Overview
Chicago Peak rises just north of Imogene Pass on the ridge toward Tomboy Peak and T 5. Newer survey data added 6 feet. From the top of Imogene Pass it is an easy ridge walk; this page uses the Tomboy trailhead on the Telluride side.
You go up the rocky basin north of the trailhead to Tomboy Peak, return to the saddle east of it, and climb big boulders to reach Chicago's north ridge. Then it is an easy stroll to the flat top. It is Class 2+ and very rocky. Following the ridge straight from Chicago over to T 5 is very hard.
The loop over both peaks is about 4.4 miles with roughly 2,550 feet of gain. Mileage and gain are our estimates.
Plan of the day
By 7 a.m.
Be on Tomboy Peak by 11 a.m.
The big boulder field between the saddle and the ridge crest.
Easy. Everything goes through the same saddle.
Snowmelt early in summer only. Bring what you need.
Getting to the trailhead
Imogene Pass/Tomboy
This trailhead is on the Imogene Pass road (Forest Road 869) near the old Tomboy Mine, between Telluride and Ouray. You need a 4WD with good clearance from either side. The road is easier than Black Bear Pass, but don't underestimate it: local jeep clubs rate it 4 to 4.5 out of 5, with rocky ledges, tight turns and narrow shelves with drop-offs. Short vehicles do best; skip long-bed pickups. Conditions change, so check before you go.
From Telluride (shorter): Highway 145 becomes W. Colorado Ave. in town. Turn left on N. Aspen St. for 2 blocks, right on W. Galena St. for 1 block, and left on N. Oak St. for 1 block. The dirt Tomboy road leaves on the right. Climb it slowly for 3 to 4 miles to where a side road branches left, at about 11,300 feet, and park. Just past here the main road crosses a creek and reaches the Tomboy ruins.
From Ouray (longer): go south on US 550 about 0.4 mile to the first switchback and turn right on the Camp Bird Road (County Road 361). Near 5 miles, turn onto the signed Imogene Pass road. Cross the pass and drive down the Telluride side past the Tomboy ruins; about half a mile beyond them, park where a side road angles off to the right. Angel Creek and Thistledown campgrounds are on the lower Camp Bird Road (watch for private land). On the Telluride side, the town park campground fills fast, so many people sleep in their vehicle near the trailhead or the old Tomboy townsite.
Base towns and camping for this climb
Coming from out of state? See Lodging & Camping for how free camping works, what is closed this year and where to stay.
Before you go
Check these the week of your climb.
Official forecast
The National Weather Service forecast for the summit area, hour by hour. Look for thunderstorm chances and wind above treeline.
NWS point forecast →Directions to the trailhead
Imogene Pass/Tomboy. Road conditions near the trailhead change after storms. Check your clearance and have a backup plan for a lower lot.
Get directions →Roads and highways
Closures, construction and winter conditions on the highways that get you there.
COtrip road conditions →Closures and fire rules
Trail closures, fire bans and other alerts from the Forest Service in Colorado. For the latest on your trailhead, call the local ranger district.
Forest Service alerts →Snow on the route?
From fall through early summer, any snow slope can slide. Check the avalanche forecast before you go.
Avalanche forecast →Cell signal
Most trailheads and many summits have little or no signal. Check coverage near the trailhead and carry a satellite messenger or beacon if you can.
FCC coverage map →