Used 2027 Jeep Gladiator for Sale nearChicago, IL
221 vehicles found
Shop with transparent pricing.
Only show listings that include dealer fees- Year:
- 2026
- Make:
- Jeep
- Model:
- Gladiator
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 285 hp 3.6L V6
- Exterior color:
- 41
- Fuel type:
- Gasoline
- Interior color:
- Brown (Heritage Tan/Black)
- Transmission:
- 8-Speed Automatic
- Mileage:
- 79
- Stock #:
- D260948A
- VIN:
- 1C6PJTAG3TL175460
Sponsored by Hawk Chrysler Jeep Dodge RAM
2026 Jeep Gladiator
Willys '41 4dr Crew Cab 4WD
79 mi
Forest Park, IL
10 mi away
Fair Deal
$49,655
- Year:
- 2026
- Make:
- Jeep
- Model:
- Gladiator
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 285 hp 3.6L V6
- Exterior color:
- Firecracker Red Clearcoat (DISC)
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 25,484
- Stock #:
- P2294
- VIN:
- 1C6RJTEG1TL150219
New arrival
Sponsored Listing
2026 Jeep Gladiator
Mojave X Crew Cab 4WD
25,484 mi
Oak Lawn, IL
12 mi away
Fair Deal
$48,407
- Year:
- 2026
- Make:
- Jeep
- Model:
- Gladiator
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 285 hp 3.6L V6
- Exterior color:
- White
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 12,121
- Stock #:
- 29147705
- VIN:
- 1C6RJTBG4TL164569
2026 Jeep Gladiator
Rubicon Crew Cab 4WD
12,121 mi
Store transfer to Oak Lawn, IL
Price includes $749 shipping
Fair Deal
$44,747
- Year:
- 2026
- Make:
- Jeep
- Model:
- Gladiator
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 285 hp 3.6L V6
- Exterior color:
- White
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 11,848
- Stock #:
- 29147710
- VIN:
- 1C6RJTBG8TL157186
2026 Jeep Gladiator
Rubicon Crew Cab 4WD
11,848 mi
Store transfer to Oak Lawn, IL
Price includes $699 shipping
Good Deal
$44,697
- Year:
- 2026
- Make:
- Jeep
- Model:
- Gladiator
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 285 hp 3.6L V6
- Exterior color:
- Firecracker Red Clearcoat (DISC)
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 25,484
- Stock #:
- P2294
- VIN:
- 1C6RJTEG1TL150219
New arrival
2026 Jeep Gladiator
Mojave X Crew Cab 4WD
25,484 mi
Oak Lawn, IL
12 mi away
Fair Deal
$48,407
- Year:
- 2026
- Make:
- Jeep
- Model:
- Gladiator
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 285 hp 3.6L V6
- Exterior color:
- 41
- Fuel type:
- Gasoline
- Interior color:
- Brown (Heritage Tan/Black)
- Transmission:
- 8-Speed Automatic
- Mileage:
- 79
- Stock #:
- D260948A
- VIN:
- 1C6PJTAG3TL175460
2026 Jeep Gladiator
Willys '41 4dr Crew Cab 4WD
79 mi
Forest Park, IL
10 mi away
Fair Deal
$49,655
- Year:
- 2026
- Make:
- Jeep
- Model:
- Gladiator
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 285 hp 3.6L V6
- Exterior color:
- White
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 7,628
- Stock #:
- 151562
- VIN:
- 1C6RJTBG2TL151562
2026 Jeep Gladiator
Rubicon Crew Cab 4WD
7,628 mi
Hammond, IN
22 mi away
Great Deal
$41,194
- Year:
- 2026
- Make:
- Jeep
- Model:
- Gladiator
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 285 hp 3.6L V6
- Exterior color:
- Gray
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 224
- Stock #:
- 29079913
- VIN:
- 1C6RJTBG2TL166305
2026 Jeep Gladiator
Rubicon Crew Cab 4WD
224 mi
Store transfer to Oak Lawn, IL
Price includes $1,199 shipping
Great Deal
$48,197
- Year:
- 2026
- Make:
- Jeep
- Model:
- Gladiator
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 285 hp 3.6L V6
- Exterior color:
- Red
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 14,319
- Stock #:
- 29102449
- VIN:
- 1C6RJTBG5TL155962
New arrival
2026 Jeep Gladiator
Rubicon Crew Cab 4WD
14,319 mi
Store transfer to Oak Lawn, IL
Price includes $399 shipping
Fair Deal
$43,397
- Year:
- 2026
- Make:
- Jeep
- Model:
- Gladiator
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 285 hp 3.6L V6
- Exterior color:
- Black
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 14,221
- Stock #:
- 28933472
- VIN:
- 1C6RJTEG0TL153497
Price drop
-$1,000
2026 Jeep Gladiator
