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New & Used Trailers for Sale in Chicago

Discover 68830 trailers of popular models like Cargo (Enclosed) Trailers, Utility Trailers and more in Chicago from leading manufacturers like Big Tex Trailers, Sure-trac, Load Trail and more. Start browsing now and connect with trusted dealers and private sellers.

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2026 Lamar 7x14' Dump Trailer 16000# GVW * 8000# AXLE UPGRADE * OVERSIZE 6X21.5 11-TON SCISSOR HOIST * 12K JACK * 7GA FLOOR * 17.5" 16-PLY TIRES * TARP KIT * CHARCOAL * RIGID RAILS * NESTLED I-BEAM FRAME

Unit has 8000# axle upgrade, tarp, ramps, 17.5" rubber, spare mount, spare tire, oil bath, rear support stands, and dual...

Manufacturer
Lamar Trailers
Condition
new
Pull Type
bumper
Payload Capacity
12780
Weight
4720 lbs
Length
14' 0
$13,495
Carlisle, PA
2026 Lamar 77x12' Utility Landscape Trailer 5200# GVW * 5200# AXLE * ELECTRIC BRAKES * CHANNEL FRAME * SPARE TIRE MOUNT * CAST COUPLER * SWIVEL JACK * COLD WEATHER HARNESS * STAKE POCKETS * LAY FLAT/TUBE GATE W/SPRING ASSIST * LED LIGHTS

THIS UNIT IS EQUIPPED WITH A 5200# BRAKE AXLE. IDEAL FOR A SMALL COMPACT TRACTOR, LARGER UTV, ETC. These utility...

Manufacturer
Lamar Trailers
Condition
new
Pull Type
bumper
Payload Capacity
3750
Weight
1450 lbs
Length
12' 0
$3,995
Carlisle, PA
2026 Summit 6' x 12' Cascade High Side Dump 10K Dump Trailer

Cascade Dump by Summit Trailer 6' x 12' x 40" - 9,990# GVWR Adjustable 2 5/16" Coupler Safety Chains 7K...

Feature 1
Slide In Ramps
SALE
$10,695$11,735
Tacoma, WA
2026 Lamar 7x16' Utility Landscape Trailer 9990# GVW * 5' HD RAMP W/ SPRING ASST * 16" 10-PLY TIRES * 12K JACK * 2' DOVETAIL * PIPE TOP * CHARCOAL * 12K JACK * 5" CHANNEL TONGUE/FRAME * CHANNEL C/M * ADJUSTABLE COUPLER

Landscaper's Delight! Here's an ideal mowing trailer with the HD channel frame and crossmembers (not angle iron like most utilities),...

Manufacturer
Lamar Trailers
Condition
new
Pull Type
bumper
Payload Capacity
7400
Weight
2590 lbs
Length
16' 0
$6,195
Carlisle, PA
2026 MAXX-D 102x22 Tandem 17.5K Power Tilt w/ Hydraulic Jack, Drive Over Fenders, & Spare Tire

22' X 102" - 14K HD Channel Power Tilt 17,500 LB GVWR 2 5/16" ADJUSTABLE COUPLER 1-HYDRAULIC JACK 8" CHANNEL...

Manufacturer
MAXX-D
Condition
new
Pull Type
bumper
Length
22' 0
$14,995
Diamond, MO
2026 Mission 6x12 Aluminum Utility w/Rear Ramp Gate, 20" Sides, HD D-Rings

2026 Mission 6x12 Aluminum Utility w/Rear Ramp Gate, 20" Sides, HD D-Rings. 435 lbs. 7.99% financing available Charcoal Options Added...

Manufacturer
Mission
Condition
new
Pull Type
bumper
Payload Capacity
1765
Weight
435 lbs
Length
12' 0
$3,750
Est. $68/Mo*
Manchester, ME
2021 Canada Trailers CE720-14K Equipment Trailer

STANDARD FEATURES SIZE: \\ \| 80" X 20'\| WEIGHT: 3,005 lbs PAYLOAD: 10,995 lbs \\ GVWR: 14,000 lbs AXLES: (2)...

Manufacturer
Canada Trailers
Condition
new
Pull Type
bumper
Payload Capacity
10995
SALE
CAD$8,995CAD$9,941
Nisku, AB
2025 HandiTrailers 14' Deckover Base Package Trailer \ 14K GVWR, Near Charlotte

Farms, construction companies, and landscapers, equipment suppliers, and others choose our 14-foot Deckover Base Trailer package as a dependable workhorse...

Manufacturer
HandiTrailers
Condition
new
Pull Type
bumper
Payload Capacity
10600
Weight
3400 lbs
Length
14' 0
$6,850
Denton, NC
2026 Lamar 102x28' Gooseneck Equipment Trailer 14000# GVW * WINCH PLATE IN NECK * 102" DECK * DRIVE OVER FENDERS * FULL WIDTH RAMPS * RUBRAIL * UNDER FRAME BRIDGE * DUAL JACKS * FULL TOOLBOX * CHARCOAL W/ BLACK WHEELS

EQUIPPED WITH OPTIONAL WINCH PLATE IN NECK, +4" GOOSENECK NECK HEIGHT, 102" DECK UPGRADE, DRIVER OVER FENDERS, FULL WIDTH RAMPS,...

Manufacturer
Lamar Trailers
Condition
new
Pull Type
gooseneck
Payload Capacity
10540
Weight
4960 lbs
Length
28' 0
$11,395
Carlisle, PA
2026 Load Trail 77x12 3K Utility w/ 4' Ramp Gate

77" x 12' Single Axle (2" x 3" Angle Frame) 1 - 3,500 Lb Dexter Spring (1 Idler Axle) ST205/75...

Manufacturer
Load Trail
Condition
new
Pull Type
bumper
Payload Capacity
1882
Weight
1108 lbs
Length
12' 0
$2,400
Diamond, MO
2026 NEO Trailers NAC126-6 Cargo / Enclosed Trailer

Neo All Aluminum Cargo Trailer. Where High Quality Meets Budget Friendly. The NAC Model is a Price Point Aluminum Trailer....

Manufacturer
NEO Trailers
Condition
new
Pull Type
bumper
Payload Capacity
5620
Weight
1380 lbs
Length
12' 0
$7,095
Grandville, MI
2026 Load Trail 83x20 Tandem 14K Equipment Trailer w/ Max Ramps & Tool Tray

83" x 20' Tandem Axle Carhauler * 6" Frame For MAX Ramps Dove (ONLY) * 2 - 7,000 Lb Dexter...

Manufacturer
Load Trail
Condition
new
Pull Type
bumper
Length
20' 0
$6,200
Diamond, MO
2026 Summit 6' x 12' Cascade High Side Dump 10K Dump Trailer

Cascade Dump by Summit Trailer 6' x 12' x 40" - 9,990# GVWR Adjustable 2 5/16" Coupler Safety Chains 7K...

Feature 1
Slide In Ramps
SALE
$10,695$11,735
Tacoma, WA
2026 Seed Cargo 7x16 35K Cargo / Enclosed Trailer
CONTACT SELLER FOR PRICE
Cochran, GA
2026 Load Trail 83x14 Tandem 14K Dump w/ 18" Sides

83" x 14' Tandem Axle Dump (8" x 13Lb. I-Beam) * 2 - 7,000 Lb Dexter Spring Axles (2 Elec...

Manufacturer
Load Trail
Condition
new
Pull Type
bumper
Payload Capacity
9814
Weight
4186 lbs
Length
14' 0
$8,600
Diamond, MO

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