"Chicago Skyway" Top 5 Page for this destination Driving/Parking Tip by Dabs

Driving/Parking, Chicago: 56 reviews and 48 photos

If you are heading into/out of Chicago via the Indiana Toll Road, you will spend a portion of your trip on the Chicago Skyway. As the price keeps rising and rising and rising, I'm less inclined to use this to get to and from home to Chicago than Highway 41 which eventually merges into Lake Shore Drive. If I'm not in a real hurry, I almost always avoid the Skyway now.

If you do drive it, watch out for the ever present Chicago Police Department writing tickets to speeders, it is practically guaranteed that you will see one during your trip. They lurk on the on ramps, at the bottom of hills and right before the toll plaza when the speed limit drops dramatically so you'd be advised not to go too fast.

And if you are unlucky enough to be continuing on to the Indiana Toll Road, you will get hit within a few miles with yet another toll.

In 2004, the City of Chicago agreed to sell the Skyway and the toll, which had been $2 since 1993 rose to $2.50, then to $3, the to $3.50 and is currently $4 and will likely continue to rise as the agreement allows for a series of increases up to $5 by 2017. You can use your Illinois I Pass, Indiana I Zoom or the EZ Pass (used in northeast US states) to pay the toll on the Skyway but there is no discount over cash like there is on the Indiana and Illinois toll roads. At least you avoid the long cash lines!

Mode: TO
Type: Car/Motor Home

Review Helpfulness: 4 out of 5 stars

Was this review helpful?

  • Updated Nov 17, 2013
  • Send to a Friend
  • Add to your Trip Planner
  • Report Abuse


Dabs Lives Here!


“Never put off til tomorrow what you can do today”

Online Now


Top 1,000 Travel Writer
Member Rank:
0 0 0 1 5
Forum Rank:
0 0 0 2 1

Have you been to Chicago?

  Share Your Travels