Jeep Grand Cherokee for sale in Chicago, IL
Listings from dealers with a Chicago, IL address.
As of November 4, 2026, OAV tracks 256 Jeep Grand Cherokee listings from 59 dealers with a Chicago, IL address: 158 used, listed from $2,995 to $64,995, and 98 new, listed from $35,424 to $65,158.
Ratings: 4 Great Deal, 153 Fair Price, 6 Overpriced. Unscored: 93.
Market snapshot · November 4, 2026
Jeep Grand Cherokee listed prices by model year in Chicago
| Model year | Condition | Listings | Listed price range |
|---|---|---|---|
| 2027 | New | 82 | $42,403–$65,158 |
| 2026 | New | 16 | $35,424–$53,273 |
| 2026 | Used | 3 | $32,500–$49,580 |
| 2025 | Used | 21 | $25,500–$48,294 |
| 2024 | Used | 9 | $19,877–$42,407 |
| 2023 | Used | 19 | $19,927–$38,000 |
| 2022 | Used | 5 | $21,995–$35,994 |
| 2021 | Used | 4 | $15,708–$23,694 |
| 2020 | Used | 12 | $12,989–$32,995 |
| 2019 | Used | 7 | $10,995–$29,995 |
| 2018 | Used | 15 | $11,995–$64,995 |
| 2017 | Used | 12 | $9,499–$27,995 |
| 2016 | Used | 4 | $9,810–$13,500 |
| 2015 | Used | 10 | $6,995–$14,995 |
| 2014 | Used | 16 | $6,995–$13,995 |
| 2013 | Used | 3 | $7,999–$10,360 |
| 2012 | Used | 8 | $6,850–$10,896 |
| 2011 | Used | 6 | $9,896–$12,850 |
| 2010 | Used | 1 | — |
| 2006 | Used | 1 | — |
| 2005 | Used | 1 | — |
| 1997 | Used | 1 | — |
Showing the first 50 of 256 listings, ordered by model year, newest first, then listed price, lowest first.
- 2027 Jeep Grand Cherokee Laredo · Mileage not verified · $42,403 · Fair Price · Listed by Marino Chrysler Jeep Dodge Ram
- 2027 Jeep Grand Cherokee Laredo · Mileage not verified · $42,403 · Fair Price · Listed by Marino Chrysler Jeep Dodge Ram
- 2027 Jeep Grand Cherokee Laredo · Mileage not verified · $42,998 · Fair Price · Listed by Marino Chrysler Jeep Dodge Ram
- 2027 Jeep Grand Cherokee Laredo · Mileage not verified · $42,998 · Fair Price · Listed by Marino Chrysler Jeep Dodge Ram
- 2027 Jeep Grand Cherokee Laredo · Mileage not verified · $42,998 · Fair Price · Listed by Marino Chrysler Jeep Dodge Ram
- 2027 Jeep Grand Cherokee Laredo · 11 mi · $43,138 · Fair Price · Listed by Dial Chrysler Dodge Jeep Ram
- 2027 Jeep Grand Cherokee Laredo · Mileage not verified · $43,403 · Fair Price · Listed by Marino Chrysler Jeep Dodge Ram
- 2027 Jeep Grand Cherokee Laredo · 12 mi · $43,413 · Fair Price · Listed by Dial Chrysler Dodge Jeep Ram
- 2027 Jeep Grand Cherokee Laredo · Mileage not verified · $43,998 · Fair Price · Listed by Marino Chrysler Jeep Dodge Ram
- 2027 Jeep Grand Cherokee Laredo · Mileage not verified · $43,998 · Fair Price · Listed by Marino Chrysler Jeep Dodge Ram
- 2027 Jeep Grand Cherokee Laredo · Mileage not verified · $43,998 · Fair Price · Listed by Marino Chrysler Jeep Dodge Ram
- 2027 Jeep Grand Cherokee Laredo · Mileage not verified · $44,283 · Fair Price · Listed by Marino Chrysler Jeep Dodge Ram
- 2027 Jeep Grand Cherokee Laredo · Mileage not verified · $44,688 · Fair Price · Listed by Marino Chrysler Jeep Dodge Ram
- 2027 Jeep Grand Cherokee Laredo · 11 mi · $45,018 · Fair Price · Listed by Dial Chrysler Dodge Jeep Ram
- 2027 Jeep Grand Cherokee Laredo · Mileage not verified · $45,283 · Fair Price · Listed by Marino Chrysler Jeep Dodge Ram
- 2027 Jeep Grand Cherokee Laredo · 18 mi · $45,628 · Fair Price · Listed by Chrysler Dodge Jeep Ram of Chicago
- 2027 Jeep Grand Cherokee Laredo · Mileage not verified · $45,893 · Fair Price · Listed by Marino Chrysler Jeep Dodge Ram
- 2027 Jeep Grand Cherokee Laredo · Mileage not verified · $45,893 · Fair Price · Listed by Marino Chrysler Jeep Dodge Ram
- 2027 Jeep Grand Cherokee Laredo · 13 mi · $46,018 · Fair Price · Listed by Dial Chrysler Dodge Jeep Ram
- 2027 Jeep Grand Cherokee Laredo · Mileage not verified · $46,193 · Fair Price · Listed by Marino Chrysler Jeep Dodge Ram
- 2027 Jeep Grand Cherokee Laredo · 9 mi · $46,223 · Fair Price · Listed by Dial Chrysler Dodge Jeep Ram
- 2027 Jeep Grand Cherokee Laredo · 10 mi · $46,223 · Fair Price · Listed by Dial Chrysler Dodge Jeep Ram
- 2027 Jeep Grand Cherokee Laredo · Mileage not verified · $46,488 · Fair Price · Listed by Marino Chrysler Jeep Dodge Ram
