The Big Rentals Guide to Towing an Equipment Trailer in and around Chicago, IL

The most dangerous part of an equipment rental isn't the drive. It's the two minutes you spend driving the machine up the ramps. A skid steer or a mini excavator going onto a trailer deck at the wrong angle, on a slick ramp, with the weight in the wrong place, is how machines get rolled and people get hurt — and it happens in the yard, before you've gone anywhere.

Get the trailer wrong for the machine and the ramps are too steep to load it. Get the securement wrong and the machine shifts on the Kennedy. Get the weight wrong and you're over a licensing line you didn't know existed. This guide covers the equipment trailers that match real Chicago machines, the Illinois rules that apply the second you couple up, and the loading, securing and staging that make an equipment trailer rental in Chicago its own particular job.

Why Chicago Renters Choose Equipment Trailers

Chicago and its suburbs run on construction, excavation, landscaping and site work, and all of it depends on getting compact machines to the job and back. Skid steers, mini excavators, compact track loaders, scissor and boom lifts, small tractors and large mowers all move on equipment trailers, because an equipment trailer is built to let a machine drive on and ride secured. For a contractor renting a machine or moving their own between sites, the trailer is the piece that connects the yard to the job. Read more about how an equipment trailer and a flatbed compare.

A lot of these machines are themselves rentals, picked up for a weekend or a single job and returned, and the trailer is what makes that possible without paying a delivery fee. The machine dictates everything, too: a stand-on skid steer for a tight backyard and a mini excavator for a foundation or drainage job are different loads that need different trailers. Read more about what trailer you need to haul a mini excavator.

Much of this work is out in the collar counties and the suburbs, where sites have room and the drive back into the city is on the expressways. Wherever the job is, you'll find trailer rentals across the Chicago area from local owners near you.

Illinois Towing Laws Every Equipment Trailer Renter Should Know

A machine puts you in the top brake tier

Illinois tiers its brake rule (625 ILCS 5/12-301): no brakes under 3,000 lb, brakes on one wheel per side from 3,000 to 5,000 lb, and brakes on all wheels plus an automatic breakaway over 5,000 lb. For an equipment trailer that top tier is a given. A compact machine alone runs several thousand pounds, so the trailer plus the machine is over 5,000 lb the moment it's loaded, which means all-wheel brakes and a working breakaway every single time.

Confirm the trailer's brakes and breakaway work, and confirm your tow vehicle's brake controller, before you leave. Check the gross vehicle weight rating (GVWR) on the listing before you book. Read more about what GVWR means and how to read it.

Securing the machine, and the attachment

Under 625 ILCS 5/15-109, nothing may drop, shift or escape from the load. For a machine that means chains and rated binders at four points, to the machine's designated tie-down points, not straps thrown over it. Two things people miss: lower the boom or bucket to the deck and secure it, and secure or remove any loose attachment. An unsecured bucket or a swinging boom is its own hazard. Two safety chains are required, and the drawbar can't exceed 15 ft (625 ILCS 5/15-110). Read more about how to load and secure equipment on an equipment trailer.

The licensing line heavier trailers cross

For most equipment-trailer rentals — a 7,000 to 10,000 lb trailer with a compact machine behind a standard pickup — a regular Illinois Class D license is all you need. But Illinois requires a Class A once the trailer's GVWR is over 10,000 lb and the combination tops 26,001 lb. Equipment trailers are the class of trailer that actually reaches those ratings, so a heavy equipment trailer behind a big truck can put you over a line that a utility or small flatbed trailer never approaches.

The takeaway is simple: know the trailer's GVWR before you book, and know your combined rating. It's a real threshold, and it's easy to cross without realizing it.

Width, height and wide machines

Legal width is 8 ft 6 in, height is 13 ft 6 in, a trailer can run up to 42 ft and a combination up to 60 ft (625 ILCS 5/15-102, 103, 107). A machine wider than the deck is where an oversize permit can come into play, so measure the machine, not just the trailer.

Matching an Equipment Trailer to Your Machine

The machine dictates the trailer

Start from the machine's operating weight and its dimensions, not from the trailer. A stand-on skid steer, a full-size skid steer, a mini excavator and a scissor lift are all different loads, so match the trailer's weight rating to the machine's operating weight plus any attachment, with margin to spare. Read more about how to choose an equipment trailer by machine weight and width.

