There appear to have been three main drivers for this project:
• Financial: The main driver appears to have been the desire for asset maximization by the City of Chicago and the opportunity to monetize an existing infrastructure asset to help address budget deficits, although the project does remove future revenue for the City from the road. The proceeds from the project were used as follows:
| Use of proceeds | Amount |
| Refund outstanding Skyway bond principal and interest | US$453 million |
| Retire a proportion of outstanding General Obligation debt | US$392 million |
| Permanent operating budget rainy day fund | US$500 million |
| Eight-year capital budget and operating budget stabilization fund | US$475 million |
| TOTAL | US$1,820 million |
Source: Crain's Chicago Business, November 2004.
Upon completion of these disbursements, Moody's upgraded the City's overall bond rating a notch to Aa3.
-When the City started the competitive process in 2004, they knew that the road was in good condition, there was an established track record of traffic volume, and a long concession period was on offer. All these factors were likely to attract significant interest from private investors.
-The three bids received in October 2004 ranged from an upfront payment of US$505 million to the US$1.82 billion bid by the SCC.
• Operational: The project entailed the divestiture of an asset that the City regarded as non-core and was underpinned by the belief that an experienced private-sector operator would run the toll road more efficiently than the City could. One of the first things the SCC did was to install automatic tolling systems.
• Political: The number of union workers working on the toll road was small (about 100), therefore there was little union protest as these workers were mostly retained or relocated to other city departments. Also, the potential toll-rate increase backlash would be geared more toward the private-sector operators than toward the incumbent political leaders. As a result, the potential political opposition has been minimal.