best for you, read my article, “Flying Into Chicago: What Airport Do I Fly Into?”.

Things to consider when choosing which Airport

If you don’t feel like clicking to another article (hey, I get it), here’s a summary with recommendations –

  • If you’re flying from another country (no matter if you’re staying downtown or not) – choose O’Hare Airport…well, you don’t have a choice.
  • If you’re going to be staying downtown Chicago and you live near an airport that Southwest Airlines flies out of –  choose Midway Airport.  Note: Delta Airlines have limited flights to Midway Airport
  • If you hate Southwest Airlines or fly out of an airport that Southwest doesn’t services – choose O’Hare Airport or fly Delta Airlines (limited service) into Midway

Other things to consider when choosing an airport

  • Midway Airport is the closes airport to downtown Chicago
  • O’Hare Airport is very far from downtown Chicago
  • Chicago has horrible rush hour traffic – allow extra time if you’re taking Uber, Taxi or shuttle
  • Public transportation is the fastest and best way to get back and forth; to and from airports

If I have confused you, click here to be taken to flychicago.com.

 

airport terminal

How to get from Midway Airport to downtown Chicago

The Orange Line “L” is the fastest (25 minutes) and the cheapest way ($2.50) to get from MDW airport to downtown Chicago. It operates from 4 AM – 1 AM every day (for frequency and times, click here).

Fares can be purchased by using pay-as-you-go (mobile banking apps such as Google Pay or Apple Pay) or by buying a fare card at a Ventra Fare machine.  For more information on fares and ways to pay, click here.

The Orange Line Station is connected to Midway Airport.  Follow the signs that say “Trains to the City.”  Purchase a fare card (re-loadable) at the Ventra Fare Machine.  Touch the fare card to the reader then enter through the turnstile.

To use Pay-as-you-go (Google Pay or Apple Pay) to enter turnstile, touch your device to the reader then enter through the turnstile.  Call me old-fashion (and I’ve heard horror stories when it comes to refunds…why chance it), but I recommend using the fare card option.

Once you board the train, you will want to exit at Roosevelt or any stop after Roosevelt.  The stations go  something like this:

  • Midway (where you boarded)
  • Pulaski
  • Kedzie
  • Western
  • Archer/35th Street
  • Ashland
  • Halsted
  • Roosevelt (you are now downtown) you can transfer to Buses, Red or Green Line at this station

*the L continues clockwise around the Loop (downtown) to the following stations:

  • Harold Washington Library/State/Van Buren (transfers to Buses, Brown, Pink, Purple, Blue and Red Lines here)
  • LaSalle/Van Buren (transfer to Buses – get off here if you need to get to LaSalle Street Metra Station commuter rail)
  • Quincy (Transfer to Buses or walk to Union Station for Amtrak or Metra Station)
  • Washington/Wells (transfers to Buses, Brown, Pink, Purple, Oglivie Metra Station commuter rail)
  • Clark/Lake (transfers to Buses, Brown, Pink, Purple, Blue and Green Lines here)
  • Washington/Wabash (transfers to Buses and Millennium Metra Station commuter rail)
  • Adams/Wabash (transfers to Buses, Brown, Pink, Purple, and Green Lines here)

*the L continues to Roosevelt station and heads to stations westward to Midway

How to get to downtown Chicago from O’Hare Airport

The Blue Line “L” is the fastest (40 minutes) and the cheapest way ($2.50) to get from ORD airport to downtown Chicago. It operates 24-hours (for frequency and times, click here).  Rush hour traffic from O’Hare to downtown can be painfully slow and can take up to hours.  Literally – no joke.

The Blue Line Station is connected to O’Hare Airport.  Follow the signs that say “Trains to the City.”  Purchase a fare card (re-loadable) at the Ventra Fare Machine.  Touch the fare card to the reader then enter through the turnstile.

Fares can be purchased by using pay-as-you-go (mobile banking apps such as Google Pay or Apple Pay) or by buying a fare card at a Ventra Fare machine.  For more information on fares and ways to pay, click here.

To use Pay-as-you-go (Google Pay or Apple Pay) to enter turnstile, touch your device to the reader then enter through the turnstile.  Call me old-fashion (and I’ve heard horror stories when it comes to refunds…why chance it), but I recommend using the fare card option.

Once you board the train (it will say Forest Park on the side of the car), you will want to exit at any of the downtown stops.  If you’re not sure which stop to get off at use, the Google Maps App (make sure you have it set for public transportation) by typing in your hotel, hotel address or accommodation, etc.  The app will give you directions to your destination.

The stations go something like this:

  • O’Hare (where you boarded)
  • Rosemont
  • Cumberland
  • Harlem
  • Jefferson Park
  • Montrose
  • Irving Park
  • Addison
  • Belmont
  • Logan Square
  • California
  • Western
  • Damen
  • Division
  • Chicago (Downtown)
  • Grand (Downtown)
  • Clark/Lake (Downtown)
  • Washington (Downtown)
  • Monroe (Downtown)
  • Jackson (Downtown)
  • LaSalle (Downtown)
  • Clinton (Downtown)

*L’ continues on west out of downtown

 

Conclusion

In this article, I discussed the many ways a visitor can explore and get around downtown Chicago.  Is this is your first time visiting Chicago, I recommend walking as the best way to explore downtown.  But feel free to try out one or more of the other options such as public transportation, water taxi, and biking.

Another thing I address in this article is how to get to downtown Chicago from the airport.  If this is your first time to Chicago you might be surprised to find out that we have two airports; Midway and O’Hare.  The best airport to fly into is dependent upon what is best for you as a traveler to Chicago.

 

 

 

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