1744 N. Western Ave

(9)
Verified Listing
From $2,385
  • Studio-3 Beds
  • 1-2.5 Baths
1744 N Western Ave, Chicago, IL 60647
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Floorplans

Updated Today
Efficiency - A10
  • Studio
  • 1 Bath
  • 539 Sqft
Available now
$2,430 Available now
1 Bedroom - 315
  • 1 Bed
  • 1 Bath
  • 925 Sqft
Available now
$3,022 Available now
Townhouse - 102
  • 2 Beds
  • 1.5 Baths
  • 1,666 Sqft
Available now
$4,440 Available now
1 Bedroom - 303, 307, 309, 407, 409, 509
  • 1 Bed
  • 1 Bath
  • 709 Sqft
Available 02/13/2026
$2,385 Available 02/13/2026
1 Bedroom - B25
  • 1 Bed
  • 1 Bath
  • 887 Sqft
Available 01/07/2026
$2,995 Available 01/07/2026
1 Bedroom - B26
  • 1 Bed
  • 1 Bath
  • 925 Sqft
Available 01/07/2026
$3,055 Available 01/07/2026
3 Bedrooms - 523, 623
  • 3 Beds
  • 2 Baths
  • 1,420 Sqft
Available 01/17/2026
$4,440 Available 01/17/2026
Efficiency - 204
  • Studio
  • 1 Bath
  • 441 Sqft
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Efficiency - A2
  • Studio
  • 1 Bath
  • 511 Sqft
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Efficiency - A3
  • Studio
  • 1 Bath
  • 573 Sqft
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Efficiency - A4
  • Studio
  • 1 Bath
  • 590 Sqft
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Efficiency - A5
  • Studio
  • 1 Bath
  • 441 Sqft
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Efficiency - A6
  • Studio
  • 1 Bath
  • 575 Sqft
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Efficiency - A7
  • Studio
  • 1 Bath
  • 573 Sqft
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Efficiency - A8
  • Studio
  • 1 Bath
  • 590 Sqft
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Efficiency - A9
  • Studio
  • 1 Bath
  • 573 Sqft
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Efficiency - A11
  • Studio
  • 1 Bath
  • 501 Sqft
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Efficiency - A12
  • Studio
  • 1 Bath
  • 575 Sqft
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1.5 Bedrooms - 211
  • 1 Bed
  • 1 Bath
  • 869 Sqft
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1.5 Bedrooms - 311 (ARO)
  • 1 Bed
  • 1 Bath
  • 866 Sqft
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1.5 Bedrooms - 411, 511, 611
  • 1 Bed
  • 1 Bath
  • 866 Sqft
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1 Bedroom - 203 (ARO)
  • 1 Bed
  • 1 Bath
  • 709 Sqft
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1 Bedroom - 225
  • 1 Bed
  • 1 Bath
  • 852 Sqft
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1 Bedroom - 305, 405
  • 1 Bed
  • 1 Bath
  • 819 Sqft
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1 Bedroom - 306, 406, 408, 506, 508
  • 1 Bed
  • 1 Bath
  • 708 Sqft
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1 Bedroom - 308
  • 1 Bed
  • 1 Bath
  • 678 Sqft
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1 Bedroom - 312
  • 1 Bed
  • 1 Bath
  • 821 Sqft
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1 Bedroom - 313
  • 1 Bed
  • 1 Bath
  • 924 Sqft
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1 Bedroom - 314
  • 1 Bed
  • 1 Bath
  • 883 Sqft
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1 Bedroom - 317
  • 1 Bed
  • 1 Bath
  • 841 Sqft
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1 Bedroom - 205
  • 1 Bed
  • 1 Bath
  • 801 Sqft
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1 Bedroom - 320
  • 1 Bed
  • 1 Bath
  • 640 Sqft
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1 Bedroom - 322
  • 1 Bed
  • 1 Bath
  • 883 Sqft
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1 Bedroom - 325
  • 1 Bed
  • 1 Bath
  • 852 Sqft
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1 Bedroom - B23
  • 1 Bed
  • 1 Bath
  • 846 Sqft
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1 Bedroom - B24
  • 1 Bed
  • 1 Bath
  • 800 Sqft
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1 Bedroom, B27
  • 1 Bed
  • 1 Bath
  • 624 Sqft
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1 Bedroom - B28
  • 1 Bed
  • 1 Bath
  • 883 Sqft
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1 Bedroom - B29
