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New & Used Trailers for Sale in Chicago

Discover 43528 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 Diamond C 2026 Diamond C Tandem Utility Trailer  GTU235 14x83
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2026 Diamond C General Tandem Utility Trailer - GTU235 14x83 Carbon Metallic Gray - (2) 3500 lb Axles w/ 5...

Manufacturer
Diamond C Trailers
Condition
new
$8,599
Cumming, GA
2026 Top Hat Trailers Utility Trailer 77" X 14 Tube  Top Rear LAY-N-TAIL GATE Brakes
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Here you are looking at a NEW Top Hat Utility Trailer Tube - Top 77 X 14 with Heavy Duty...

Manufacturer
Top Hat Trailers
Condition
new
$3,450
Kansas City, MO
2026 Sport Haven AUT610D Utility Trailer
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NEW 2026 SPORT HAVEN AUT510D DELUXE / 6' x 10' / ALL ALUMINUM UTILITY TRAILER-2990 GVWR / CARRY CAPACITY 2470LBS...

Manufacturer
Sport Haven
Condition
new
$4,482
Antioch, IL
2026 Arising Enclosed Trailer 4 X 8 Ramp Door 5' Interior Black In Color
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New Arising Soft Nose 4 X 8 Enclosed - 5' Interior height - Black In Color - Ramp Door -...

Manufacturer
Arising
Condition
new
$3,745
Kansas City, MO
2026 Homesteader Trailers 612IS Enclosed Trailer
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2026 HOMESTEADER 612 INTREPID SERIES 6x12, V-Nose Enclosed Trailer with Ramp, White - The Intrepid is an exciting series packed...

Manufacturer
Homesteader Trailers
Condition
new
$5,295
Port Monmouth, NJ
 Lamar 83X14 Telescopic Dump Trailer - 14Ply Tires - Sola
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What Lamar dump trailers have that other dump trailers don't: 6" Cylinder -- not a 5" -- 6" Cylinder Provides...

Manufacturer
Lamar Trailers
Condition
new
Length
14' 0
$13,499
Lubbock, TX
2018 Liberty Trailers 5'x8' SA Utility
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USED 2018 Liberty 5' x8' SA Utility 1-3,500 lbs Spring Axle 15" Radial Tires Drop Leg Jack 12" Rail Sides...

Manufacturer
Liberty
Condition
used
Length
8' 0
$1,800
Middlebury, IN
2026 Homesteader Trailers Hercules Series 714HT (7 x 14)
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$14,799
New Tazewell, TN
2025 Trailer Source Manufacturing LLC 7x16 Enclosed Black Trailer ? 7K GVWR, Brakes, Bar Locks, B
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This 7x16 enclosed trailer features a sleek black-on-black design with a 7,000 lb GVWR, making it ideal for secure and...

Manufacturer
Other
Condition
used
$5,908
Mima, FL
2020 Big Tex Trailers 35SA 12'
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KNAPHEIDE is pleased to offer for sale this USED 2020 Big Tex Single Axle Utility Trailer with the following specs:...

Manufacturer
Big Tex Trailers
Condition
used
Pull Type
bumper
Length
12' 0
$1,975
Mchenry, IL
TRIPLE AXEL BOAT TRAILER
Rocket Trailers

TRIPLE AXEL BOAT TRAILER in Port Charlotte, FL

Like new Triple Axel Aluminum Boat Trailer for sale: \*Purchased May, 2025 \*Never immersed in water Pulled it home from...

$11,250
Port Charlotte, FL
2026 Arising Enclosed Trailer 4 X 8 Ramp Door 5' Interior Silver Mist In Color 030 Skin
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New Arising Soft Nose 4 X 8 Enclosed "Soft Nose Trailer" - 5' Interior height - Silver In Color -...

Manufacturer
Arising
Condition
new
$4,145
Kansas City, MO
2026 Cargo Craft EV-Elite V-Nose 8.5' x 16' Tandem Axle Cargo / Enclosed Trailer Polycor Siding (
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2026 CARGO CRAFT ELITE 8.5x16 V-NOSE ENCLOSED TRAILER 8.5 x 16 Tandem axle Polycor exterior (White) V-nose front Rear spoiler...

Manufacturer
Cargo Craft
Condition
new
$6,999
Waxahachie, TX
2024 H&H 82"X20' 17.6k Topline I-Beam Equipment Trailer
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H&H Trailers 82" x20' - 17.6k Topline I-Beam Equipment Trailer - 2-8,000lbs Slipper Spring Axles, 17,600lbs GVWR 17.5" Radial Tires...

Manufacturer
Other
Condition
used
Length
1' 8
$10,800
Middlebury, IN
2025 Anvil -New 8x12 BlackOut - .080 Polycore Ext - Electric Pkg with A/C - Enclosed Trailer
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$0 Dealer, Doc, Or Prep Fees - $0 Or 10% Down Special Financing Available - Now In Stock @ Ohio...

Manufacturer
Anvil Trailers
Condition
new
$10,190
Lebanon, OH

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