Windy City Motors in Chicago, IL
Dealer Analysis 11 Deals Found
485 Cars for sale now, starting at $4,250
Avg. Price: 19723.2
Typical Price Range: 11850.0–28995.0
Average Savings ($) Below Market Price
Avg. Savings: $2,138
Save up to $4,930 below est. market price
% of Used Cars That Are Deals
Avg. Mileage: 105793.0
Typical Mileage Range: 47830.6–163791.0
% of Listings with Valid Price, Mileage, and Photo
- This Dealer
- Average Dealer
Windy City Motors is given a 3.4 "overall dealer rating" based on our analysis of 344 cars the dealer recently listed for sale. This assesses the dealer's price competitiveness, responsiveness to inquiries, and information transparency (how good the dealers are at providing basic information such as vehicle photos, price and mileage).
Inventory Analysis
Vehicle Age
Top Makes
Top Bodystyles
Domestic/Foreign
Luxury/Non-Luxury
Showing 1-20 of 485 Listings
Sort by:
$24,896
GREAT DEAL
2019 Lexus NX 300 F SPORT
- 39,735 Miles
- Listed 109 days ago
- Chicago, IL (0 mi away)
- $4,930 Below market value of $29,826
- iSeeCars Dealer Score
Additional info close
Used 2019 Lexus NX 300 F SPORT for Sale
39,735 Miles
Chicago, IL (0 mi away)
| Category | Used Cars |
| Price | $24,896 |
| For Sale By | dealer |
| iSeeCars Dealer Score | |
| Engine | 4-cylinder |
| Fuel Type | Gas |
| Seats | 5 Seats |
| VIN | JTJYARBZ1K2152082 |
| Location | Chicago, IL - 0 mi. |
| Features | bluetooth, child safety, navigation, backup camera, internet radio |
| Mileage | 39,735 mi. |
| Transmission | Automatic |
| Exterior Color | Red |
| Interior Color | Black |
| MPG | 25 combined |
| Drivetrain | Front-wheel drive |
$4,250
GREAT DEAL
2006 Jeep Grand Cherokee Laredo
- 168,407 Miles
- Listed 12 days ago
- Chicago, IL (0 mi away)
- $729 Below market value of $4,979
- iSeeCars Dealer Score
Additional info close
Used 2006 Jeep Grand Cherokee Laredo for Sale
168,407 Miles
Chicago, IL (0 mi away)
| Category | Used Cars |
| Price | $4,250 |
| For Sale By | dealer |
| iSeeCars Dealer Score | |
| Engine | 6-cylinder |
| Fuel Type | Gas |
| Seats | 5 Seats |
| VIN | 1J4GS48K46C148997 |
| Location | Chicago, IL - 0 mi. |
| Features | child safety, power outlet, anti-theft system |
| Mileage | 168,407 mi. |
| Transmission | Automatic |
| Exterior Color | Dark khaki pearl |
| Interior Color | Beige |
| MPG | 17 combined |
| Drivetrain | Rear-wheel drive |
$14,850
GREAT DEAL
2015 Chrysler 200 Limited
- 26,793 Miles
- Listed 299 days ago
- Chicago, IL (0 mi away)
- $4,085 Below market value of $18,935
- iSeeCars Dealer Score
Additional info close
Used 2015 Chrysler 200 Limited for Sale
26,793 Miles
Chicago, IL (0 mi away)
| Category | Used Cars |
| Price | $14,850 |
| For Sale By | dealer |
| iSeeCars Dealer Score | |
| Engine | 4-cylinder |
| Fuel Type | Gas |
| Seats | 5 Seats |
| VIN | 1C3CCCAB6FN717508 |
| Location | Chicago, IL - 0 mi. |
| Features | bluetooth, child safety, alloy wheels, satellite radio, voice recognition |
| Mileage | 26,793 mi. |
| Transmission | Automatic |
| Exterior Color | Silver |
| Interior Color | Black |
| MPG | 28 combined |
| Drivetrain | Front-wheel drive |
$17,995
GREAT DEAL
2018 Chevrolet Equinox LT
- 27,397 Miles
- Listed 299 days ago
- Chicago, IL (0 mi away)
- $2,207 Below market value of $20,202
- iSeeCars Dealer Score
Additional info close
