(WINTER) HOLD ON! If you don't have much high-elevation, winter climbing experience, be careful in your planning and take a partner. Even the "easy" 14ers (Quandary, Sherman, Grays & Torreys) can be deadly in winter.
Drive to Durango and follow signs to the Durango and Silverton Narrow Gauge Railroad. It's near McDonald's and has a large parking area nearby. Buy a ticket for the train that stops at Needleton and ride the train 2.5 hours (~30 miles) to the Needleton stop. The train will drop you off next to a suspension bridge that crosses the Animas River. From here, it's a 6 mile hike to reach Chicago Basin. Note: you can also take the train from Silverton and be dropped off at Needleton.
To reach Chicago Basin, use the Approach Page. From your camp in Chicago Basin, hike northeast toward the end of the basin on the great trail - Photo #1. Near 11,200', turn left toward Twin Lakes at a signed junction - Photo #2. This trail is used to reach Windom, Sunlight, and Eolus. Continue up through the forest to an area where the trail is a bit difficult to follow over and around some rock slabs - Photo #3. Near 11,400', leave the trees where you have a great view of the two streams that flow down the slope below Twin Lakes - Photo #4. Follow the trail north up the slope and cross the first stream at 11,700' - Photo #5. Immediately after the crossing, climb steep terrain for 300' before the trail angles right and the slope eases. Continue northeast to the second stream crossing before 12,300' - Photo #6. Cross to the east side and again, turn left and climb steeply up the slope. About 200' after the crossing, the slope rolls over and you arrive at the south end of Twin Lakes (~12,500').
Your next goal is to hike around the first lake and continue east. If there is a lot of snow in the area, the easiest way to do this may be to hike around the left (west) side of the first lake and turn right to cross east between the two lakes. When there isn't too much snow, follow the trail around the lake (Photo #7) and up through the rocks - Photo #8. At 12,600', reach the base of a headwall that separates you from the upper basin between Sunlight and Windom. Water is usually running down the center - Photo #9. From here, there are several ways to reach the upper basin. Windom (not visible) is up to your right, so you don't want to climb the left side of the headwall. Follow cairns and trail segments up the right side. Reach the upper basin at 13,000' where there's a great view of the remaining route - Photo #10. In early summer, there may be a lot of snow in the area. Continue east into the basin for a bit, turn right, and locate cairns and/or trail segments that angle up toward a saddle seen in Photo #10. The area is rugged and there are several ways to reach the saddle. Taken from the north, Photo #11 is another view of the slope leading up to the saddle, and Photo #12 shows some of the rock en route. Climb southeast up the slope to reach the 13,250-foot saddle.
From the saddle, 800' of climbing remains up Windom's West Ridge - Photo #13 and Photo #14. The trail pretty much ends here because the ridge is mostly rock. From the north, Photo #15 shows the profile of the entire ridge. Mostly along the left side of the ridge, follow cairns to a small notch at 13,800'. From here you cannot see the summit and the remaining rock gets larger and a bit more difficult to negotiate. Near 13,900', the route is well on the left side of the ridge as you approach the top - Photo #17. Just before the summit there's a small notch in the ridge that allows easy access to the south side - Photo #18. Turn right through the notch, drop a bit, and scramble up to the summit - Photo #19.
There are many dispersed camp sites between 10,800' and 11,100' in Chicago Basin. Some people set up a tent along the trail. The creek provides plenty of water for filtering. IMPORTANT: This route enters the Weminuche Wilderness area. Wilderness areas have special regulations and restrictions for party size, dispersed camping, campfires, etc. Also, dog owners should read the wilderness information carefully because some wilderness areas prohibit dogs to be off-leash and/or limit how close dogs can be to lakes and streams. If you have questions about the Wilderness area, please contact a U.S. Forest Service office for the National Forest(s) listed above.