Go through Jackson Park.
That adds a LOT of mileage to the trip.
There is no good somewhat direct route. There is no good even remotely direct route. When I ride to Blue Island I'm already starting near where Damen starts up again (on 47th or whatever) so one route I sometimes take is Damen - > Major Taylor Trail -> Through Beverly - mostly on Longwood. But the Damen stretch can seem menacing/hostile if you are not used to riding through neighborhoods such as Englewood.
Alternatively I meander through the neighborhoods west of Western.
That 15 mile stretch on Western shown on the RideWithGPS map and the section of Archer depicted will be pretty miserable. Some stretches will have a parking lane that may or may not be full of cars, otherwise you are sharing a four lane artery with drivers who are not very accustomed to sharing the road with bikes. (Archer has rush hour parking which makes it somewhat tolerable if you are going in the right direction at the right time. Southwest during the pm rush or northeast in the morning.)
Much depends on how comfortable you are riding in/around traffic, and what your timeframe is. The fastest route is to take Vincennes, in my experience.
If you don't mind traffic, then Halsted to Vincennes to Longwood is a pretty decent route. Halsted has some moments, and I wouldn't want to ride around 63rd street unless I was moving pretty fast, but it's definitely do-able. Longwood is lovely.
Another option would be take King Drive south, past Washington Park, then cut west a few blocks on Marquette to Vincennes. Warning: it's a bit gnarly right around the expressway, but you avoid some of that by taking the side streets. I prefer to turn S. just before I-94, crossing the interstate at 69th, then picking up Vincennes for the ride home. If you haven't already done so, make a point of traveling just a block or so west of Vincennes to check out the Winnecona Parkway (turn west at 76th St, then travel south on Stewart). It's lovely this time of year with all the holiday lights.
Yet another option is to stay on King Drive all the way to 115th. Bike maps/route planners will recommend 111th, but I much prefer 115th. Ride west to Longwood or Vincennes (depending on how far west you live in town), then home. I actually like this route a lot and I feel quite safe on it, even down south in Roseland/W. Pullman. However, I wouldn't want to ride it late at this time of year... like after 7 pm.
MAKE SURE YOU HAVE GOOD LIGHTS! I also recommend a safety vest. You can get good ones from Ikea for $5 or you can buy nice quality (but more expensive) versions at Jebens Hardware.
p.s. Tony Adams: WESTERN is INSANE to ride on the South side!!!!
Thanks for the feedback so far. I am a confident rider, both from a public safety perspective as well as riding on busy streets. Still, I prefer nice and quiet routes
How about this? I combined Mike's and Jane's suggestions. I am familiar with Longwood, but I am not that famliar with crossing the express ways around 67th and Marquette.Is that doable?
Any advice is welcome
Crossing the Dan Ryan at 69th gets my vote of approval. I much prefer it over Marquette.
Out of curiosity, why did you choose to jog over at 81st from Vincennes to Halsted? While 81st has less traffic, the condition of the road through the huge underpass is horrific. Meanwhile, Vincennes has brand new pavement and a beautifully marked bike lane past Simeon and under the trains.
I also would opt for Vincennes from the merge with Longwood at about 122nd St. Vincennes has a nice gentle climb to it and the road surface is substantially better than the alternatives. I would encourage you to take the entire right hand lane while riding there, btw.
For future reference, both the local bridges over the Cal-Sag will be redone and reopened to the public. The Chatham bridge will be redone for pedestrians and cyclists as part of the Cal-Sag Trail (2016-17). Division Street should be reopened to all traffic by next Spring. Once those are open, you could zip down Irving from Vincennes (up by Florence St), cross Burr Oak by Stan's Park, ride south past the hospital, jog east over the train tracks to Chatham, then cross the canal there.
I used to recommend using 81st to cross from Vincennes to Halsted before the viaducts on Vincennes south of 83rd were repaved. Overall conditions on Vincennes are fairly good - most pavement is in good condition, with bike lanes.
I agree with Jane's preference of crossing the Ryan at 69th vs Marquette. Pavement conditions on Marquette are terrible. Traffic can be nasty. I'd avoid it.
A note on Jane's recommendation on Vincennes further south: there is a dangerously angled railroad crossing at 120th. If you are on Vincennes at this point, it's safer to turn your wheel briefly so you cross it at a 90 degree angle (or as close as conditions allow). People I know have crashed and gotten hurt at this crossing.
If you're riding Vincennes, I second Jane's suggestion of a detour via Winneconna Parkway. It really is lovely.
Halsted to Vincennes is good - see previous notes.
Halsted to 47th to Damen is also good - less traffic than Halsted to Vincennes. South of 47th, Damen is relatively quiet.
A pleasant route through Beverly/Morgan Park: At 87th, go south on the Major Taylor Trail. When you reach 91st, turn right and go through the curb cut at the cul de sac west of the Metra tracks. Go uphill on 91st to Winchester and turn left. Follow Winchester to 94th, turn right on 94th, then left on Damen. Damen makes a left-right dogleg at 95th. Continue to 98th, then turn right to Leavitt. Continue south on Leavitt to 105th or 106th, then turn right to Bell and continue south. Bell is good to 119th, though using 115th to cross Western is more pleasant (via cul de sac at Western). Go west to Maplewood then turn left and continue south. This becomes Ann St. in Blue Island. Somewhere before 123rd St., turn right and go one block west to Maple (has an all-important stoplight at 127th - busy truck route) to continue south.
Maple is good all the way to Vermont St., though Greenwood is more scenic south of 127th.
On the northbound, Hoyne/Seeley is a scenic combo through Morgan Park/Beverly, though it requires careful attention at street crossings at 107th, 103rd and 99th.
No matter which way you go, you will encounter some neighborhoods with challenges. That being said, I rarely have any hassles aside from the usual stuff we face in traffic.
Anne, can you be a bit more specific about "challenges"?
Economically challenged areas where there may be lots of vacant lots, boarded up buildings and illicit street corner activity by folks who may not want to be observed.