AI-Assisted Car Shopping

 New Search
Save
Sort

Used 2021 Jeep Grand Cherokee for Sale in Chicago, IL

Grand Cherokees for Sale at Dealers, Ranked by CoPilot AI ?

Filters
Price
Year
Mileage
Trim
2021 Jeep Grand Cherokee Laredo X 4WD photo
1
Price Drop
Jeep Grand Cherokee Laredo X 4WD Streamwood, IL
$26,490 30.9k miles
•••

#1 2021 Jeep Grand Cherokee

CoPilot AI: It’s anA+” Buy

  • $500 Price Drop
  • Great Price - $3,500 Below Market
  • Includes $5,572 Premium Upgrades
See more about this car
2021 Jeep Grand Cherokee Limited 4WD photo
2
Jeep Grand Cherokee Limited 4WD Fox Lake, IL
$31,787 21.3k miles
•••

#2 2021 Jeep Grand Cherokee

CoPilot AI: It’s anA+” Buy

  • Great Price - $3,426 Below Market
  • Includes $4,387 Premium Upgrades
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
2021 Jeep Grand Cherokee Freedom 4WD photo
3
Price Drop
Jeep Grand Cherokee Freedom 4WD Merrillville, IN
$29,813 19.9k miles
•••

#3 2021 Jeep Grand Cherokee

CoPilot AI: It’s anA+” Buy

  • $2,137 Price Drop
  • Great Price - $2,904 Below Market
  • Includes $6,035 Premium Upgrades
See more about this car
2021 Jeep Grand Cherokee 80th Anniversary 4WD photo
4
Price Drop
Jeep Grand Cherokee 80th Anniversary 4WD Chicago, IL
$30,875 27.4k miles
•••

#4 2021 Jeep Grand Cherokee

CoPilot AI: It’s anA+” Buy

  • $954 Price Drop
  • Great Price - $2,771 Below Market
  • Includes $3,023 Premium Upgrades
See more about this car
2021 Jeep Grand Cherokee Limited 4WD photo
5
Price Drop
Jeep Grand Cherokee Limited 4WD Elmhurst, IL
$30,303 26.6k miles
•••

#5 2021 Jeep Grand Cherokee

CoPilot AI: It’s anA+” Buy

  • $307 Price Drop
  • Great Price - $2,697 Below Market
  • Includes $1,990 Premium Upgrades
See more about this car
2021 Jeep Grand Cherokee Overland 4WD photo
6
Price Drop
Jeep Grand Cherokee Overland 4WD St. Charles, IL
$34,995 29.2k miles
•••

#6 2021 Jeep Grand Cherokee

CoPilot AI: It’s anA+” Buy

  • $1,000 Price Drop
  • Great Price - $2,355 Below Market
  • Includes $1,925 Premium Upgrades
See more about this car
2021 Jeep Grand Cherokee Laredo E 4WD photo
7
Jeep Grand Cherokee Laredo E 4WD Bourbonnais, IL
$26,900 25.2k miles
•••

#7 2021 Jeep Grand Cherokee

CoPilot AI: It’s anA+” Buy

  • Great Price - $2,093 Below Market
  • Includes $2,471 Premium Upgrades
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
2021 Jeep Grand Cherokee Laredo X 4WD photo
8
Jeep Grand Cherokee Laredo X 4WD Chicago, IL
$29,998 21.3k miles
•••

#8 2021 Jeep Grand Cherokee

CoPilot AI: It’s anA+” Buy

  • Great Price - $2,063 Below Market
  • Includes $5,936 Premium Upgrades
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
2021 Jeep Grand Cherokee 80th Anniversary 4WD photo
9
Price Drop
Jeep Grand Cherokee 80th Anniversary 4WD Arlington Heights, IL
$30,995 37.9k miles
•••