  • 1 Bed
  • 1 Bath
  • 736 Sqft
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1 Bedroom - B3
  • 1 Bed
  • 1 Bath
  • 692 Sqft
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1 Bedroom - B30
  • 1 Bed
  • 1 Bath
  • 677 Sqft
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1 Bedroom - B31
  • 1 Bed
  • 1 Bath
  • 821 Sqft
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1 Bedroom - B32
  • 1 Bed
  • 1 Bath
  • 841 Sqft
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1 Bedroom - B33
  • 1 Bed
  • 1 Bath
  • 602 Sqft
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1 Bedroom - B34
  • 1 Bed
  • 1 Bath
  • 586 Sqft
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1 Bedroom - B35
  • 1 Bed
  • 1 Bath
  • 584 Sqft
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1 Bedroom - B36
  • 1 Bed
  • 1 Bath
  • 887 Sqft
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1 Bedroom - B37
  • 1 Bed
  • 1 Bath
  • 689 Sqft
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1 Bedroom - B38
  • 1 Bed
  • 1 Bath
  • 841 Sqft
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1 Bedroom - B39
  • 1 Bed
  • 1 Bath
  • 863 Sqft
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1 Bedroom - B4
  • 1 Bed
  • 1 Bath
  • 930 Sqft
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1 Bedroom - B40
  • 1 Bed
  • 1 Bath
  • 933 Sqft
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1 Bedroom - B41
  • 1 Bed
  • 1 Bath
  • 620 Sqft
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1 Bedroom - B5
  • 1 Bed
  • 1 Bath
  • 796 Sqft
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1 Bedroom - B6
  • 1 Bed
  • 1 Bath
  • 925 Sqft
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1 Bedroom - B7
  • 1 Bed
  • 1 Bath
  • 841 Sqft
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1 Bedroom - B8
  • 1 Bed
  • 1 Bath
  • 622 Sqft
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1 Bedroom - B9
  • 1 Bed
  • 1 Bath
  • 800 Sqft
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2.5 Bedrooms - 216
  • 2 Beds
  • 2 Baths
  • 1,168 Sqft
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2.5 Bedrooms - 221
  • 2 Beds
  • 2 Baths
  • 1,222 Sqft
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2.5 Bedrooms - 316
  • 2 Beds
  • 2 Baths
  • 1,191 Sqft
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2.5 Bedrooms - 321
  • 2 Beds
  • 2 Baths
  • 1,222 Sqft
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2.5 Bedrooms - 416
  • 2 Beds
  • 2 Baths
  • 1,189 Sqft
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2.5 Bedrooms - 516
  • 2 Beds
  • 2 Baths
  • 1,191 Sqft
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2.5 Bedrooms - 521
  • 2 Beds
  • 2 Baths
  • 1,222 Sqft
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2 Bedrooms - D1
  • 2 Beds
  • 2 Baths
  • 1,180 Sqft
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2 Bedrooms - D2
  • 2 Beds
  • 2 Baths
  • 1,180 Sqft
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2 Bedrooms - D3
  • 2 Beds
  • 2 Baths
  • 1,283 Sqft
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2 Bedrooms - D4
  • 2 Beds
  • 2 Baths
  • 1,270 Sqft
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2 Bedrooms - 504
  • 2 Beds
  • 2 Baths
  • 1,107 Sqft
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2 Bedrooms - 510
  • 2 Beds
  • 2 Baths
  • 1,265 Sqft
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2 Bedrooms - 610
  • 2 Beds
  • 2 Baths
  • 1,110 Sqft
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Townhouse - 101
  • 2 Beds
  • 1.5 Baths
  • 1,547 Sqft
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3 Bedrooms - 224
  • 3 Beds
  • 2.5 Baths
  • 1,196 Sqft
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3 Bedrooms - 324 (ARO)
  • 3 Beds
  • 2.5 Baths
  • 1,196 Sqft
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3 Bedrooms - 424
  • 3 Beds
  • 2.5 Baths
  • 1,196 Sqft
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3 Bedrooms - 524
  • 3 Beds
  • 2 Baths
  • 1,265 Sqft
Ask for Pricing
3 Bedrooms - 625
  • 3 Beds
  • 2 Baths
  • 1,265 Sqft
Ask for Pricing

