Second City Roofing & Exterior
Second City Roofing & Exterior is a roofing provider in Chicago, IL serving Chicago and surrounding areas. A family-owned and operated business with over 45 years of experience, Second City Roofing & Exterior offers a wide range of roofing services for both residential and commercial properties. Contact Second City Roofing & Exterior for a free estimate.
About Second City Roofing & Exterior
A family-owned and operated business with over 45 years of experience, Second City Roofing & Exterior offers a wide range of roofing services for both residential and commercial properties. They are fully licensed, bonded, and insured, providing durable, high-quality roofs. Our roofing crews install and repair asphalt shingles, metal roofing, tile, flat roof systems, and commercial roofing. We handle storm damage assessment, insurance claim assistance, gutter installation, fascia and soffit repair, and attic ventilation. Every roof we install comes with a manufacturer warranty plus our own workmanship warranty. We provide free drone-assisted roof inspections so you can see the condition of your roof from the ground without anyone climbing up. Serving Chicago and the greater Chicagoland area. Licensed Illinois contractor. We understand the extreme temperature swings from subzero winters to hot summers that challenge every home system in the Midwest.
6 years in business
Services
Roof Inspection
FeaturedComprehensive roof inspection with photo documentation. Identifies leaks, damage, and remaining lifespan.
Starting at $500 / visit
Roof Repair
FeaturedPatch leaks, replace damaged shingles, fix flashing, and seal penetrations. Emergency repairs available.
Starting at $500 / per repair
Full Roof Replacement
Complete tear-off and replacement with new underlayment, shingles/tile, flashing, and ridge vents. Includes permits.
Starting at $6950 / per roof
Gutter Installation
Seamless aluminum gutter installation with downspouts and leaf guards. Custom color matching.
Starting at $1100 / per home
Storm Damage Assessment
Insurance-ready storm damage assessment with detailed report. Help with insurance claim filing.
Starting at $500 / visit
Location
Not specified
Chicago, IL 60601
Typical Roofing Costs in Chicago
$5,000–$15,000
Costs vary based on project scope, materials, and complexity. Get a free quote from Second City Roofing & Exterior to compare pricing in Chicago.
Hours of Operation
Services Offered
Roof Inspection
Comprehensive roof inspection with photo documentation. Identifies leaks, damage, and remaining lifespan.
$500
starting at
Roof Repair
Patch leaks, replace damaged shingles, fix flashing, and seal penetrations. Emergency repairs available.
$500
starting at
Full Roof Replacement
Complete tear-off and replacement with new underlayment, shingles/tile, flashing, and ridge vents. Includes permits.
$6,950
starting at
Gutter Installation
Seamless aluminum gutter installation with downspouts and leaf guards. Custom color matching.
$1,100
starting at
Storm Damage Assessment
Insurance-ready storm damage assessment with detailed report. Help with insurance claim filing.
$500
starting at
Reviews
4.7
10 reviews
10 reviews
Alan W.
Upgraded from shingles to standing seam metal roof. More expensive upfront but should last 50 years. Installation crew was skilled and careful. Premium roofing work. (Chicago)
Response from Second City Roofing & Exterior
Thank you for trusting us with your roof! We stand behind our work 100%.
Victor S.
Complete tear-off and new shingle roof installed in two days. Crew was professional, cleaned up everything, and the new roof looks fantastic. Best roofing service near me. (Chicago)
Response from Second City Roofing & Exterior
We really appreciate you taking the time to leave this review. Your satisfaction is our top priority!
Joanne V.
Upgraded to architectural shingles and the curb appeal improvement is dramatic. Neighbors keep asking who did our roof. Top quality roofing work. (Chicago)
Response from Second City Roofing & Exterior
Thank you for trusting us with your roof! We stand behind our work 100%.
Irma Q.
They re-roofed all four buildings in our apartment complex. Coordinated with tenants, minimal disruption, and completed on schedule. Reliable large-scale roofing. (Chicago)
Response from Second City Roofing & Exterior
We are so grateful for your trust in us. Reviews like this motivate our entire team to keep raising the bar.
Stacy N.
Left a voicemail and they called back within an hour. Thats already better than 3 other places I tried. Got the work scheduled for the same week. Efficient from start to finish.
5 people found this helpful
Response from Second City Roofing & Exterior
Glad we could help with your roofing project! We take pride in serving the Chicago community. Thank you for the recommendation.
River J.
Hired Second City Roofing & Exterior for roofing work in Chicago. Got three quotes and they had the best combination of price and expertise. Very happy with the results.
9 people found this helpful
Response from Second City Roofing & Exterior
Thank you for choosing us for your roofing needs in Chicago! We appreciate the kind words and look forward to helping you again.
Harold A.
Needed a roof that would pass HOA approval. They helped us pick the right color and material, submitted the paperwork, and handled everything. Hassle-free roofing near me. (Chicago)
Derek J.
Had a leak around the chimney flashing. They came out, identified the problem, and repaired it the same day. No more leaks even after heavy rain. Solid roofing repair nearby. (Chicago)
Harold A.
Needed a roof that would pass HOA approval. They helped us pick the right color and material, submitted the paperwork, and handled everything. Hassle-free roofing near me. (Chicago)
Response from Second City Roofing & Exterior
Thank you for trusting us with your roof! We stand behind our work 100%.
Penny Y.
Signed up for annual maintenance. They check for damage, clean debris, and address small issues before they become big ones. Smart preventive roofing care. (Chicago)
Service Area
Serves Chicago and surrounding areas
Frequently Asked Questions
Last updated April 2026