7 photos $19,990
$20,555 below MSRP
2020 Jeep Grand Cherokee Altitude
Gray · 4WD
65,595 mi · Highland, IN
No accidents reported 2 owners Lease
Carvana
FOR SALE · CHICAGO, IL
Jeep Grand Cherokee for sale in Chicago
There are 20 Jeep Grand Cherokees for sale near Chicago right now, running $19,990 to $57,567, median around $49,698. Here they are, plus the free safety record before you commit to one.
Range
$19,990–$57,567
Median
$49,698
Listings
20
7 photos 
25 photos $57,567
$3,033 below MSRP
2026 Jeep Grand Cherokee Summit
White · 4WD
Crystal Lake, IL
Al Piemonte Chrysler Dodge Jeep RAM
27 photos $54,371
$6,229 below MSRP
2026 Jeep Grand Cherokee Summit
White · 4WD
2,218 mi · Crystal Lake, IL
Al Piemonte Chrysler Dodge Jeep RAM
42 photos $51,719
2026 Jeep Grand Cherokee 85th Anniversary Edition
Blue · 4WD
18 mi · Cedar Lake, IN
James CDJR Cedar Lake
43 photos $51,992
2026 Jeep Grand Cherokee 85th Anniversary Edition
Black · 4WD
29 mi · Cedar Lake, IN
James CDJR Cedar Lake
41 photos $50,747
2025 Jeep Grand Cherokee Limited
Gray · 4WD
232 mi · Cedar Lake, IN
James CDJR Cedar Lake
$51,513
2026 Jeep Grand Cherokee 85th Anniversary Edition
Blue · 4WD
17 mi · Hampshire, IL
James Chrysler Dodge Jeep Ram
35 photos $50,496
2026 Jeep Grand Cherokee 85th Anniversary Edition
Blue · 4WD
Elmhurst, IL
Elmhurst Chrysler Jeep Dodge Ram
42 photos $50,509
$1,406 below MSRP
2026 Jeep Grand Cherokee Limited Reserve
Black · 4WD
16 mi · Cedar Lake, IN
James CDJR Cedar Lake
25 photos $49,698
$717 below MSRP
2026 Jeep Grand Cherokee 85th Anniversary Edition
Silver · 4WD
11 mi · Merrillville, IN
Team CDJR on 30
35 photos $49,792
$623 below MSRP
2026 Jeep Grand Cherokee 85th Anniversary Edition
White · 4WD
10 mi · Elmhurst, IL
Elmhurst Chrysler Jeep Dodge Ram
$49,513
$902 below MSRP
2026 Jeep Grand Cherokee 85th Anniversary Edition
Gray · 4WD
17 mi · Hampshire, IL
James Chrysler Dodge Jeep Ram
24 photos $46,698
$3,717 below MSRP
2026 Jeep Grand Cherokee 85th Anniversary Edition
Red · 4WD
32 mi · Merrillville, IN
Team CDJR on 30
24 photos $46,278
$4,137 below MSRP
2026 Jeep Grand Cherokee 85th Anniversary Edition
Blue · 4WD
2 mi · Merrillville, IN
Team CDJR on 30
28 photos $45,998
$22,942 below MSRP
2023 Jeep Grand Cherokee Summit Reserve
Black · 4WD
14,795 mi · Hillside, IL
CarMax Hillside (Eisenhower Expy)
$45,013
$5,402 below MSRP
2026 Jeep Grand Cherokee 85th Anniversary Edition
Blue · 4WD
13 mi · Hampshire, IL
James Chrysler Dodge Jeep Ram
26 photos $45,101
$5,314 below MSRP
2026 Jeep Grand Cherokee 85th Anniversary Edition
4WD
200 mi · Merrillville, IN
Team CDJR on 30
26 photos $45,512
$4,903 below MSRP
2026 Jeep Grand Cherokee 85th Anniversary Edition
Gray · 4WD
Crystal Lake, IL
Al Piemonte Chrysler Dodge Jeep RAM
$44,958
$1,402 below MSRP
2026 Jeep Grand Cherokee Laredo Altitude
White · 4WD
12 mi · Hampshire, IL
James Chrysler Dodge Jeep Ram
40 photos $44,589
$1,771 below MSRP
2026 Jeep Grand Cherokee Laredo Altitude
Black · 4WD
7 mi · Cedar Lake, IN
James CDJR Cedar Lake
Listings via Auto.dev, as of July 16, 2026. Prices and availability change, confirm with the seller.
BEFORE YOU BUY ONE OF THESE
Check the free safety record first
Every JeepGrand Cherokee has its own model-year safety record: open NHTSA recalls, owner complaints, crash-test ratings, and EPA fuel cost. Free, no account, before you message a seller.
See the free Jeep Grand Cherokee record by year →ALSO FOR SALE IN CHICAGO
JeepGrand Cherokee FOR SALE ELSEWHERE