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New & Used Trailers for Sale in Chicago

Discover 42026 trailers of popular models like Cargo (Enclosed) Trailers, Utility Trailers and more in Chicago from leading manufacturers like Load Trail, Sure-trac, Big Tex Trailers and more. Start browsing now and connect with trusted dealers and private sellers.

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2026 Legend Trailers 7.5X18TVTA35-7.5x16 Thunder
Enhanced

Legend 7.5X18TVTA35-7.5x16 Thunder Enclosed Cargo Upgrades Included: 6"" Extra Height (7' Interior Height) 24"" Beavertail Deluxe Road Side Gull Wing...

Manufacturer
Legend Trailers
Condition
new
Pull Type
bumper
Weight
1969 lbs
Length
16' 0
$13,495
Fenton, MI
2026 Legend Trailers 7X14TVSA30 3K Cargo / Enclosed Trailer
Enhanced
Manufacturer
Legend Trailers
Condition
new
Weight
1260 lbs
Length
14' 0
SALE
$6,858$8,070
Hinckley, MN
2026 Sure-Trac 6 x 10 Tube Top Three Board 3K Idler
Enhanced

Standard Features 3" x 2" x 3/16" Steel Angle 3" x 2" x 3/16" Steel Angle 3" Steel Channel 2"...

Manufacturer
Sure-Trac
Condition
new
Pull Type
bumper
Weight
1230 lbs
Length
10' 0
CONTACT SELLER FOR PRICE
Markle, IN
2026 Diamond Cargo 8.5X28 Custom Race 6K Cargo / Enclosed Trailer
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CONTACT SELLER FOR PRICE
Cochran, GA
2027 4-Star Trailers 2027 test General Trailers
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High Country All Aluminum8.5-Wide Cargo Trailers are built for large cargo hauling needs. Features include: * All Aluminum Box Tube...

Manufacturer
4-Star Trailers
Condition
new
Length
4' 3
$99,999
Tuppers Plains, OH
2026 Sure-Trac 7 x 14 Tube Top Three Board 7K
Enhanced

Standard Features Full LED, DOT Compliant Spare Tire Carrier (4) 1/2" D-Rings Board Retainers 2" Pressure Treated Pine Industrial Grade...

Manufacturer
Sure-Trac
Condition
new
Pull Type
bumper
Weight
2040 lbs
Length
14' 0
CONTACT SELLER FOR PRICE
Markle, IN
83" X 14' TANDEM AXLE DUMP (8" X 13LB. I-BEAM)
Enhanced

2 - 7,000 Lb Dexter Spring Axles (2 Elec FSA Brakes) ST235/80 R16 LRE 10 Ply. (BLACK WHEELS) Coupler 2-5/16"...

Manufacturer
Load Trail
Condition
new
CONTACT SELLER FOR PRICE
Poplar Bluff, MO
2026 Legend Trailers 7.5X18CESTA35 Cargo / Enclosed Trailer
Enhanced
Manufacturer
Legend Trailers
Condition
new
Weight
2510 lbs
Length
18' 0
SALE
$8,419$9,906
Hinckley, MN
2014 Idaho Tote/Freedom Hauler
Other

2014 Idaho Tote/Freedom Hauler in Meridian, ID

2014 Idaho Tote/Freedom Hauler trailer. The bed is 8'-6" wide x 8' long. I purchased this trailer new in 2014....

$5,500
Meridian, ID
2026 Diamond C Trailers HXD210 22ft 23K 102" Gravity Tilt Equipment Equipment Trailer
Enhanced

Diamond C HXD210 22ft 23K 102" Gravity Tilt Equipment ONYX BLACK MAX WIDE PACKAGE 102" Wide 10GA Drive Over Fenders...

Manufacturer
Diamond C Trailers
Condition
new
$17,900
Leeds, AL
2026 Legend Trailers 7X14CESSA30 3K Cargo / Enclosed Trailer
Enhanced
Manufacturer
Legend Trailers
Condition
new
Weight
1507 lbs
Length
14' 0
SALE
$5,701$6,708
Hinckley, MN
2026 Sure-Trac 6 x 12 Tube Top Three Board 3K
Enhanced

OVERVIEW The Three Board High Side Utility Trailer is a versatile and practical solution designed to meet a wide array...

Manufacturer
Sure-Trac
Condition
new
Pull Type
bumper
Weight
1300 lbs
Length
12' 0
CONTACT SELLER FOR PRICE
Markle, IN
2026 Diamond C Trailers HXD210 22ft 23K 102" Gravity Tilt Equipment Equipment Trailer
Enhanced

Diamond C HXD210 22ft 23K 102" Gravity Tilt Equipment CEMENT GRAY MAX WIDE PACKAGE 102" Wide 10GA Drive Over Fenders...

Manufacturer
Diamond C Trailers
Condition
new
$18,900
Leeds, AL
83" X 16' TANDEM AXLE UTILITY (2" X 3" ANGLE FRAME)
Enhanced

2" x 3" Angle Frame 2 - 3,500 Lb Dexter Spring Axles (2 Elec FSA Brakes) ST205/75 R15 LRC 6...

Manufacturer
Load Trail
Condition
new
CONTACT SELLER FOR PRICE
Wausau, WI
2025 Criterion 8X14 / 8.5X14 .080 Aluminum Exterior Enclosed Carg
Enhanced
$10,980
Draper, UT

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