New & Used 2027 Jeep Gladiator for Sale nearWinnetka, IL
190 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
17 mi away
Great Deal
$42,027
- 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:
- 18,955
- Stock #:
- SH3698S
- VIN:
- 1C6RJTBG1TL160544
Sponsored Listing
2026 Jeep Gladiator
Rubicon Crew Cab 4WD
18,955 mi
Schaumburg, IL
15 mi away
Fair Deal
$40,500
- 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 Clearcoat
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 3,271
- Stock #:
- G5497A
- VIN:
- 1C6PJTAG9TL168853
Sponsored Listing
2026 Jeep Gladiator
Sahara Crew Cab 4WD
3,271 mi
Lincolnwood, IL
7 mi away
Good Deal
$40,400
- 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 Clearcoat
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 14,490
- Stock #:
- Z5672
- VIN:
- 1C6RJTBG8TL164994
New arrival
2026 Jeep Gladiator
Rubicon Crew Cab 4WD
14,490 mi
Riverside, IL
18 mi away
Good Deal
$38,994
- 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 Clearcoat
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 3,271
- Stock #:
- G5497A
- VIN:
- 1C6PJTAG9TL168853
2026 Jeep Gladiator
Sahara Crew Cab 4WD
3,271 mi
Lincolnwood, IL
7 mi away
Good Deal
$40,400
- 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
17 mi away
Great Deal
$42,027
- 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
Price drop
-$4,559
2026 Jeep Gladiator
Mojave X Crew Cab 4WD
25,484 mi
Oak Lawn, IL
27 mi away
Great Deal
$45,831
$41,272
- 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:
- 18,955
- Stock #:
- SH3698S
- VIN:
- 1C6RJTBG1TL160544
2026 Jeep Gladiator
Rubicon Crew Cab 4WD
18,955 mi
Schaumburg, IL
15 mi away
Fair Deal
$40,500
- 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:
- Green
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 1,727
- Stock #:
- 29255515
- VIN:
- 1C6PJTAG2TL167270
2026 Jeep Gladiator
Sport Crew Cab 4WD
1,727 mi
Store transfer to Glencoe, IL
Price includes $699 shipping
Fair Deal
$38,697
- 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:
- White
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 14,675
- Stock #:
- 28783537
- VIN:
- 1C6RJTEG0TL164953
2026 Jeep Gladiator
Mojave Crew Cab 4WD
14,675 mi
Store transfer to Glencoe, IL
Price includes $699 shipping
Fair Deal
$41,697
- 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:
- White
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 9,400
- Stock #:
- 151562
- VIN:
- 1C6RJTBG2TL151562
Price drop
-$1,000
2026 Jeep Gladiator
Rubicon Crew Cab 4WD
9,400 mi
Hammond, IN
39 mi away
Great Deal
$39,194
$38,194
- 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:
- White
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 18,685
- Stock #:
- 29183098
- VIN:
- 1C6RJTBG5TL157291
New arrival
2026 Jeep Gladiator
Rubicon Crew Cab 4WD
18,685 mi
Store transfer to Glencoe, IL
Price includes $399 shipping
Good Deal
$39,397
- 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:
- Gray
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 16,515
- Stock #:
- 29204701
- VIN:
- 1C6RJTBG0TL162446
2026 Jeep Gladiator
Rubicon Crew Cab 4WD
16,515 mi
Store transfer to Glencoe, IL
Price includes $749 shipping
Fair Deal
$41,747
- 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:
- Gray
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 246
- Stock #:
- 29079913
- VIN:
- 1C6RJTBG2TL166305
2026 Jeep Gladiator
Rubicon Crew Cab 4WD
246 mi
Store transfer to Glencoe, IL
Price includes $399 shipping
Great Deal
$46,397
- 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:
- White
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray
- Transmission:
- Automatic
- Mileage:
- 16,006
- Stock #:
- 29185645
- VIN:
- 1C6RJTBG5TL157470
2026 Jeep Gladiator
Rubicon Crew Cab 4WD
16,006 mi
Store transfer to Glencoe, IL
Price includes $1,899 shipping
Fair Deal
$41,897
- 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:
- Black
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 18,684
- Stock #:
- 29239753
- VIN:
- 1C6RJTBG4TL163907
Price drop
-$1,000
2026 Jeep Gladiator
Rubicon Crew Cab 4WD
