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Skid Steers for Sale near Chicago, IL

703 skid steers for sale within 400 miles of Chicago, IL, 22 of them within 100 miles. Prices run from $1,500 to $145,000. Sellers closest to Chicago include Altorfer Industries and Bedrock Machinery in Joliet and Proxy Equipment in Chicago.
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Showing 1 - 25 of 707 Skid Steer Listings

1 - 25 of 707 listings
1 - 25 of 707 listings
Featured Item
Caterpillar 289D3 Track Skid Steer

2023 Caterpillar 289D3 Track Skid Steer

Recently Updated
$69,500 USD
2 Speed Travel, Air Conditioner, Auxiliary Hydraulics Pressure - Standard Flow, Bucket, Coupler Type - Hydraulic, Heater / Defroster, Lighting, Online Owner's Manual, Pilot Control, Product...
ConditionUsed
Usage1,110 Hours
DrivetrainTrack
Stock Number266RU432
MLS Number14462478
CategorySkid Steers
Last Updated11/5/2026
Location
Joliet, IL, US
5 mi. from Chicago
Sold By
Altorfer Industries
(855) 929-___  SHOW
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Altorfer Industries
Featured Item
Caterpillar 262D3 Track Skid Steer

2023 Caterpillar 262D3 Track Skid Steer

Recently Updated
$60,500 USD
2 Speed Travel, Air Conditioner, Auxiliary Hydraulics Flow - Standard Flow, Bucket, Coupler Type - Hydraulic, Heater / Defroster, Lighting, Online Owner's Manual, Pilot Control, Product...
ConditionUsed
Usage319 Hours
Drivetrain4WD
Stock NumberUN01095
MLS Number14425764
CategorySkid Steers
Last Updated11/4/2026
Location
Joliet, IL, US
5 mi. from Chicago
Sold By
Altorfer Industries
(855) 929-___  SHOW
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Altorfer Industries
Featured Item
Caterpillar 226D3 C1H1 Track Skid Steer

2023 Caterpillar 226D3 C1H1 Track Skid Steer

Recently Updated
$15,000 USD
*DISPLAY, BASIC, ANTI-THEFT, *FAN, COOLING, DEMAND, *HYDRAULICS, PERFORMANCE (H1), *LIGHTS, LED, *QUICK COUPLER, MANUAL, *ROPS, OPEN (C1), *SEAT, SUSPENSION, VINYL, BATTERY,HD,DISCONNECT,...
Inspection Report
ConditionUsed
Usage5,118 Hours
Stock NumberEK501722
MLS Number14611941
CategorySkid Steers
Last Updated11/4/2026
Location
De Pere, WI, US
180 mi. from Chicago
Sold By
Fabick Cat
(855) 591-___  SHOW
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Fabick Cat
Featured Item
Caterpillar 239D3 Skid Steer

2022 Caterpillar 239D3 Skid Steer

$39,800 USD
2 Speed Travel, Air Conditioner, Auxiliary Hydraulics Flow - Standard Flow, Bucket, Coupler Type - Hydraulic, Heater / Defroster, Lighting, Online Owner's Manual, Radio - Bluetooth, ROPS -...
ConditionUsed
Usage1,112 Hours
DrivetrainTrack
Stock NumberEQ0098838
MLS Number13286700
CategorySkid Steers
Last Updated10/6/2026
Location
Hugo, MN, US
355 mi. from Chicago
Sold By
Ziegler CAT
(855) 952-___  SHOW
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Ziegler CAT
Case 85XT Skid Steer

1999 Case 85XT Skid Steer

$18,500 USD
1999 Case 85TX Turbo Skid Steer, 4993 hours, 80 HP, 8057 Lbs. Operating Weight, 2400 Lbs. Lift Capacity, 1680 Lbs. Operating Capacity, 72" bucket width This 1999 Case 85XT turbo skid steer...
ConditionUsed
Usage4,993 Hours
Stock NumberPEI0APGa412945
MLS Number12954863
CategorySkid Steers
Last Updated8/25/2026
Location
Chicago, IL, US
11 mi. from Chicago
Sold By
Proxy Equipment
(844) 734-___  SHOW
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Proxy Equipment
Caterpillar MINI EXCAVATOR/SKID STEER LOADER 6 WAY BLADE Track Skid Steer

2026 Caterpillar MINI EXCAVATOR/SKID STEER LOADER 6 WAY BLADE Track Skid Steer

Contact for price
Mini Hydraulic Excavator/Skid Steer Loader 6 Way Blade, 92in, SKU: SK6W-92 Part Number: 5410945B, The heavy-duty VPAT blade is engineered to provide simultaneous tilting and angling...
ConditionNew
Stock NumberSK6W-92
MLS Number13865815
CategorySkid Steers
Last Updated1/24/2026
Location
Joliet, IL, US
34 mi. from Chicago
Sold By
Bedrock Machinery
(855) 999-___  SHOW
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Bedrock Machinery
Caterpillar 299D3 XE Track Skid Steer

