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Three technicians in blue uniforms installing an outdoor air conditioning unit near a building wall.

1. HVAC contractors

As temperatures drop, your heating system needs to be ready for a Chicago winter. Fall is the ideal time to tune up your furnace, repair issues, or replace an aging system before the cold sets in.

Two workers in protective gear repairing a house roof, one on a ladder and the other walking on the shingles.

2. Roofing contractors

Winter can be rough on your roof. Fall is the ideal time to inspect for damage, replace shingles, and fix leaks before spring storms roll in.

Worker on ladder power washing a roof gutter on a sunny day, with flowers visible below.

3. Gutter cleaning and repair

Fall leaves can quickly clog your gutters and downspouts. Cleaning and repairing them now helps prevent water damage, ice dams, and drainage problems before Chicago’s winter weather arrives.

A man inspecting plumbing under a kitchen sink, holding a clipboard. A toolbox with tools is nearby.

4. Plumbing

Cold Chicago winters can put extra stress on your plumbing. Fall is a good time to fix leaks, address sewer or drain issues, and prepare pipes and water systems before freezing temperatures arrive.

Technician in a hard hat installing wires in a brick wall at a construction site.

5. Water heater repair

Cold weather means your water heater will be working harder. Fall is a great time to repair, maintain, or replace an aging water heater before winter demand puts it to the test.

Two professionals in a partially renovated room, one holding blueprints and the other wearing a hard hat and safety vest.

6. Insulation contractors

A well-insulated home stays warmer and more comfortable through a Chicago winter. Fall is the ideal time to seal drafts, improve insulation, and prepare your home for colder temperatures and higher heating costs.

Gardener in uniform trimming a bush with shears in a well-maintained garden, wearing gloves and a green cap.

7. Tree services

Fall is a good time to trim weak or damaged branches and remove hazardous trees before winter storms arrive. Taking care of tree work now can help protect your home and property from wind, ice, and snow damage.

Technician in a hard hat installing wires in a brick wall at a construction site.

8. Chimney and fireplace

Before you light the fireplace this winter, make sure your chimney and fireplace are ready. Fall is the ideal time for inspections, cleanings, and repairs to help keep your home warm and safe through the colder months.

Worker in a plaid shirt and hard hat installing a window frame in a building under construction.

9. Window and door services

Drafty windows and doors can make a Chicago winter feel even colder. Fall is the ideal time to repair, replace, or weatherproof them before freezing temperatures arrive and heating costs rise.

A worker uses a spirit level on a wall in a room under renovation, surrounded by tools, a ladder, and a toolbox.

10. Basement and waterproofing

Fall rain can reveal leaks and drainage problems before winter makes them worse. Now is a good time to repair foundation cracks, improve drainage, and address basement or sump pump issues before freezing temperatures arrive.