- 2027 Jeep Grand Cherokee Laredo · Mileage not verified · $46,488 · Fair Price · Listed by Marino Chrysler Jeep Dodge Ram
- 2027 Jeep Grand Cherokee Laredo · Mileage not verified · $46,488 · Fair Price · Listed by Marino Chrysler Jeep Dodge Ram
- 2027 Jeep Grand Cherokee Laredo · Mileage not verified · $46,488 · Fair Price · Listed by Marino Chrysler Jeep Dodge Ram
- 2027 Jeep Grand Cherokee Laredo · Mileage not verified · $46,888 · Fair Price · Listed by Marino Chrysler Jeep Dodge Ram
- 2027 Jeep Grand Cherokee Limited · 15 mi · $47,362 · Fair Price · Listed by City Auto Group
- 2027 Jeep Grand Cherokee Laredo · Mileage not verified · $47,483 · Fair Price · Listed by Marino Chrysler Jeep Dodge Ram
- 2027 Jeep Grand Cherokee Laredo · Mileage not verified · $47,483 · Fair Price · Listed by Marino Chrysler Jeep Dodge Ram
- 2027 Jeep Grand Cherokee Laredo · Mileage not verified · $47,488 · Fair Price · Listed by Marino Chrysler Jeep Dodge Ram
- 2027 Jeep Grand Cherokee Laredo · Mileage not verified · $47,715 · Fair Price · Listed by Marino Chrysler Jeep Dodge Ram
- 2027 Jeep Grand Cherokee Limited · 18 mi · $47,733 · Fair Price · Listed by City Auto Group
- 2027 Jeep Grand Cherokee Limited · Mileage not verified · $48,046 · Fair Price · Listed by Marino Chrysler Jeep Dodge Ram
- 2027 Jeep Grand Cherokee Limited · 5 mi · $48,344 · Fair Price · Listed by City Auto Group
- 2027 Jeep Grand Cherokee Laredo · Mileage not verified · $48,510 · Fair Price · Listed by Marino Chrysler Jeep Dodge Ram
- 2027 Jeep Grand Cherokee Limited · Mileage not verified · $48,551 · Fair Price · Listed by Marino Chrysler Jeep Dodge Ram
- 2027 Jeep Grand Cherokee Limited · Mileage not verified · $48,551 · Fair Price · Listed by Marino Chrysler Jeep Dodge Ram
- 2027 Jeep Grand Cherokee Limited · Mileage not verified · $48,551 · Fair Price · Listed by Marino Chrysler Jeep Dodge Ram
- 2027 Jeep Grand Cherokee Limited · 12 mi · $48,798 · Fair Price · Listed by City Auto Group
- 2027 Jeep Grand Cherokee Limited · Mileage not verified · $48,894 · Fair Price · Listed by Marino Chrysler Jeep Dodge Ram
- 2027 Jeep Grand Cherokee Limited · 11 mi · $48,913 · Fair Price · Listed by Dial Chrysler Dodge Jeep Ram
- 2027 Jeep Grand Cherokee Limited · 19 mi · $48,930 · Fair Price · Listed by City Auto Group
- 2027 Jeep Grand Cherokee Limited · Mileage not verified · $49,046 · Fair Price · Listed by Marino Chrysler Jeep Dodge Ram
- 2027 Jeep Grand Cherokee Limited · 13 mi · $49,128 · Fair Price · Listed by Chrysler Dodge Jeep Ram of Chicago
- 2027 Jeep Grand Cherokee Laredo · 10 mi · $49,173 · Fair Price · Listed by Dial Chrysler Dodge Jeep Ram
- 2027 Jeep Grand Cherokee Laredo · 10 mi · $49,173 · Fair Price · Listed by Dial Chrysler Dodge Jeep Ram
- 2027 Jeep Grand Cherokee Limited · Mileage not verified · $49,399 · Fair Price · Listed by Marino Chrysler Jeep Dodge Ram
- 2027 Jeep Grand Cherokee Limited · Mileage not verified · $49,609 · Fair Price · Listed by Marino Chrysler Jeep Dodge Ram
- 2027 Jeep Grand Cherokee Limited · 15 mi · $49,723 · Fair Price · Listed by Dial Chrysler Dodge Jeep Ram
- How many Jeep Grand Cherokee listings are for sale in Chicago, IL?
- As of November 4, 2026, OAV tracks 256 Jeep Grand Cherokee listings from 59 dealers with a Chicago, IL address: 158 used, listed from $2,995 to $64,995, and 98 new, listed from $35,424 to $65,158. Ratings: 4 Great Deal, 153 Fair Price, 6 Overpriced. Unscored: 93.
- What does a used Jeep Grand Cherokee cost in Chicago, IL?
- Used Jeep Grand Cherokee listings in Chicago, IL are listed from $2,995 to $64,995 as of November 4, 2026. By model year: 2025: $25,500–$48,294 (21 listings); 2023: $19,927–$38,000 (19 listings); 2014: $6,995–$13,995 (16 listings).
- How does OAV rate Jeep Grand Cherokee listings in Chicago?
- OAV rates scored listings as Great Deal (priced below the comparable-range floor by at least OAV's minimum-gap margin), Fair Price (priced within the comparable range, or below the floor by less than that margin), or Overpriced (priced above the comparable range). Listings OAV cannot score on the available evidence are shown as Unscored rather than receiving an unsupported verdict.