Heading to the Windy City for work or vacation?

Before you head out to find the city’s best deep-dish pizza, you may want to get familiar with how to navigate Chicago tolls.

Chicago has five major tollways that are all part of the Illinois Tollway System. Before we look at these roads, let’s see how to pay Chicago tolls.

There are three main ways to pay for toll roads in Chicago. An app like Uproad is the most convenient way, and it will ensure that you won’t miss a toll payment ever again.

Here’s how to pay for Chicago toll roads:

1. Uproad
   The simplest and most convenient way to pay for Chicago tolls. All you need is your phone!
   Download the Uproad App for your iPhone or Android, and you’ll be navigating your vehicle around those Chicago skyscrapers in no time.
   Uproad allows you to pre-load your account balance to automatically pay for tolls as you drive. With the app, you can calculate costs before you travel and track usage and expenses on the go.
   But most importantly – you’ll avoid toll fines and late penalties – so you can save those $ for more Chicago pizza!
2. Transponder
   Another way to pay for Chicago tolls is with a transponder.
   Both I-PASS and E-ZPass transponders are accepted on the Illinois Tollway. If you don’t already have a transponder and are heading to Chicago soon, then we would certainly recommend downloading Uproad instead. Ordering and setting up a transponder can take some time.
3. Pay-by-Plate
   Missed a toll because you didn’t have the Uproad app?
   Pay-by-Plate allows you to pay up to 14 days after a missed toll. Head here to pay any unpaid Chicago tolls. And remember to download the Uproad app to make life a whole lot easier!

Note: Cash is no longer a payment option on the Illinois Tollway System.

Now that you know how to pay for tolls let’s look at what toll roads you might drive on when you’re exploring the iconic neighborhoods of Chicago.

Also known as the Elgin-O’Hare Tollway, the 390 is an expressway that runs 12 miles through the Western suburbs of Chicago.

The road begins in Hanover Park and heads east through Schaumburg, Roselle, and Itasca. The expressway is currently undergoing construction to extend through to the Western side of O’Hare Airport.

The Jane Addams Memorial Tollway is part of Interstate 90 and creates a direct link between Rockford and the Chicago Metro Area, including O’Hare International Airport.

The road is named after a Chicago legend who spent 46 years in the city, dedicating her time to assisting poor immigrants and fighting for important issues like child labor laws and for women’s rights to vote.

The Tri-State Tollway or Interstate 294 runs between Lansing and Deerfield, avoiding most of the city. It was originally designed as a bypass route around Chicago but is an important route connecting O’Hare International Airport with the rapidly developing outer suburbs.

The Ronald Reagan Memorial Tollway is a 96-mile stretch of road connecting the Eisenhower Expressway to the Illinois Tollway at Dixon.

As one of Illinois’s busiest roads, the tollway sees over 240,000 vehicles daily.

The Veterans Memorial Tollway is situated in the western and southwest suburbs of Chicago. The tollway runs from New Lenox north to the I-290 in Itasca.

Download Uproad via the Apple Store or Google Play and get exploring the great city of Chicago