Used 2018 Chevrolet Equinox LT for Sale
27,397 Miles
Chicago, IL (0 mi away)
| Category | Used Cars |
| Price | $17,995 |
| For Sale By | dealer |
| iSeeCars Dealer Score | |
| Engine | 4-cylinder |
| Fuel Type | Gas |
| Seats | 5 Seats |
| VIN | 2GNAXTEX7J6303784 |
| Location | Chicago, IL - 0 mi. |
| Features | bluetooth, child safety, backup camera, internet radio, alloy wheels |
| Mileage | 27,397 mi. |
| Transmission | Automatic |
| Exterior Color | White |
| Interior Color | Black |
| MPG | 24 combined |
| Drivetrain | 4X4 |
$29,896
GREAT DEAL
2020 Toyota Sienna LE
- 74,841 Miles
- Listed 22 days ago
- Chicago, IL (0 mi away)
- $3,394 Below market value of $33,290
- iSeeCars Dealer Score
Additional info close
Used 2020 Toyota Sienna LE for Sale
74,841 Miles
Chicago, IL (0 mi away)
| Category | Used Cars |
| Price | $29,896 |
| For Sale By | dealer |
| iSeeCars Dealer Score | |
| Engine | 6-cylinder |
| Fuel Type | Gas |
| Seats | 0 Seats |
| VIN | 5TDKZ3DC3LS064281 |
| Location | Chicago, IL - 0 mi. |
| Features | bluetooth, captain's chair, child safety, navigation, backup camera |
| Mileage | 74,841 mi. |
| Transmission | Automatic |
| Exterior Color | Gray |
| Interior Color | Gray |
| MPG | 21 combined |
| Drivetrain | Front-wheel drive |
$14,896
$16,995
GOOD DEAL
2017 Jeep Grand Cherokee Limited
- 115,693 Miles
- Listed 39 days ago
- Chicago, IL (0 mi away)
- $393 Below market value of $15,289
- iSeeCars Dealer Score
Additional info close
Used 2017 Jeep Grand Cherokee Limited for Sale
115,693 Miles
Chicago, IL (0 mi away)
| Category | Used Cars |
| Price | $14,896 |
| For Sale By | dealer |
| iSeeCars Dealer Score | |
| Engine | 6-cylinder |
| Fuel Type | Gas |
| Seats | 5 Seats |
| VIN | 1C4RJFBG3HC932981 |
| Location | Chicago, IL - 0 mi. |
| Features | bluetooth, child safety, backup camera, leather upholstery, alloy wheels |
| Mileage | 115,693 mi. |
| Transmission | Automatic |
| Exterior Color | White |
| Interior Color | Black |
| MPG | 21 combined |
| Drivetrain | 4X4 |
$43,896
$44,896
GOOD DEAL
2022 Chevrolet Tahoe High Country
- 103,417 Miles
- Listed 54 days ago
- Chicago, IL (0 mi away)
- $2,392 Below market value of $46,288
- iSeeCars Dealer Score
Additional info close
Used 2022 Chevrolet Tahoe High Country for Sale
103,417 Miles
Chicago, IL (0 mi away)
| Category | Used Cars |
| Price | $43,896 |
| For Sale By | dealer |
| iSeeCars Dealer Score | |
| Engine | 8-cylinder |
| Fuel Type | Gas |
| Seats | 7 Seats |
| VIN | 1GNSKTKL3NR364953 |
| Location | Chicago, IL - 0 mi. |
| Features | bluetooth, child safety, navigation, backup camera, leather upholstery |
| Mileage | 103,417 mi. |
| Transmission | Automatic |
| Exterior Color | White |
| Interior Color | Brown |
| MPG | 16 combined |
| Drivetrain | 4X4 |
$29,896
GOOD DEAL
2005 Bentley Continental GT Turbo
- 57,656 Miles
- Listed 271 days ago
- Chicago, IL (0 mi away)
- $2,075 Below market value of $31,971
- iSeeCars Dealer Score
Additional info close
Used 2005 Bentley Continental GT Turbo for Sale
57,656 Miles
Chicago, IL (0 mi away)
| Category | Used Cars |
| Price | $29,896 |
| For Sale By | dealer |
| iSeeCars Dealer Score | |
| Engine | 12-cylinder |
| Fuel Type | Gas |
| Seats | 4 Seats |
| VIN | SCBCR63W25C026520 |
| Location | Chicago, IL - 0 mi. |
| Features | navigation, leather upholstery, alloy wheels |
