Downtown Chicago: Getting Around the Windy City

When planning a trip to downtown Chicago, it’s important to plan ahead. And a big part of the planning is deciding A) how you’ll get there and B) how to get around once you’re there. Below you’ll find some tips and resources that will help you decide what works best for your situation.

Getting to Chicago

There are two main ways to get to and from Chicago. Driving yourself or taking a train. When deciding your budget for your getaway, consider all possible expenses.

  • If you drive yourself, take this into consideration. How much gas will you need? Will you park your vehicle at the hotel and leave it there, relying on public transportation or Uber/Lyft? Will you drive yourselves to your destinations, considering that parking is expensive most places and sometimes finding parking is a challenge? It isn’t impossible to drive your own vehicle to and from Chicago, but staying downtown does require some extra planning!
  • Consider taking the Amtrak to downtown Chicago. While you may not save much money, the ride is relaxing and you don’t need to worry about driving in heavy traffic. Rates can be quite inexpensive, as cheap as $19 each way per person, depending on the travel dates.

Amtrak

  • Go to the Amtrak website and sign up to receive offers. They will sometimes offer promotions at certain times of year, which include percentage discounts as well as an occasional promotion where a second traveler rides free or at a lower rate.
  • Fares tend to be lower earlier in the morning and later in the evening.
  • Get to the train station early enough so that you can find parking, at least 30 minutes before departure. If it’s a popular travel day, the parking lot at the Springfield station will get full. There is a parking garage across the street, if the lot is full. Be sure to get a parking pass inside the station if you park in the lot.
  • Most trains have power outlets and WiFi,

Union Station – Chicago

  • When you get to Union Station, your next stop should be the exit where rideshares pick up, such as Uber or Lyft, or the Ventra vending machines. These machines will sell CTA (Chicago Transit Authority) passes that get you access to the “L” trains (above ground and subway) and buses.
  • Union Station has a food court with several options, ranging from Starbucks to McDonalds.
  • The lines to return home can sometimes be long, so be sure to arrive at least 30 minutes prior to departure.

Baggage Handling and Storage

  • If you’re arriving downtown in the morning, you’ll need to decide what to do with your bags.
  • Check with your hotel to see if they will stow your bags for you until you can return to the hotel for check in. Most will do this for free or a nominal charge. Go straight from the train station to your hotel and unload your bags, so that you aren’t loaded down while exploring the city!
  • Union Station will store your bags for $10 each. Consider using this option if your initial Chicago stops are near the station.
  • There is a service called Luggage Hero, which allows you to pay a fee to a business to store your bags.

Public Transportation

  • There are a few different public transportation options available – the “L” (elevated trains and subways) and buses.
  • Tip: The CTA (Chicago Transit Authority) has a new “pay as you go” option for contactless card holders (Apple Pay, Google Pay, etc.) and machines are available on buses and at the L gates
  • Click HERE to learn more about CTA fare options.
  • Us the CTA “Plan a Trip” to help get you the best route to your destination.

Rideshares

  • Sign up for Lyft and Uber apps, as both will give you a free first ride and send occasional promotions.
  • Check your destination on both apps, because there can sometimes be a noticeable difference in fares.
  • Both apps will ask you to “drop the pin” and mark where you are currently located. Drop this pin carefully, because cell service can be bad in the city sometimes and place your location in a different spot. 
  • Use caution with rideshares. Even though rideshares are a convenient way to travel, and normally very safe, it’s always important to be aware of your surroundings. Both apps will give a description of the driver – name, picture, license plate, and make/model of their vehicle. Be sure to confirm the license plate before entering their vehicle and do a verbal confirmation once inside. 

Parking

  • Check with your hotel ahead of time to determine their parking fees. Almost all downtown hotels will charge a premium rate for parking at or near their location.
  • Attractions and museums will all charge a fee for parking as well. Consider Ubers or taxis between sites to avoid additional parking fees.

Travel Resources

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