#9 2021 Jeep Grand Cherokee

CoPilot AI: It’s anA+” Buy

  • $500 Price Drop
  • Great Price - $1,998 Below Market
  • Includes $3,578 Premium Upgrades
See more about this car
2021 Jeep Grand Cherokee Limited 4WD photo
10
Jeep Grand Cherokee Limited 4WD Schaumburg, IL
$23,489 69.6k miles
•••

#10 2021 Jeep Grand Cherokee

CoPilot AI: It’s anA+” Buy

  • Great Price - $3,970 Below Market
  • Includes $1,746 Premium Upgrades
  • CARFAX: One Owner, Clean Title
See more about this car
2021 Jeep Grand Cherokee 80th Anniversary 4WD photo
11
Price Drop
Jeep Grand Cherokee 80th Anniversary 4WD Arlington Heights, IL
$26,582 49.1k miles Certified
•••

#11 2021 Jeep Grand Cherokee

CoPilot AI: It’s anA+” Buy

  • $413 Price Drop
  • Great Price - $3,662 Below Market
  • Includes $1,727 Premium Upgrades
See more about this car
2021 Jeep Grand Cherokee Summit 4WD photo
12
Price Drop
Jeep Grand Cherokee Summit 4WD Momence, IL
$39,665 40.7k miles
•••

#12 2021 Jeep Grand Cherokee

CoPilot AI: It’s anA+” Buy

  • $164 Price Drop
  • Great Price - $3,440 Below Market
  • Includes $7,924 Premium Upgrades
See more about this car
2021 Jeep Grand Cherokee Limited 4WD photo
13
Jeep Grand Cherokee Limited 4WD Palatine, IL
$31,609 5.6k miles
•••

#13 2021 Jeep Grand Cherokee

CoPilot AI: It’s anA+” Buy

  • Great Price - $2,662 Below Market
  • Includes $1,445 Premium Upgrades
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
2021 Jeep Grand Cherokee Laredo X 4WD photo
14
Price Drop
Jeep Grand Cherokee Laredo X 4WD Hodgkins, IL
$26,813 44.9k miles
•••

#14 2021 Jeep Grand Cherokee

CoPilot AI: It’s anA+” Buy

  • $569 Price Drop
  • Great Price - $2,591 Below Market
  • Includes $5,896 Premium Upgrades
See more about this car
2021 Jeep Grand Cherokee 80th Anniversary 4WD photo
15
Price Drop
Jeep Grand Cherokee 80th Anniversary 4WD Valparaiso, IN
$29,595 46k miles
•••

#15 2021 Jeep Grand Cherokee

CoPilot AI: It’s anA+” Buy

  • $400 Price Drop
  • Great Price - $2,348 Below Market
  • Includes $3,464 Premium Upgrades
See more about this car
2021 Jeep Grand Cherokee Limited 4WD photo
16
Jeep Grand Cherokee Limited 4WD Orland Park, IL
$30,900 20.2k miles
•••

#16 2021 Jeep Grand Cherokee

CoPilot AI: It’s anA+” Buy

  • Great Price - $2,140 Below Market
  • Includes $2,655 Premium Upgrades
  • CARFAX: Clean Title, Not a rental or commercial vehicle
See more about this car
2021 Jeep Grand Cherokee 80th Anniversary 4WD photo
17
Jeep Grand Cherokee 80th Anniversary 4WD Naperville, IL
$31,822 17.7k miles
•••

#17 2021 Jeep Grand Cherokee

CoPilot AI: It’s anA+” Buy

  • Great Price - $2,123 Below Market
  • Includes $1,748 Premium Upgrades
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
2021 Jeep Grand Cherokee Laredo X 4WD photo
18
Price Drop
Jeep Grand Cherokee Laredo X 4WD Oak Lawn, IL
$27,650 40.8k miles
•••