Deck height, dovetail and ramps

This is the equipment trailer's defining feature. A lower deck and a dovetail — the angled rear section — flatten the ramp angle so a low machine can climb on without high-centering. Steep ramps and a low machine are how loading goes wrong. Match the ramp type and angle to the machine, because a tracked mini excavator, a wheeled skid steer and a lift each load differently.

Loading discipline

Load on level ground, with a spotter watching, the machine centered on the deck, and drive slowly and straight up the ramps with the heaviest end uphill per the machine's own guidance. Never turn on the ramps. This is the two minutes the whole post is about, so do it calm, in the yard, and not in a hurry on a crowded job site. Read more about using ramps, winches and tie-downs to load an equipment trailer.

Hitch, brake controller and weight distribution

Match the coupler to the ball, confirm the receiver class and the brake controller, and place the machine for about 10% to 15% tongue weight. A machine too far back makes the trailer sway; too far forward overloads the hitch. Get it centered and forward, then chain it down.

Loading, Staging and Hauling a Machine in Chicago

Where do you load a machine in this city?

Chicago prohibits parking a trailer on any residential or business street, at any time, with an exception only for actively loading or unloading, and a trailer parked in violation can be impounded without prior notice (Chicago Municipal Code § 9-64-170). For an equipment trailer that's a real constraint, because loading or unloading a machine takes time and space — you can't stage the trailer at the curb and run the machine up whenever you're ready. Sort out a driveway, a yard, a lot or the job site itself for both the load and the unload before you book.

A tall machine and the viaducts

Illinois gives you 13 ft 6 in of legal height, but Chicago is full of viaducts and rail bridges posted lower. A mini excavator's cab, a scissor lift or a raised boom sitting up on a deck eats clearance fast, so measure the loaded height and plan the route around the low bridges. The underside of a viaduct is an expensive way to learn the clearance. Keep the loaded trailer on the truck routes and expressways, and off the boulevards and DuSable Lake Shore Drive (§ 9-72-020).

Winter on the ramps

Chicago winters turn the loading job dangerous. Ice on steel ramps and a snow-covered deck are exactly the conditions that send a machine sideways during a load. Clear the ramps and deck to bare metal, sand or salt the footing, and never load a machine on ice. If you can wait for a clear day to load, wait.

Stop-and-go and the tie-down check

The Kennedy and the Dan Ryan are stop-and-go for much of the day, and repeated hard braking works on a heavy machine's securement. Recheck the chains and binders after the first few miles and again at your first real stop.

Insurance and Damage Protection

What about insurance and damage protection?

Before towing a rented trailer, contact your auto insurance provider to ask whether your policy covers liability and towing-related damage claims.

Eligible rentals booked through Big Rentals also include Basic Rental Protection at checkout. This added protection can help limit your financial responsibility for certain damage or theft events during the rental period.

For full details on how Basic Rental Protection works, including deductibles, exclusions, and renter responsibilities, review our FAQ and platform terms.

Ready To Book?

Match the trailer to the machine, load calm on level ground, secure the machine and its attachment, and know your GVWR and your route before you pull out. Do that and an equipment trailer is the safest, most reliable way to get a compact machine from the yard to the job. When you're ready, browse equipment trailer rentals in Chicago from local owners near you.

The Short Version

• Equipment trailers move Chicago's compact machines — skid steers, mini excavators, compact track loaders, lifts and small tractors — between the yard and the job site.
• Loading the machine is the dangerous part. Load on level ground with a spotter, drive slowly and straight up the ramps, and never turn on the ramps.
• A loaded equipment trailer is always over Illinois's 5,000 lb brake tier, so all-wheel brakes and an automatic breakaway are a given (625 ILCS 5/12-301). Confirm the brake controller in your tow vehicle.
• Secure the machine with chains and binders at four points, lower and secure the boom or bucket, and secure any attachment separately (625 ILCS 5/15-109).
• Most rentals stay on a standard Class D license, but a trailer over 10,000 lb GVWR with a combination over 26,001 lb needs a Class A. Know the trailer's GVWR.
• Chicago bars parking a trailer on the street except while actively loading (§ 9-64-170), so plan where the machine gets loaded and unloaded. Measure a tall machine's height for the viaducts.