Estimated Fees

  • Application Fees: $75 - $500

  • There may be additional unit-specific fees. Please select a unit and move-in date here.

  • One-Time Pet Fees $100
  • Monthly Pet Rent $30
  • Pet Limit 2 allowed. Restrictions apply, contact the Leasing Office for more details.

The fees are estimates and actual amounts may vary. Pricing and availability are subject to change. For details, contact the property.

Please contact us for utility details. Move-In/Administrative Fee: $350.00 (Due upon approval, non-refundable) Application Fee: $75.00 per applicant (non-refundable)
View more

Apartment Amenities

  • Contemporary Premium Cabinetry
  • Premium Wood-Look Flooring
  • Tiled Bathroom Floors
  • Tiled Kitchen Backsplashes
  • Stainless Steel Appliances
  • In-Unit Washer/Dryer
  • Private Balconies*
  • Spacious Walk-In Closets*

Community Amenities

  • Availability 24 Hours
  • Rooftop Lounge & Kitchen
  • Rooftop deck with fire pit & grilling stations
  • On-Site Parking
  • Pet Friendly
  • Recycling
Ready to see this property in person? Contact the property and ask for a private showing!

  • Apartments in the Community: 109
  • Buildings in the Community: 1
  • Number of Stories: 7
  • Year Built: 2021

Luxury living with direct access to the 606. Trailhead is the one and only building with a direct connection to the 606. Every day your possibilities are open with a game-changing connection between your home and your trail. Get out there and own it. A neighborhood close to everything. Your home should be your escape from the everyday and your launchpad to whatever the day has to offer. As an entirely walkable, accessible, and connectable place, Trailhead on the 606 is built for every type of vibrant lifestyle. Energize your routine. Step up your game on the trail or in the fitness room. Reward yourself with some time basking on the rooftop or enjoying a fire on the amenity terrace. No matter what your day looks like, premium finishes throughout the building ensure it will be extraordinary. Unbeatable Foot Traffic. With a direct connection to the 606 Trail, and steps from public transportation, the retail spaces at Trailhead are unmatched. Choose from 7,265 SF divisible on Western Ave., 2,568 SF on The 606 Trail, including outdoor patio seating and signage directly on The Trail, or combine to offer a presence on both.
Application Fee: $75.00 per applicant/guarantor (non-refundable) Move-In/Administrative Fee: $500.00 (Due upon approval, non-refundable)   Bundled Services: (includes gas, water, sewer, trash and recycling) Studio - $115.00/Mo. One Bedroom - $140.00/Mo. Two Bedrooms - $165.00/Mo. Three Bedrooms - $190.00/Mo. Storage: $50.00/Mo Pet Policy & Fees. Monthly Pet Rent - $30.00/Mo. per pet + $100 one-time pet fee per pet. Maximum of 2 Pets per Unit Please contact the leasing office for breed restrictions Assigned Parking: $325.00/Mo per space Bike Storage: $15.00/Mo.
View more Request your own private tour

Ratings and Reviews

5.0 Exceptional
9 Reviews
  • Parking
    5/5
  • Amenities
    5/5
  • Maintenance
    5/5
  • Staff
    5/5
  • Value
    5/5
  • Location
    5/5
  • Noise
    5/5

Why Renters Love It Here

Renters appreciate the modern and clean design of the building, its friendly and polite community, and the fact that it is well-maintained and pet-friendly. The property has a welcoming atmosphere, often described as feeling like home, with spacious and open floor plans. Residents also value the efficient and friendly management and maintenance staff, who ensure the building remains in excellent condition. The inclusion of upcoming amenities such as a restaurant is a noted benefit. Overall, the property is praised for its high-end feel at affordable rates and its quiet units that offer a peaceful living experience.
AI-generated summary based on renter reviews.
Verified Resident

New and convenient

The trailhead building is one of the best buildings in the neighborhood! Conveniently located and amazing staff!

Anonymous Aug 4, 2025
Verified Resident

High End Living at a affordable rates

I've lived here for 4 years the management and staff are on top of EVERYTHING. The building is super clean and the staff is on top of every. The other tenants are quite and very polite,and clean

Nicholas C. May 2, 2025
Verified Resident

Feels like a community

This building makes you feel like you're living in a community everybody is very polite the building is very well kept very clean Pet friendly

Nicholas C. Oct 2, 2024
Verified Resident

High-end living, At affordable rates

I've lived at trailhead for 4 years now The look the design the residence the staff are unbelievable we are about to get a restaurant in a commercial floor of the building just another one of the features I chose to live here for. I recommend trail head for anyone that wants to be close to transportation close to nightlife live a high-end lifestyle at affordable rates. The maintenance and the staff are unbelievable Britney the on-site manager She is on top of the building she treats everybody as an equal It's good to have the Cagan management staff Managing this building

Nicholas C. Apr 12, 2024
Verified Resident

Feels like a home

I love the building it's modern its clean has friendly neighbors. Close to everything. It's just feels like I'm home. I see myself here for long term