Mojave Crew Cab 4WD
14,221 mi
Store transfer to Oak Lawn, IL
Price includes $1,899 shipping
Good Deal
$44,897
$43,897
- Year:
- 2026
- Make:
- Jeep
- Model:
- Gladiator
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 285 hp 3.6L V6
- Exterior color:
- Gray
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 11,382
- Stock #:
- 29111921
- VIN:
- 1C6RJTBG1TL160611
2026 Jeep Gladiator
Rubicon Crew Cab 4WD
11,382 mi
Store transfer to Oak Lawn, IL
Price includes $1,099 shipping
Fair Deal
$45,097
- Year:
- 2026
- Make:
- Jeep
- Model:
- Gladiator
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 285 hp 3.6L V6
- Exterior color:
- White
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 10,639
- Stock #:
- 29145257
- VIN:
- 1C6RJTBGXTL163877
New arrival
2026 Jeep Gladiator
Rubicon Crew Cab 4WD
10,639 mi
Store transfer to Oak Lawn, IL
Price includes $1,099 shipping
Fair Deal
$45,097
- Year:
- 2026
- Make:
- Jeep
- Model:
- Gladiator
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 285 hp 3.6L V6
- Exterior color:
- Gray
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 929
- Stock #:
- 28958415
- VIN:
- 1C6RJTEG3TL159147
New arrival
2026 Jeep Gladiator
Mojave Crew Cab 4WD
929 mi
Store transfer to Oak Lawn, IL
Price includes $999 shipping
Fair Deal
$49,997
- Year:
- 2026
- Make:
- Jeep
- Model:
- Gladiator
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 285 hp 3.6L V6
- Exterior color:
- White
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 16,012
- Stock #:
- 28865209
- VIN:
- 1C6RJTBG9TL157472
2026 Jeep Gladiator
Rubicon Crew Cab 4WD
16,012 mi
Store transfer to Oak Lawn, IL
Price includes $1,899 shipping
Fair Deal
$43,897
- Year:
- 2026
- Make:
- Jeep
- Model:
- Gladiator
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 285 hp 3.6L V6
- Exterior color:
- Anvil Clearcoat
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 10
- Stock #:
- 262913
- VIN:
- 1C6RJTEG6TL192577
2026 Jeep Gladiator
Mojave X Crew Cab 4WD
Skokie, IL
11 mi away
New car
MSRP $63,800
$51,452
- Year:
- 2026
- Make:
- Jeep
- Model:
- Gladiator
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 285 hp 3.6L V6
- Exterior color:
- Gray
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 13
- Stock #:
- TL169674
- VIN:
- 1C6RJTBG4TL169674
2026 Jeep Gladiator
Rubicon X Crew Cab 4WD
Valparaiso, IN
40 mi away
New car
MSRP $63,905
$53,671
- Year:
- 2026
- Make:
- Jeep
- Model:
- Gladiator
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 285 hp 3.6L V6
- Exterior color:
- Hydro Blue Pearlcoat
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 8
- Stock #:
- D260471
- VIN:
- 1C6PJTAG6TL175226
2026 Jeep Gladiator
Sahara Crew Cab 4WD
Forest Park, IL
10 mi away
New car
MSRP $50,315
$39,321
- Year:
- 2026
- Make:
- Jeep
- Model:
- Gladiator
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 285 hp 3.6L V6
- Exterior color:
- Reign
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 10
- Stock #:
- J1296
- VIN:
- 1C6PJTAG1TL183203
2026 Jeep Gladiator
Willys '41 4dr Crew Cab 4WD
Crystal Lake, IL
43 mi away
New car
MSRP $55,575
$45,984
- Year:
- 2026
- Make:
- Jeep
- Model:
- Gladiator
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 285 hp 3.6L V6
- Exterior color:
- Anvil Clearcoat
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 13
- Stock #:
- LE5579
- VIN:
- 1C6PJTAG9TL168531
New arrival
2026 Jeep Gladiator
Sahara Crew Cab 4WD
Chesterton, IN
36 mi away
New car
MSRP $50,880
$40,826
- Year:
- 2026
- Make:
- Jeep
- Model:
- Gladiator
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 285 hp 3.6L V6
- Exterior color:
- Reign
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 11
- Stock #:
- D260476
- VIN:
- 1C6PJTAG8TL177575
2026 Jeep Gladiator
Sahara Crew Cab 4WD
Forest Park, IL
10 mi away
New car
MSRP $51,210
$39,417
- Year:
- 2026
- Make:
- Jeep
- Model:
- Gladiator
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 285 hp 3.6L V6
- Exterior color:
- Anvil Clearcoat