#18 2021 Jeep Grand Cherokee

CoPilot AI: It’s anA+” Buy

  • $100 Price Drop
  • Great Price - $2,075 Below Market
  • Includes $6,057 Premium Upgrades
See more about this car
2021 Jeep Grand Cherokee Trackhawk 4WD photo
19
Jeep Grand Cherokee Trackhawk 4WD Glenview, IL
$89,900 23.5k miles
•••

#19 2021 Jeep Grand Cherokee

CoPilot AI: It’s anA+” Buy

  • Good Price - $5,642 Below Market
  • Includes $5,672 Premium Upgrades
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
2021 Jeep Grand Cherokee Laredo E 4WD photo
20
Price Drop
Jeep Grand Cherokee Laredo E 4WD Tinley Park, IL
$23,585 49.5k miles
•••

#20 2021 Jeep Grand Cherokee

CoPilot AI: It’s anA+” Buy

  • $98 Price Drop
  • Great Price - $2,528 Below Market
  • Includes $2,137 Premium Upgrades
See more about this car
2021 Jeep Grand Cherokee 80th Anniversary 4WD photo
21
Jeep Grand Cherokee 80th Anniversary 4WD Bridgeview, IL
$33,500 28.1k miles
•••

#21 2021 Jeep Grand Cherokee

CoPilot AI: It’s anA+” Buy

  • Good Price - $2,113 Below Market
  • Includes $3,716 Premium Upgrades
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
2021 Jeep Grand Cherokee 80th Anniversary 4WD photo
22
Price Drop
Jeep Grand Cherokee 80th Anniversary 4WD Antioch, IL
$32,961 29k miles
•••

#22 2021 Jeep Grand Cherokee

CoPilot AI: It’s anA+” Buy

  • $270 Price Drop
  • Good Price - $2,083 Below Market
  • Includes $3,710 Premium Upgrades
See more about this car
2021 Jeep Grand Cherokee Trailhawk 4WD photo
23
Price Drop
Jeep Grand Cherokee Trailhawk 4WD Streamwood, IL
$32,490 28.6k miles
•••

#23 2021 Jeep Grand Cherokee

CoPilot AI: It’s anA+” Buy

  • $500 Price Drop
  • Good Price - $1,988 Below Market
  • Includes $2,026 Premium Upgrades
See more about this car
2021 Jeep Grand Cherokee Laredo X 4WD photo
24
Jeep Grand Cherokee Laredo X 4WD Elmhurst, IL
$29,002 40.7k miles
•••

#24 2021 Jeep Grand Cherokee

CoPilot AI: It’s anA+” Buy

  • Great Price - $1,957 Below Market
  • Includes $6,639 Premium Upgrades
  • CARFAX: Clean Title
See more about this car
2021 Jeep Grand Cherokee Limited 4WD photo
25
Price Drop
Jeep Grand Cherokee Limited 4WD Hodgkins, IL
$28,664 31.4k miles
•••

#25 2021 Jeep Grand Cherokee

CoPilot AI: It’s anA+” Buy

  • $307 Price Drop
  • Great Price - $1,868 Below Market
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
1-25 of 320 results

2021 Jeep Grand Cherokee

Mid-size SUV
Seats
5
Fuel Economy
19 - 19City MPG
26 - 26Hwy MPG
NHTSA Rating Summary
Copilot Rating
Dimensions

Why Use CoPilot?

Shop and buy your next car with confidence. CoPilot searches every car at every dealer, every day, and ranks them based on what matters to you.


When you shop for a new or used car, CoPilot helps you know more. We search every car at every dealer so you don't have to, we give you data and insights you won't find anywhere else, and we rank every car so it's easy to find the best car at the best price.


When you're ready to buy your next car, CoPilot helps you make sure you never get taken advantage of at the dealership. Would you like to know more than the salesperson? CoPilot helps you avoid any tricks, traps, and scams. Know how and what you can negotiate. With CoPilot, you'll save time, money, and frustration.

© 2024 CoPilot. All Rights Reserved.