18,684 mi
Store transfer to Glencoe, IL
Price includes $449 shipping
Good Deal
$40,447
$39,447
- 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:
- 2,456
- Stock #:
- 28880203
- VIN:
- 1C6PJTAGXTL171230
2026 Jeep Gladiator
Sport Crew Cab 4WD
2,456 mi
Store transfer to Glencoe, IL
Price includes $1,399 shipping
Fair Deal
$38,397
- 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:
- Red
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 15,248
- Stock #:
- 29147715
- VIN:
- 1C6RJTBG4TL157542
2026 Jeep Gladiator
Rubicon Crew Cab 4WD
15,248 mi
Store transfer to Glencoe, IL
Price includes $749 shipping
Fair Deal
$41,747
- 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:
- Black
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 267
- Stock #:
- 29069567
- VIN:
- 1C6RJTAG0TL181550
2026 Jeep Gladiator
Sport S Crew Cab 4WD
267 mi
Store transfer to Glencoe, IL
Price includes $1,899 shipping
Good Deal
$39,897
- 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:
- Gray
- Transmission:
- Automatic
- Mileage:
- 16,952
- Stock #:
- 29147156
- VIN:
- 1C6RJTBG4TL150929
2026 Jeep Gladiator
Rubicon Crew Cab 4WD
16,952 mi
Store transfer to Glencoe, IL
Price includes $799 shipping
Fair Deal
$41,797
- 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:
- 14,227
- Stock #:
- 28933472
- VIN:
- 1C6RJTEG0TL153497
2026 Jeep Gladiator
Mojave Crew Cab 4WD
14,227 mi
Store transfer to Glencoe, IL
Price includes $1,899 shipping
Fair Deal
$41,897
- 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:
- White
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray
- Transmission:
- Automatic
- Mileage:
- 17,541
- Stock #:
- 29204583
- VIN:
- 1C6RJTBG7TL151105
2026 Jeep Gladiator
Rubicon Crew Cab 4WD
17,541 mi
Store transfer to Glencoe, IL
Price includes $749 shipping
Fair Deal
$40,747
- 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:
- Black
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 16,068
- Stock #:
- 29176291
- VIN:
- 1C6RJTEG5TL164382
2026 Jeep Gladiator
Mojave Crew Cab 4WD
16,068 mi
Store transfer to Glencoe, IL
Price includes $1,099 shipping
Fair Deal
$42,097
- 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:
- 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
Price drop
-$4,559
Sponsored Listing
2026 Jeep Gladiator
Mojave X Crew Cab 4WD
25,484 mi
Oak Lawn, IL
27 mi away
Great Deal
$45,831
$41,272
2027 Jeep Gladiator Trims
| Trim type | MSRP |
|---|---|
| Sahara Crew Cab 4WD | $48,400 |
| Rewind 4dr Crew Cab 4WD | $51,540 |
| Rubicon X Crew Cab 4WD | $64,995 |
| Rubicon Crew Cab 4WD | $55,700 |
| Mojave X Crew Cab 4WD | $63,295 |
| Mojave Crew Cab 4WD | $56,200 |
| Willys Crew Cab 4WD | $47,445 |
| Sport S Crew Cab 4WD | $42,100 |
*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
$28,695
1.0%
All used vehicles
2027 Jeep Gladiator Pricing Analysis
Pricing Analysis by Model Year
Key Insights
- New-Car Premium: The 2026 model year shows a significant average price of $45,473, indicating a 15.7% premium over its starting MSRP.
- Steepest Depreciation: The 2020 model year has experienced the steepest depreciation at -15.4%, reflecting a notable decline in value.
- Years Priced Above Starting MSRP: The 2026 and 2025 model years are priced above their starting MSRPs, suggesting strong demand for newer models.
Model Year Pricing
| Model Year | Starting MSRP | Avg Price | Avg Price vs Starting MSRP |
|---|---|---|---|
| 2026 | $39,300 | $45,473 | +15.7% |
| 2025 | $38,100 | $40,442 | +6.1% |
| 2024 | $37,895 | $37,674 | -0.6% |
| 2023 | $38,990 | $34,443 | -11.7% |
| 2022 | $37,170 | $31,644 | -14.9% |
| 2021 | $34,645 | $30,998 | -10.5% |
| 2020 | $33,545 | $28,378 | -15.4% |
These recommendations are based on CarGurus' proprietary market data from October 14, 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 Winnetka, IL have no reported accidents or damage?
69 out of 69 for sale near Winnetka, 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/MPGe.
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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