I've arranged the following reviews in two groups: First east-west routes, then north-south routes. East-west routes are arranged north to south with sub-segments ordered west to east. North-south routes are arranged west to east with sub-segments ordered north to south. Most of these reviews date from 1997. I'm adding review dates for newer reviews.
A lot of stop signs, but clear smooth pavement and low traffic.
The pavement is smooth, the road is clear and traffic is low. I felt a bit uncomfortable with some of the people hanging out near an elementary school I passed along the way (people carrying 3 foot lengths of two-by-four do that to me), but otherwise it's OK.
Ignore the bicycle federation's recommendation to stay on Augusta and then take Sacramento to Grand. I think they were on drugs when the drew that part of the map. It's much easier to go straight to Grand from Augusta. Traffic is a bit more bothersome on Grand, and the road condition is less than I'd like, but it's the most direct route into the city at this point. The Western Avenue Metra station is south on Artesian from Grand, but probably not a safe place to leave your bike from what I've heard.
Not too bad. I wish that Chicago would make bike-friendliness on Ogden a priority. Aside from the nasty cut off lane for the Ogden West to Washington West transition, traffic flow isn't too much of a problem.
If you're heading to the loop from Grand, this is a decent route, but not the best. There's something about the railway underpass that bothers me, but I can't put my finger on it.
Completely unridable. The road condition makes this more equivalent to riding a dirt bike trail than a road. Add in road hazards and Cermak is by far preferable.
A joy. Freshly repaved (is this in the works for Roosevelt further East?) with marked bike lanes that extend all the way to the intersections. The view from the long bridge over the south loop switchyards (Union and LaSalle stations) is spectacular. Easily the best entry into the south loop for bicyclists. Traffic is a bit heavy near the Dan Ryan interchange, but it's not unbearable. Where there are local lanes (Halsted West), be aware that the local lanes have different signals that will leave you standing around with nothing to do. Watch the center signal instead and avoid left turners crossing your path.
Unridable. Probably the worst pavement condition I've encountered and road hazards galore. One gets the sense that the city has abandoned this stretch of Ogden completely. Avoid the local lanes entirely, they're unsafe for car or bike.
The road is in reasonably good repair. There is ample space to the right in an auxiliary lane for diagonal-parked cars to back out, but it's important to keep an eye on cars to avoid being hit by careless drivers. The "el" strip to the north of Cermak may be a tempting route, but the pavement is in poor repair and there are no signals at the major streets.
The road continues to be in good condition here, although road hazards are sometimes distressingly frequent (but are usually cleared within a week or less). West of Ogden, Cermak is a boulevard and a pleasure to ride along. East of Ogden, it's a fairly insignificant street with little traffic. The road condition tends to be a bit worse on the Ogden-Burlington stretch but is still quite ridable on a road bike.
The ride through Pilsen is quite nice. The road is generally in good shape and traffic is not too bad. A nice alternate is to take a jog north to 21st street at Western. Traffic is low, and the raised streets/sidewalks of the neighborhood are clearer as you ride through this mixed residential/commercial neighborhood.
An industrial neighborhood, frequent rail crossings can be a challenge to the bicyclist. Cermak east of Halsted is under construction and unridable. Avoid the car-detour of 18th and either go south to Archer or north to Roosevelt to proceed east (or approach from the west). If you're heading to the loop, it's much better to take Ashland to Roosevelt and Roosevelt in.
More traffic, fewer stops. It balances out to about the same speed as Ridgeland.
A good ride with not too many stops. While Oak Park has fewer stops, it also has more traffic so the average speed possible probably averages out to about the same level. Crossing 39th from either direction is problematic.
A decent enough route, although the long unlit underpass under the Burlington makes it less desirable than Ridgeland for that stretch. At night, it's the best north-south route in the area, well-lit and with little travel. The tunnel is lit as well making it less of a problem.
Why this was suggested as a bike, route I don't know. The road condition is poor and traffic is nasty. The bridge of Ogden and the Burlington is too busy and filled with road hazard to be fun. I'd probably prefer Austin to Laramie. On the other hand Laramie would be preferable to Cicero and Central doesn't cross the Burlington.
Aside from a stretch under the Burlington where the street is being resurfaced, this is probably the best connector between Cermak and Roosevelt. Smooth pavement, no road hazards and decent traffic. Plus it comes just in time to avoid the nasty pavement on West Roosevelt.