2020 Caterpillar 299D3 XE Track Skid Steer

Recently Updated
$55,000 USD
**CCU ELIGLBLE MACHINE WITH, *FAN,COOLING, DEMAND, REVERSING, *LIGHTS, LED, *RADIO, AM/FM, BLUETOOTH, *RUBBER BELT, 2 SPD, TF IDLERS, CAB PACKAGE, ULTRA, CERTIFICATION ARR, P65, DEBRIS MGMT...
Inspection Report
ConditionUsed
Usage2,021 Hours
DrivetrainTrack
Stock NumberBX901756
MLS Number14579477
CategorySkid Steers
Last Updated11/4/2026
Location
Sturtevant, WI, US
61 mi. from Chicago
Sold By
Fabick Cat
(855) 591-___  SHOW
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Fabick Cat
Caterpillar 299D3 Track Skid Steer

2020 Caterpillar 299D3 Track Skid Steer

Recently Updated
$48,000 USD
****ATTACHMENTS PICTURED ARE****, ***BE INCLUDED IN THE PRICING***, **SUBJECT TO CHANGE AND MAY NOT*, *299D3 COMPACT TRACK LOADER, *BATTERY,EXTRA HD,DISC,1000 CCA, *CAB PACKAGE, PRO PLUS,...
Inspection Report
ConditionUsed
Usage2,152 Hours
DrivetrainTrack
Stock NumberDY903167
MLS Number14568082
CategorySkid Steers
Last Updated11/4/2026
Location
Sturtevant, WI, US
61 mi. from Chicago
Sold By
Fabick Cat
(855) 591-___  SHOW
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Fabick Cat
Kubota SL95-2S Skid Steer

2019 Kubota SL95-2S Skid Steer

Newly Listed
$46,000 USD
2 Speed Travel, Air Conditioner, Auxiliary Hydraulics Flow - High Flow, Bucket, Coupler Type - Hydraulic, Forks - Pallet, Heater / Defroster, Lighting, Pilot Control, Radio - Bluetooth, ROPS...
Inspection Report
ConditionUsed
Usage773 Hours
MLS Number14715000
CategorySkid Steers
Last Updated11/4/2026
Location
Niles, MI, US
74 mi. from Chicago
Sold By
MacAllister Machinery
(833) 980-___  SHOW
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MacAllister Machinery
Caterpillar 279D3 Tracked Skid Steer

2022 Caterpillar 279D3 Tracked Skid Steer

Newly Listed
$47,000 USD
2 Speed Travel, Air Conditioner, Auxiliary Hydraulics Flow - Standard Flow, Bucket, Coupler Type - Hydraulic, Online Owner's Manual, ROPS - Enclosed,
ConditionUsed
Usage1,925 Hours
DrivetrainTrack
Stock NumberRB904245
MLS Number14714966
CategorySkid Steers
Last Updated11/4/2026
Location
Niles, MI, US
74 mi. from Chicago
Sold By
MacAllister Machinery
(833) 980-___  SHOW
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MacAllister Machinery
New Holland L316 Skid Steer

2022 New Holland L316 Skid Steer

$25,900 USD
2022 New Holland L316 Skid Steer, Cab w/HVAC, Air Ride Suspension Seat, HYD Quick-tach, Foot Controls, Block Heater, AC, Heater, Enclosed ROPS, Cloth Air-Ride Seat, Quick Attach,
ConditionUsed
Usage2,287 Hours
Horse Power60 HP
Engine ModelN844LT
Drivetrain4WD
Capacity1600
Enclosed CabYes
Stock Number22RE005
MLS Number13294850
CategorySkid Steers
Last Updated10/8/2025
Location
Winimac, IN, US
78 mi. from Chicago
Sold By
Vander Haag's Inc.
(855) 370-___  SHOW
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Vander Haag's Inc.
Caterpillar 259D3 Tracked Skid Steer

2021 Caterpillar 259D3 Tracked Skid Steer

Newly Listed
$49,000 USD
2 Speed Travel, Air Conditioner, Auxiliary Hydraulics Flow - Standard Flow, Bucket, Coupler Type - Hydraulic, Heater / Defroster, Lighting, Online Owner's Manual, Product Link, ROPS -...
ConditionUsed
Usage1,229 Hours
DrivetrainTrack
Stock NumberUS01851
MLS Number14706906
CategorySkid Steers
Last Updated10/30/2026
Location
Springfield, IL, US
81 mi. from Chicago
Sold By
Altorfer Industries
(855) 929-___  SHOW
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Altorfer Industries
New Holland L220 Skid Steer

