Resources for Chicago Transportation, Tolls & Parking in the City -StepintheChi.org

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CHICAGO WEATHER TODAY. MAYBE THE TIME TO GO IS NOW.

A popular question from steppers about traveling to Chicago is how to get around and ideas for Chicago transportation. Do I need a car? My answer every time is an equivocal, “Yes!” In Chicago, there is so much to do. To make the most of the time on your weekend or however long your visit having access to reliable transportation is important.

Ride Options, Safety, and Stepper Set Hopping in Chicago

“HEY! DIDN”T I JUST SEE YOU AT THE 50?” SHE SAID AS I WALKED INTO THE BLUE NOTE.

Chicago offers plenty of transportation options, but getting between stepper sets can still be a challenge. With two to three stepper sets or parties happening most days, they’re often spread out across the city, making moving around by rideshare more expensive. For example, traveling the 20 miles between the Blue Note and the 50 Yard Line can cost at least $30 by Uber on a good night without surge pricing. While public transportation runs late in this city that never sleeps, renting a car or carpooling with other steppers can be far more convenient and cost-effective. Many steppers love to “set hop,” spending a couple of hours at one spot before heading to the next stepper set, and having personal transportation allows you to maximize your time on the dance floor in different places without breaking your travel budget.

Uber and Lyft Rideshare Transportation options

Chicago Rideshare -Uber, Lyft

Relying on Uber or Lyft can get expensive, especially with fare surges during after-work hours—just as steppers are gearing up to hit the dance floor. Late-night travel also comes with safety risks, when leaving the set to head home after 10 p.m. or even as late as 2 a.m. While rideshare companies like Uber and Lyft provide safety information on their websites to help protect riders and drivers, it’s important to stay mindful of your surroundings. With stepper sets often 10 miles or more apart, particularly when traveling from the South Side to the West Side, personal transportation offers a safer, more cost-effective, and convenient option for getting around.

Public Chicago Transportation by Bus or Train

Chicago has a vast public transportation network compared to some cities by bus and/or train. Find out more about Chicago Transit Authority(CTA) on their website. It is easy to navigate the CTA using the Google Maps App on a mobile phone to find the exact bus and train routes to get from Point A to Point B. If you plan to spend all your visit in the city, buy a 3-day or 7-day CTA pass to get you everywhere you want to by train and bus.

Chicago Car Rentals for Transportation Tile

Car Rentals in Chicago

If you’re not moving around with Chicago friends, rent a car. Most rental car companies offer lower rates at O’Hare than at Midway Airport. But, it is more convenient to fly into Midway – the airport on the Southside. Go figure! All major car rental companies are available at both Chicago airports. Shop around for the best rental rates.

Turo for Chicago Transportation

For an alternative to traditional rental car companies, consider using Turo. This app and website allow you to rent personal cars and vehicles directly from the owners, often providing a wider range of vehicles and flexible pricing. It’s a great option if you’re looking for something more unique or cost-effective than a standard rental. Whether you’re sticking with a commercial rental or giving Turo a try, you’ll have plenty of ways to get around Chicago on your own schedule.

Before Driving in Chicago

Stay alert! Be smart! Have local Chicago stepper friends and connections help you navigate different areas of the city. We know everyone wants to discover new sets and places to eat. If you choose to drive in Chicago, here are some basics to learn and know about parking and tolls.

Parking

If driving in Chicago, brush up on your parallel parking skills for street parking. Read all parking signs for reserved parking, street sweeping schedules, snow plowing, and resident permit parking. They are EVERYWHERE it seems. Learn more about parking online at the City of Chicago. Check the end of the streets for these warnings and avoid parking violations. Observe the street signs and they mean all of them. Parking violations can result in your vehicle being ticketed, booted, or even towed. They will give you a ticket for parking on a crosswalk. Available street parking on the Southside is limited due to crowding. You can spend 15-30 minutes or more driving around to find a spot after leaving the steppers set late at night.

Tolls

There are toll roads in Illinois that may save you a couple of highway miles here and there. I will tell you though that a few locals I have driven around with take the local roads and get to places just as fast. If you fly into O’Hare there is a $1 toll just to get out of the airport. Sigh! Most rental car companies offer toll passes, and I think they are expensive. You have an option that can save you the toll pass usage fees that rental companies charge. In Illinois, you can go online and pay-by-plate using a vehicle lookup within a certain number of days. Learn more about that option online at Illinois Tollway.

Towing and Tickets

If your car has been towed by the city, you can search for your vehicle by license plate on Chicago Police. Towing can cost you $200 or more to retrieve a vehicle. Parking tickets can be paid online.

Downtown

There is a lot to explore in downtown Chicago. If you’re going downtown, parking can be expensive. When checking out the downtown sights in Chicago, you can take the train or Uber/Lyft and move around during the daytime. It saves a grip on $25 parking fees. I never get there early enough to catch a street parking spot.

Potholes

Watch out for potholes. There are a lot of street repairs needed throughout Chicago. The changing weather tears up the streets. Drive cautiously.

Neighborhoods in Chicago

Here is a neighborhood map of Chicago. Frommer’s gives a great breakout and description of the neighborhoods in Chicago. Visit Frommers to learn more about how the locals view and understand the city.

Learn about the Chicago neighborhoods and areas
Know where you are for awareness and safety
Know Chicago the way that locals know the city