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Depending on where near Chicago you are there are a few decent roads to ride in Illinois.
If I had an idea if you were north south or west I could offer some nice suggestions.
Northern suburbs head into WI, most any road west of I39 is great! Try the Kettle Moraine area just north of Milwaulkee.
Western burbs not a lot of choices but IL RT 2 from Rockford to Dixon along the river is a nice ride.
If you head south and west to Morris you can take Old Stage Road from Morris to Seneca, runs along the river then IL RT 6 from Seneca to Marsielles and from there take Canal Road to Ottawa. Find Rt 23, cross the river and take McKinnley Road back to the East. Just east of Seneca you think you are entering a factory but just keep going to Buffalo Road, about 2 miles. Turn north (left) and follow that road around along the river back to IL RT 47 on the south side of Morris.
Or before you cross the river on 47 head east onto Pine Bluff Road, take it to I55 and head home or after crossing the river going north on I55 take the first exit and head east some more on River Road. Take the first right and ride through the forest preserve. it comes out on IL RT 53 where once again you can head north for home.
Try those out, if you like them I can suggest a few others as well.
I have not lived in Illinois for years, but I do remember the roads along the Mississippi River near Galena being very nice. IL Hwy 84 comes to mind. If you ever get down closer to St Louis, ride the River Road through Grafton.
I also live in the city and my bread and butter 65-mile ride is up to Kenosha, all interstate but a good ride none the less.
As someone previously mentioned, heading out (north) west through Rockford to places like Galena is a nice poke as well, 100+miles (for me). You've got Dubuque, IA also not too far from Galena. Or once you get to Rockford you can head north into Wisconsin through Janesville and such, lots of lakes and places for a cold one or two, and Madison is also not too far from there.
Dead West, I sometimes get out to Dekalb which for the most part is wide open.
Primarily i stay to the north of the city, b/c going to places like Peotone and Joliet make it a complete nightmare entering the city coming home on the weekends.
Savanna is a fun little town. I like the places downtown also. The L&M Motel is a great place to stay. They will take you in a van to any of the spots and pick you up.
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