Just finished the Chicago Basin 4 (Sunlight, Windom, Eolus x 2).
Hiked in to the Chicago Basin (CB) from the Needleton Train stop after riding the Durango-Silverton narrow gauge from Durango and camped that first night.
0230 start from the CB campsite with headlamp in the dark from the basin and summited Sunlight by 0530, then skirted the basin and did a class 4 scramble up the west side of Windom, down the Windom ramp back to the twin lakes area and up the other side of the basin to Mt. Eolus's direct ridge approach. Back down the Mt. Aelous ridge catwalk and up North Eolus, then back down the boulder field from the Eolus pair, into the basin and back to the campsite. ~ 12hrs, took my time and many breaks, clouds and a little rumbling thunder started to roll in about 1pm, light rain for only about 15 minutes after 3pm.
Not certain what might be helpful here so here are a few tidbits.
If you hike all the way in to the twin lakes on the first day, you'll at least know what that hike looks like before you climb the 14ers.
I camped in the Chicago Basin pretty far down and had to hike up to twin lakes in the dark the next morning which was a little confusing b/c the trail has a few parts that need daylight or an excellent map study to follow it across some granite rock stretches early in the hike.
I didn't want to go up and down the Windom ramp approach from Sunlight b/c it would have been boring to me, so I decided to climb the class 4/5 west side of Windom close to the ridge on the way up and then take the standard ramp approach on the way down. It was fun for me, but don't do it if you don't have experience climbing, it's more technical than a novice would be comfortable with. After those two summits I was tired, but the Eolus boulder field approach was very easy (even though I hate boulder fields), there's been a ton of work done on this path and it's basically a stone staircase that's easy to follow all the way up to the summit approaches. I took the ridgeline catwalk approach to Mt. Eolus b/c I wanted to get the most difficult of the two out of the way first and I didn't want to mess around with trail-finding along the side of the slope to figure out how to get to the summit. The ridgeline is very straight-forward and relatively easy to climb. I also wanted to get the most difficult of the two Eolus's out of the way so that I had an easier final ascent to my final summit (North Eolus) at a time in the day when I was low energy and more prone to mistakes. North Eolus was the easiest of all four 14ers and the descent was straight-forward and easy. Off the peaks by 1230, out of the boulder-field by 1pm, back to the campsite by 2-2:30pm-ish, long day, but good workout. Wouldn't have been possible if I hadn't started early at 0230 . . . early start was the key to making all 4 summits possible in one day.