| Mileage | 57,656 mi. |
| Transmission | Automatic |
| Exterior Color | Moonbeam silver |
| Interior Color | Gray |
| MPG | 12 combined |
| Drivetrain | All-wheel drive |
$21,850
GOOD DEAL
2019 Ram Ram Pickup 1500 Big Horn
- 118,241 Miles
- Listed 235 days ago
- Chicago, IL (0 mi away)
- $1,468 Below market value of $23,318
- iSeeCars Dealer Score
Additional info close
Used 2019 Ram Ram Pickup 1500 Big Horn for Sale
118,241 Miles
Chicago, IL (0 mi away)
| Category | Used Cars |
| Price | $21,850 |
| For Sale By | dealer |
| iSeeCars Dealer Score | |
| Engine | 6-cylinder |
| Fuel Type | Gas |
| Seats | 6 Seats |
| VIN | 1C6RRFFG7KN920080 |
| Location | Chicago, IL - 0 mi. |
| Features | bluetooth, child safety, backup camera, alloy wheels, voice recognition |
| Mileage | 118,241 mi. |
| Transmission | Automatic |
| Exterior Color | White |
| Interior Color | Black |
| MPG | 21 combined |
| Drivetrain | 4X4 |
$15,850
$16,995
GOOD DEAL
2016 Chevrolet Express 3500
- 133,461 Miles
- Listed 318 days ago
- Chicago, IL (0 mi away)
- $1,320 Below market value of $17,170
- iSeeCars Dealer Score
Additional info close
Used 2016 Chevrolet Express 3500 for Sale
133,461 Miles
Chicago, IL (0 mi away)
| Category | Used Cars |
| Price | $15,850 |
| For Sale By | dealer |
| iSeeCars Dealer Score | |
| Engine | 8-cylinder |
| Fuel Type | Gas |
| Seats | 2 Seats |
| VIN | 1GB0GRFF6G1239508 |
| Location | Chicago, IL - 0 mi. |
| Mileage | 133,461 mi. |
| Transmission | Automatic |
| Exterior Color | White |
| Interior Color | Gray |
| Drivetrain | Rear-wheel drive |
$13,995
GOOD DEAL
2010 Toyota Sequoia Platinum
- 184,777 Miles
- Listed 327 days ago
- Chicago, IL (0 mi away)
- $528 Below market value of $14,523
- iSeeCars Dealer Score
Additional info close
Used 2010 Toyota Sequoia Platinum for Sale
184,777 Miles
Chicago, IL (0 mi away)
| Category | Used Cars |
| Price | $13,995 |
| For Sale By | dealer |
| iSeeCars Dealer Score | |
| Engine | 8-cylinder |
| Fuel Type | Flex fuel |
| Seats | 7 Seats |
| VIN | 5TDDW5G18AS024234 |
| Location | Chicago, IL - 0 mi. |
| Features | child safety, navigation, backup camera, leather upholstery, sunroof |
| Mileage | 184,777 mi. |
| Transmission | Automatic |
| Exterior Color | Nautical blue metallic |
| Interior Color | Gray |
| MPG | 10 combined |
| Drivetrain | 4X4 |
$37,896
FAIR DEAL
2021 Toyota Tacoma TRD Off-Road
- 43,607 Miles
- Listed 3 days ago
- Chicago, IL (0 mi away)
- $945 Above market value of $36,951
- iSeeCars Dealer Score
Additional info close
Used 2021 Toyota Tacoma TRD Off-Road for Sale
43,607 Miles
Chicago, IL (0 mi away)
| Category | Used Cars |
| Price | $37,896 |
| For Sale By | dealer |
| iSeeCars Dealer Score | |
| Engine | 6-cylinder |
| Fuel Type | Gas |
| Seats | 5 Seats |
| VIN | 5TFCZ5AN8MX263327 |
| Location | Chicago, IL - 0 mi. |
| Features | bluetooth, child safety, backup camera, alloy wheels, satellite radio |
| Mileage | 43,607 mi. |
| Transmission | Automatic |
| Exterior Color | White |
| Interior Color | Black |
| MPG | 20 combined |
| Drivetrain | 4X4 |
$26,896
$28,995
FAIR DEAL
2018 Ram Ram Pickup 1500 Night
- 88,128 Miles
- Listed 60 days ago
- Chicago, IL (0 mi away)
- $103 Above market value of $26,999
- iSeeCars Dealer Score
Additional info close
Used 2018 Ram Ram Pickup 1500 Night for Sale
