Trailhead Apartments Chicago

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Trailhead Apartments Chicago Trailhead on the 606 is built for every type of vibrant lifestyle.

Featuring 109 apartments, a gym, amenities deck and lounge, and retail on the first and second floor, with direct access to the 606.

The doctor is IN🩺Our pet costume contest is officially over, and Dr. Frannie, the Dogtor won with 36 votes! 🏆Thank you t...
10/27/2026

The doctor is IN🩺

Our pet costume contest is officially over, and Dr. Frannie, the Dogtor won with 36 votes! 🏆

Thank you to every pet parent who entered and every neighbor who voted. Happy Halloween!

Trailhead’s four-legged residents are dressed to impress—and we need your help choosing a favorite! 🎃🐾Swipe through the ...
10/19/2026

Trailhead’s four-legged residents are dressed to impress—and we need your help choosing a favorite! 🎃🐾

Swipe through the contestants, then comment your favorite pet’s name to cast your vote. 🏆

The winner will be determined October 25th.

One of the best seasons in Chicago officially starts today. Happy first day of fall from the Trailhead Team! 🍁🚴🍂
09/22/2026

One of the best seasons in Chicago officially starts today. Happy first day of fall from the Trailhead Team! 🍁🚴🍂

A 93 Walk Score means your car is about to get very comfortable. A Walker’s Paradise where Bucktown, Wicker Park and Log...
09/09/2026

A 93 Walk Score means your car is about to get very comfortable. A Walker’s Paradise where Bucktown, Wicker Park and Logan Square meet. 🚶‍➡️

The 606 called. It wants you closer.  🚴 Studios + one bedroom apartments are currently available at Trailhead, inquire f...
08/24/2026

The 606 called. It wants you closer. 🚴 Studios + one bedroom apartments are currently available at Trailhead, inquire for more info!

Home has entered the chat...🏡 💬 🚴‍♂️
08/11/2026

Home has entered the chat...🏡 💬 🚴‍♂️

Five reasons to love living at Trailhead... and honestly, we could've kept going.Find your next home on the Trail. 🚲
07/14/2026

Five reasons to love living at Trailhead... and honestly, we could've kept going.

Find your next home on the Trail. 🚲

Rarely available. 🏡 We currently have one 2-bedroom, 1.5-bath townhouse, giving you a unique opportunity to enjoy two le...
07/06/2026

Rarely available. 🏡 We currently have one 2-bedroom, 1.5-bath townhouse, giving you a unique opportunity to enjoy two levels of living, all just steps from the 606.

Inquire for more info!

There’s no better place to spend the Summer Solstice than right here at Trailhead! Perched right along The 606, where bi...
06/21/2026

There’s no better place to spend the Summer Solstice than right here at Trailhead! Perched right along The 606, where biking, running, walking, and city living all come together in one of Chicago’s most active neighborhoods.

The kind of studio apartment that changes your mind about studios.Find your next home on the trail. 🚴🏡
06/11/2026

The kind of studio apartment that changes your mind about studios.

Find your next home on the trail. 🚴🏡

Address

1744 North Western
Chicago, IL
60647

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