Nicholas C. Mar 2, 2023
View more reviews

Average Utility Costs in Illinois

Electricity
$110
Gas
$111
Water
$29
Sewer
$29
Cable
$64
Internet
$35

Prices in the Area

This Community West Side Chicago Chicago, IL
Studio $2,430 $1,030 - $6,375 $300 - $20,000
1 Bed1 Bedroom $2,385 - $3,055 $225 - $7,750 $225 - $20,000
2 Beds2 Bedrooms $4,440 $1,195 - $9,365 $382 - $20,000
3 Beds3 Bedrooms $4,440 $1,000 - $8,099 $800 - $29,872

Location

1744 N Western Ave, Chicago, IL 60647
Points of interest powered by OpenStreetMap
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Calculate commute by driving, cycling or walking, where available.
Commute calculator powered by Walk Score® Travel Time
93 /100
Walker's Paradise
70 /100
Excellent Transit
98 /100
Biker's Paradise
Walk Score®: 93, Transit Score®: 70, Bike Score®: 98

  • Western & St. Paul 0.02 mi
  • Western & Bloomingdale 0.06 mi
  • Western 0.16 mi
  • Western & Cortland (Blue Line) 0.17 mi
  • Western Blue Line Station 0.17 mi
  • Milwaukee & Oakley/Moffat 0.18 mi
Nearby Transit
Points of interest powered by OpenStreetMap

  • Advanced Cleaners 0.06 mi
  • Sherwin-Williams 0.10 mi
  • Challengers Comics 0.13 mi
  • Kling Bros Insurance 0.18 mi
  • Odd Obsession 0.19 mi
  • Earth Rider Cycling 0.20 mi
Nearby Shops
  • Dunkin' 0.12 mi
  • Baskin-Robbins 0.12 mi
  • Dark Matter Coffee - Electric Mud Coffee Bar 0.15 mi
  • Tamazula Grocery 0.15 mi
  • Le Café Station Grill 0.17 mi
  • Sweet Rice Thai Street Food 0.17 mi
Nearby Food
  • Angelo Medical Clinic 0.20 mi
  • Walgreens 0.20 mi
  • Dental Magic 0.22 mi
  • Northwestern Immediate Care 0.24 mi
  • Walgreens 0.31 mi
  • Apple Dental Care 0.40 mi
Nearby Health
  • Black River Barbershop 0.14 mi
  • Karen Marie Salon 0.20 mi
  • Sugar Fly 0.23 mi
  • Check Express 0.23 mi
  • Pink Nail Spa 0.33 mi
  • Little Broken Things 0.34 mi
Nearby Errands
  • Delgado's 0.11 mi
  • Western Ave & Winnebago Ave 0.15 mi
  • Enterprise 0.19 mi
  • Shell 0.19 mi
  • Campbell Ave & North Ave 0.22 mi
  • Milwaukee Ave & Wabansia Ave 0.33 mi
Nearby Car Services
  • Bucktown Music 0.18 mi
  • Maplewood Park 0.22 mi
  • Maplewood Park Fieldhouse 0.24 mi
  • Lucy Flower Park 0.25 mi
  • Park No. 567 0.25 mi
  • Rock Solid 0.27 mi
Nearby Recreation
Points of interest powered by OpenStreetMap

  • Cortland Preschool 0.33 mi
  • Guidepost Montessori 0.59 mi
  • Bubbles Academy 0.95 mi
  • Luis Munoz Marin Primary Center 1.28 mi
  • Rainforest Pre-School & Infant Center 1.31 mi
  • Mary Crane Center West Lakeview 1.47 mi
Nearby Childcare
  • 6 Pulaski International School of Chicago 0.42 mi
  • 4 Moos Elementary School 0.45 mi
  • 6 Chase Elementary School 0.47 mi
  • 2 Sabin Elementary Magnet School 0.48 mi
  • 2 De Diego Elementary Community Academy 0.52 mi
  • 5 Yates Elementary School 0.62 mi
School data provided by GreatSchools
Nearby Schools
Points of interest powered by OpenStreetMap

Contact Information

Cagan Management Group Company (847) 324-8964

Prices and availability for this property were last updated Today.

The following floorplans are available: studio apartments from $2,430, 1-bedroom apartments from $2,385, 2-bedrooms apartments from $4,440 and 3-bedrooms apartments from $4,440.

The most popular nearby apartments are: 1744 N. Western Ave, The Elle Apartments, North Harbor Tower and 1524 W Fullerton Ave.

Currently, 1744 N. Western Ave has 7 available units.

1744 N. Western Ave is located in the West Side Chicago neighborhood.