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 10
- Stock #:
- J4066
- VIN:
- 1C6RJTBG6TL186704
2026 Jeep Gladiator
Rubicon Crew Cab 4WD
Oak Lawn, IL
12 mi away
New car
MSRP $64,400
$52,983
- Year:
- 2026
- Make:
- Jeep
- Model:
- Gladiator
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 285 hp 3.6L V6
- Exterior color:
- Anvil Clearcoat
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 24
- Stock #:
- 260375
- VIN:
- 1C6PJTAG3TL175068
Price drop
-$1,500
2026 Jeep Gladiator
Sport S Crew Cab 4WD
Schaumburg, IL
26 mi away
New car
MSRP $53,310
$45,112
$43,612
- Year:
- 2026
- Make:
- Jeep
- Model:
- Gladiator
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 285 hp 3.6L V6
- Exterior color:
- Bright White Clearcoat
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 10
- Stock #:
- J4064
- VIN:
- 1C6RJTEG6TL186701
2026 Jeep Gladiator
Mojave X Crew Cab 4WD
Oak Lawn, IL
12 mi away
New car
MSRP $64,925
$53,448
- Year:
- 2026
- Make:
- Jeep
- Model:
- Gladiator
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 285 hp 3.6L V6
- Exterior color:
- Red Clearcoat
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Stock #:
- J41990
- VIN:
- 1C6PJTAGXTL155612
2026 Jeep Gladiator
Sport S Crew Cab 4WD
Tinley Park, IL
22 mi away
New car
MSRP $56,260
$44,316
2027 Jeep Gladiator Trims
| Trim type | MSRP |
|---|---|
| Rubicon X Crew Cab 4WD | -- |
| Rubicon Crew Cab 4WD | -- |
*CarGurus meticulously monitors the prices of millions of pre-owned vehicle listings, offering users precise and up-to-date market insights. Historical pricing data excludes any additional dealer fees as of May 3, 2026.
2027 Jeep Gladiator Price Trends
CarGurus tracks the prices of millions of used car listings every year. See how the average price of 2027 Jeep Gladiator prices has changed over time.
See more price trendsAVG Price
Not Available
2027 Jeep Gladiator
Index Price
$29,119
0.2%
All used vehicles
2027 Jeep Gladiator Pricing Analysis: Chicago, IL Market Report
Pricing Analysis by Model Year
Key Insights
- Newer Models Command Premiums: The 2026 Gladiator is priced at $44,624, which is 13.3% above its MSRP, indicating strong demand for the latest model.
- Significant Depreciation for Older Models: The 2020 Gladiator shows the steepest decline, priced at $28,893, which is -13.5% compared to its original MSRP.
- Best Value in Mid-Range Models: The 2025 Gladiator is priced at $37,685, only -8.3% below MSRP, making it a potentially attractive option for buyers seeking value.
Model Year Pricing
| Model Year | Original MSRP | Avg Price | Price vs MSRP |
|---|---|---|---|
| 2026 Jeep Gladiator | $39,300 | $44,624 | +13.3% |
| 2025 Jeep Gladiator | $38,100 | $37,685 | -1.1% |
| 2024 Jeep Gladiator | $37,895 | $38,778 | +2.3% |
| 2023 Jeep Gladiator | $38,990 | $34,778 | -10.8% |
| 2022 Jeep Gladiator | $37,170 | $30,422 | -18.1% |
| 2021 Jeep Gladiator | $34,645 | $32,081 | -7.4% |
| 2020 Jeep Gladiator | $33,545 | $28,893 | -13.5% |
These recommendations are based on CarGurus' proprietary market data from August 27, 2026, CarGurus experts' opinions, and generative AI.
*CarGurus meticulously monitors the prices of millions of pre-owned vehicle listings, offering users precise and up-to-date market insights. Historical pricing data excludes any additional dealer fees as of May 3, 2026.
FAQs
How many 2027 Jeep Gladiator vehicles in Chicago, IL have no reported accidents or damage?
48 out of 48 for sale near Chicago, IL have no reported accidents or damage.
What is the fuel economy of the 2027 Jeep Gladiator?
Depending on the engine and options, the 2027 Jeep Gladiator gets between 19 and 19 MPG (or EV battery range).
What fuel types are available?
Gasoline engines are available.
*CarGurus meticulously monitors the prices of millions of pre-owned vehicle listings, offering users precise and up-to-date market insights. Historical pricing data excludes any additional dealer fees as of May 3, 2026.
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