88,128 Miles
Chicago, IL (0 mi away)
| Category | Used Cars |
| Price | $26,896 |
| For Sale By | dealer |
| iSeeCars Dealer Score | |
| Engine | 8-cylinder |
| Fuel Type | Gas |
| Seats | 5 Seats |
| VIN | 1C6RR7MT4JS259808 |
| Location | Chicago, IL - 0 mi. |
| Features | bluetooth, child safety, backup camera, alloy wheels, satellite radio |
| Mileage | 88,128 mi. |
| Transmission | Automatic |
| Exterior Color | White |
| Interior Color | Black |
| MPG | 17 combined |
| Drivetrain | 4X4 |
$43,995
$44,995
FAIR DEAL
2023 Acura MDX SH-AWD w/Advance
- 41,434 Miles
- Listed 73 days ago
- Chicago, IL (0 mi away)
- $465 Above market value of $44,460
- iSeeCars Dealer Score
Additional info close
Used 2023 Acura MDX SH-AWD w/Advance for Sale
41,434 Miles
Chicago, IL (0 mi away)
| Category | Used Cars |
| Price | $43,995 |
| For Sale By | dealer |
| iSeeCars Dealer Score | |
| Engine | 6-cylinder |
| Fuel Type | Gas |
| Seats | 7 Seats |
| VIN | 5J8YE1H81PL020109 |
| Location | Chicago, IL - 0 mi. |
| Features | bluetooth, child safety, navigation, backup camera, leather upholstery |
| Mileage | 41,434 mi. |
| Transmission | Automatic |
| Exterior Color | White |
| Interior Color | Brown |
| MPG | 21 combined |
| Drivetrain | All-wheel drive |
$15,896
$17,995
FAIR DEAL
2017 GMC Acadia SLT-1
- 112,226 Miles
- Listed 38 days ago
- Chicago, IL (0 mi away)
- $382 Above market value of $15,514
- iSeeCars Dealer Score
Additional info close
Used 2017 GMC Acadia SLT-1 for Sale
112,226 Miles
Chicago, IL (0 mi away)
| Category | Used Cars |
| Price | $15,896 |
| For Sale By | dealer |
| iSeeCars Dealer Score | |
| Engine | 6-cylinder |
| Fuel Type | Gas |
| Seats | 6 Seats |
| VIN | 1GKKNULS9HZ291978 |
| Location | Chicago, IL - 0 mi. |
| Features | bluetooth, captain's chair, child safety, backup camera, leather upholstery |
| Mileage | 112,226 mi. |
| Transmission | Automatic |
| Exterior Color | Gray |
| Interior Color | Gray |
| MPG | 20 combined |
| Drivetrain | 4X4 |
$28,995
FAIR DEAL
2019 Jeep Wrangler Unlimited Rubicon
- 106,958 Miles
- Listed 33 days ago
- Chicago, IL (0 mi away)
- $247 Above market value of $28,748
- iSeeCars Dealer Score
Additional info close
Used 2019 Jeep Wrangler Unlimited Rubicon for Sale
106,958 Miles
Chicago, IL (0 mi away)
| Category | Used Cars |
| Price | $28,995 |
| For Sale By | dealer |
| iSeeCars Dealer Score | |
| Engine | 4-cylinder |
| Fuel Type | Gas |
| Seats | 5 Seats |
| VIN | 1C4HJXFN7KW538531 |
| Location | Chicago, IL - 0 mi. |
| Features | bluetooth, child safety, backup camera, alloy wheels, satellite radio |
| Mileage | 106,958 mi. |
| Transmission | Automatic |
| Exterior Color | White |
| Interior Color | Black |
| MPG | 22 combined |
| Drivetrain | 4X4 |
$15,896
$17,995
FAIR DEAL
2019 Chevrolet Colorado Work Truck
- 87,650 Miles
- Listed 27 days ago
- Chicago, IL (0 mi away)
- $404 Above market value of $15,491
- iSeeCars Dealer Score
Additional info close
Used 2019 Chevrolet Colorado Work Truck for Sale
87,650 Miles
Chicago, IL (0 mi away)
| Category | Used Cars |
| Price | $15,896 |
| For Sale By | dealer |
| iSeeCars Dealer Score | |
| Engine | 4-cylinder |
| Fuel Type | Gas |
| Seats | 4 Seats |
| VIN | 1GCHSBEA0K1227356 |
| Location | Chicago, IL - 0 mi. |
| Features | bluetooth, backup camera, voice recognition, power outlet, anti-theft system |
