This route consists of four main roadways: the Jane Addams Memorial Tollway, the Kennedy Expressway, the Dan Ryan Expressway, and the Chicago Skyway.
Jane Addams Memorial Tollway:
Kennedy Expressway:
I-90 alone:
Approaching the Loop from the Kennedy Expressway EB.
I-94 joins I-90 eastbound, and I-94 departs from I-90 westbound. The Edens Expressway which carries I-94 begins/ends here.
I-90/I-94:
Dan Ryan Expressway (I-90/I-94)
This tangle of ramps is the Circle Interchange / Jane Byrne Interchange, recently reconstructed. A prime example of a turbine interchange.



I-90 joins the Dan Ryan at the end of the Chicago Skyway westbound.
Eastbound, I-90 departs from the Dan Ryan for the Chicago Skyway.
Chicago Skyway:
Interesting situation: The Chicago Skyway was always part of I-90. However, from 1999 to 2022, Chicago did not sign the Skyway as I-90, but rather as TO I-90 because CDOT assumed I-90 was not official in this area, even though IDOT and the FHWA have acknowledged the Skyway as I-90. CDOT now places I-90 shields on overheads for the Skyway.
There are also no exits until after the toll plazas in each direction. This is because of an interesting legal quirk where Chicago could fund toll bridges, but not toll roads, at the time the road was built.

First things first. Why are you SCREAMING on this overhead?
These large flyover ramps from the Chicago Skyway to Stony Island Avenue were built as part of the cancelled I-494 freeway in Chicago, which would have used Stony Island Avenue, an upgraded Lake Shore Drive, and Ohio Street.

I have a few things to say here. That should be a blue banner above the interstate shield. Also, why are you using a three-digit shield for a two-digit interstate?
The toll plaza for the Chicago Skyway.

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