2011 New Holland L220 Skid Steer

$38,500 USD
2011 New Holland L220 Skid Steer Superboom, 1,804 hrs. Aux hydraulics (High-Flow), Air heat in enclosed cab, Foot controls, 72" Bucket, 67 HP diesel, Operating Weight 6,459 lbs. Ground...
ConditionUsed
Usage1,804 Hours
Stock NumberTOT0fLoA919390
MLS Number12983728
CategorySkid Steers
Last Updated9/29/2026
Location
Milwaukee, WI, US
84 mi. from Chicago
Sold By
Proxy Equipment
(844) 734-___  SHOW
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Proxy Equipment
Caterpillar 232D3 C3H2 Mini Skid Steer

2024 Caterpillar 232D3 C3H2 Mini Skid Steer

Recently Updated
$30,000 USD
**ATTACHMENTS PICTURED ARE, 232D3 M205 CPM, AXLES, STANDARD, BATTERY,HD,DISCONNECT, 850 CCA, BE INCLUDED IN THE PRICING**, CAB PACKAGE, PRO PLUS, CERTIFICATION ARR, P65, DOOR, CAB, GLASS,...
Inspection Report
ConditionUsed
Usage2,878 Hours
Stock NumberGJ501254
MLS Number14568093
CategorySkid Steers
Last Updated11/4/2026
Location
Milwaukee, WI, US
90 mi. from Chicago
Sold By
Fabick Cat
(855) 591-___  SHOW
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Fabick Cat
Caterpillar 299D2 Track Skid Steer Loader

2019 Caterpillar 299D2 Track Skid Steer Loader

Recently Updated
$46,000 USD
****ATTACHMENTS PICTURED ARE****, ***BE INCLUDED IN THE PRICING***, **SUBJECT TO CHANGE AND MAY NOT*, 299D2 COMPACT TRACK LOADER, 299D2 CTL DCA2, BATTERY, HEAVY DUTY, DISC, BUCKET-GP, 86 IN....
Inspection Report
ConditionUsed
Usage1,876 Hours
DrivetrainTrack
Stock NumberFD204783
MLS Number14556676
CategorySkid Steers
Last Updated11/4/2026
Location
Milwaukee, WI, US
90 mi. from Chicago
Sold By
Fabick Cat
(855) 591-___  SHOW
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Fabick Cat
Caterpillar 259D3 Tracked Skid Steer

2022 Caterpillar 259D3 Tracked Skid Steer

Recently Updated
$40,000 USD
**CCU ELIGLBLE MACHINE WITH, *DISPLAY, ADVANCED, LCD, CAMERA, *FAN, COOLING, DEMAND, *FILM, TWO SPEED, *HYDRAULICS, PERFORMANCE, (H2), *LIGHTS, LED, *QUICK COUPLER, HYDRAULIC, *ROPS,...
Inspection Report
ConditionUsed
Usage2,794 Hours
DrivetrainTrack
Stock NumberCW919729
MLS Number14568067
CategorySkid Steers
Last Updated11/4/2026
Location
Milwaukee, WI, US
90 mi. from Chicago
Sold By
Fabick Cat
(855) 591-___  SHOW
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Fabick Cat
Caterpillar 259D3 Tracked Skid Steer

2022 Caterpillar 259D3 Tracked Skid Steer

Recently Updated
$40,000 USD
**CCU ELIGLBLE MACHINE WITH, *DISPLAY, ADVANCED, LCD, CAMERA, *FAN, COOLING, DEMAND, *FILM, TWO SPEED, *HYDRAULICS, PERFORMANCE, (H2), *LIGHTS, LED, *QUICK COUPLER, HYDRAULIC, *ROPS,...
Inspection Report
ConditionUsed
Usage2,665 Hours
DrivetrainTrack
Stock NumberCW919727
MLS Number14568065
CategorySkid Steers
Last Updated11/4/2026
Location
Milwaukee, WI, US
90 mi. from Chicago
Sold By
Fabick Cat
(855) 591-___  SHOW
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Fabick Cat
Caterpillar 262D3 Track Skid Steer

2024 Caterpillar 262D3 Track Skid Steer

Recently Updated
$39,000 USD
*262D3 SKID STEER LOADER, *BATTERY,EXTRA HEAVY DUTY, DISC, *CERTIFICATION ARR, P65, *CONTROL, ISO, PROP, WT, *DISPLAY, ADVANCED, LCD, CAMERA, *DOOR, CAB, GLASS, *FAN, COOLING, DEMAND, *FILM,...
Inspection Report
ConditionUsed
Usage2,966 Hours
Drivetrain4WD
Stock NumberTP401853
MLS Number14567852
CategorySkid Steers
Last Updated11/4/2026
Location
Milwaukee, WI, US
90 mi. from Chicago
Sold By
Fabick Cat
(855) 591-___  SHOW
NUMBERCall Seller
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Fabick Cat
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