| Mileage | 87,650 mi. |
| Transmission | Automatic |
| Exterior Color | Blue |
| Interior Color | Gray |
| Drivetrain | 4X2 |
$20,896
$22,896
GOOD DEAL
2020 Jeep Grand Cherokee Trailhawk
- 103,910 Miles
- Listed 82 days ago
- Chicago, IL (0 mi away)
- $442 Below market value of $21,338
- iSeeCars Dealer Score
Additional info close
Used 2020 Jeep Grand Cherokee Trailhawk for Sale
103,910 Miles
Chicago, IL (0 mi away)
| Category | Used Cars |
| Price | $20,896 |
| For Sale By | dealer |
| iSeeCars Dealer Score | |
| Engine | 6-cylinder |
| Fuel Type | Gas |
| Seats | 5 Seats |
| VIN | 1C4RJFLG3LC288924 |
| Location | Chicago, IL - 0 mi. |
| Features | bluetooth, child safety, navigation, backup camera, leather upholstery |
| Mileage | 103,910 mi. |
| Transmission | Automatic |
| Exterior Color | White |
| Interior Color | Black |
| MPG | 21 combined |
| Drivetrain | 4X4 |
$16,995
FAIR DEAL
2005 HUMMER H2 Base
- 120,871 Miles
- Listed 87 days ago
- Chicago, IL (0 mi away)
- $326 Above market value of $16,668
- iSeeCars Dealer Score
Additional info close
Used 2005 HUMMER H2 Base for Sale
120,871 Miles
Chicago, IL (0 mi away)
| Category | Used Cars |
| Price | $16,995 |
| For Sale By | dealer |
| iSeeCars Dealer Score | |
| Engine | 8-cylinder |
| Fuel Type | Gas |
| Seats | 5 Seats |
| VIN | 5GRGN23U25H121940 |
| Location | Chicago, IL - 0 mi. |
| Features | leather upholstery, alloy wheels, anti-theft system |
| Mileage | 120,871 mi. |
| Transmission | Automatic |
| Exterior Color | Black |
| Interior Color | Black |
| Drivetrain | Four-wheel drive |
$26,896
$27,896
FAIR DEAL
2021 Jeep Grand Cherokee 80th Edition
- 48,631 Miles
- Listed 151 days ago
- Chicago, IL (0 mi away)
- $500 Above market value of $27,396
- iSeeCars Dealer Score
Additional info close
Used 2021 Jeep Grand Cherokee 80th Edition for Sale
48,631 Miles
Chicago, IL (0 mi away)
| Category | Used Cars |
| Price | $26,896 |
| For Sale By | dealer |
| iSeeCars Dealer Score | |
| Engine | 6-cylinder |
| Fuel Type | Gas |
| Seats | 5 Seats |
| VIN | 1C4RJEBG9MC835529 |
| Location | Chicago, IL - 0 mi. |
| Features | bluetooth, child safety, navigation, backup camera, leather upholstery |
| Mileage | 48,631 mi. |
| Transmission | Automatic |
| Exterior Color | Burgundy |
| Interior Color | Black |
| MPG | 21 combined |
| Drivetrain | 4X2 |
Page 1 of 25
Other Nearby Dealers
Used Cars for Sale Insights
Find More Cars For Sale
Explore Models
Ford F-150
Save $26,402 on 15,992 Deals
103,206 Listings from $1,250
103,206 Listings from $1,250
Chevrolet Cruze
Save $3,950 on 1,087 Deals
3,102 Listings from $1,350
3,102 Listings from $1,350
Honda CR-V
Save $7,254 on 6,168 Deals
30,922 Listings from $1,450
30,922 Listings from $1,450
Hyundai Elantra
Save $5,026 on 3,030 Deals
24,960 Listings from $1,925
24,960 Listings from $1,925
Volkswagen Jetta
Save $5,112 on 2,245 Deals
12,338 Listings from $1,500
12,338 Listings from $1,500
Dodge Charger
Save $14,165 on 2,826 Deals
8,419 Listings from $2,400
8,419 Listings from $2,400
Kia Sorento
Save $7,303 on 3,299 Deals
20,351 Listings from $1,800
20,351 Listings from $1,800
Mazda Mazda3
Save $5,537 on 1,181 Deals
6,025 Listings from $1,500
6,025 Listings from $1,500
Subaru Forester
Save $7,743 on 4,237 Deals
20,525 Listings from $1,600
20,525 Listings from $1,600