Cars for Sale in Chicago, Illinois

Known as the Windy City, Chicago is the undisputed powerhouse city of the Midwest. It first came to prominence as the United States’s largest meatpacking center. Later, the city became a major railroad hub, which led to a boom in manufacturing, which still influences the city today. Now, Chicago has a diverse economy, home to 12 Fortune 500 companies across a myriad industries.

Chicago’s culture is noteworthy for its rich Improv comedy scene, supporting nationally-known stages such as The Second City and IO Theater. Jazz heritage is strong is strong in Chicago, which hosts one of the country’s largest festivals. The city’s residents have been instrumental in pushing various other musical genres to the forefront, including House, Industrial, Punk, and New Wave. Every year, Chicago hosts Lollapalooza and the Pitchfork Music Festival.

The massive O’Hare Airport, the highest-volume airport in the world, is based in Chicago, making the city one of the United States’s most major transportation hubs. Chicago’s Kennedy and Dan Ryan expressways are the busiest in the state. Because of its industrial heritage, many Chicagoans prefer American models to imports, though both are highly popular.

Browse our cars and trucks for sale near Chicago, IL

Makes

Top 28 Listings near Chicago, IL

2016 GMC ACADIA DENALI
  20

Mileage: 64,945
Price: $29,490
Condition: Used
Color: Black
Highland, IN
InstaVIN Vehicle History and Title Reports for 2016 GMC ACADIA DENALI in Highland IN
2018 JEEP GRAND CHEROKEE
  22

Mileage: 0
Price: $43,265
Condition: New
Color: White
Union Grove, WI
InstaVIN Vehicle History and Title Reports for 2018 JEEP GRAND CHEROKEE in Union Grove WI
2010 DODGE CHALLENGER SRT8
  23

Mileage: 22,642
Price: $24,495
Price Reduced
Condition: Used
Color: Silver
Union Grove, WI
InstaVIN Vehicle History and Title Reports for 2010 DODGE CHALLENGER SRT8 in Union Grove WI
2019 JEEP CHEROKEE LATITUDE PLUS
  19

Mileage: 0
Price: $34,025
Condition: New
Color: Gray
Union Grove, WI
InstaVIN Vehicle History and Title Reports for 2019 JEEP CHEROKEE LATITUDE PLUS in Union Grove WI
2018 JEEP WRANGLER UNLIMITED SPORT
  29

Mileage: 0
Price: $39,242
Condition: New
Color: Red
Union Grove, WI
InstaVIN Vehicle History and Title Reports for 2018 JEEP WRANGLER UNLIMITED SPORT in Union Grove WI
2018 JEEP WRANGLER UNLIMITED SAHARA
  26

Mileage: 0
Price: $43,245
Condition: New
Color: Red
Union Grove, WI
InstaVIN Vehicle History and Title Reports for 2018 JEEP WRANGLER UNLIMITED SAHARA in Union Grove WI
2018 JEEP WRANGLER UNLIMITED SAHARA
  27

Mileage: 0
Price: $48,326
Condition: New
Color: White
Union Grove, WI
InstaVIN Vehicle History and Title Reports for 2018 JEEP WRANGLER UNLIMITED SAHARA in Union Grove WI
2003 GMC ENVOY SLT
  21

Mileage: 174,804
Price: $3,495
Condition: Used
Color: Black
Union Grove, WI
InstaVIN Vehicle History and Title Reports for 2003 GMC ENVOY SLT in Union Grove WI
2019 JEEP CHEROKEE LATITUDE PLUS
  19

Mileage: 0
Price: $32,461
Condition: New
Color: Silver
Union Grove, WI
InstaVIN Vehicle History and Title Reports for 2019 JEEP CHEROKEE LATITUDE PLUS in Union Grove WI
2018 JEEP RENEGADE
  22

Mileage: 0
Price: $32,063
Condition: New
Color: Gray
Union Grove, WI
InstaVIN Vehicle History and Title Reports for 2018 JEEP RENEGADE in Union Grove WI
2019 JEEP CHEROKEE LATITUDE PLUS
  22

Mileage: 0
Price: $32,087
Condition: New
Color: Black
Union Grove, WI
InstaVIN Vehicle History and Title Reports for 2019 JEEP CHEROKEE LATITUDE PLUS in Union Grove WI
2019 JEEP CHEROKEE LATITUDE PLUS
  17

Mileage: 8
Price: $30,785
Condition: New
Color: Gray
Union Grove, WI
InstaVIN Vehicle History and Title Reports for 2019 JEEP CHEROKEE LATITUDE PLUS in Union Grove WI
2016 CHEVROLET CRUZE LT
  19

Mileage: 31,451
Price: $14,995
Condition: Used
Color: Blue
Highland, IN
InstaVIN Vehicle History and Title Reports for 2016 CHEVROLET CRUZE LT in Highland IN
2014 CHEVROLET EQUINOX LT LT1
  20

Mileage: 91,440
Price: $12,993
Condition: Used
Color: Silver
Highland, IN
InstaVIN Vehicle History and Title Reports for 2014 CHEVROLET EQUINOX LT LT1 in Highland IN
2010 FORD EXPLORER SPORT TRAC XLT
  22

Mileage: 72,612
New Listing
Price: $16,995
Condition: Used
Color: Blue
Highland, IN
InstaVIN Vehicle History and Title Reports for 2010 FORD EXPLORER SPORT TRAC XLT in Highland IN
2015 JEEP CHEROKEE LIMITED EDITION
  20

Mileage: 21,377
Price: $22,997
Condition: Used
Color: Black
Highland, IN
InstaVIN Vehicle History and Title Reports for 2015 JEEP CHEROKEE LIMITED EDITION in Highland IN
2015 CHEVROLET EQUINOX LT LT1
  20

Mileage: 39,131
Price: $16,995
Condition: Used
Color: Gray
Highland, IN
InstaVIN Vehicle History and Title Reports for 2015 CHEVROLET EQUINOX LT LT1 in Highland IN
2015 CHEVROLET EQUINOX LTZ
  20

Mileage: 38,972
Price: $21,945
Condition: Used
Color: Black
Highland, IN
InstaVIN Vehicle History and Title Reports for 2015 CHEVROLET EQUINOX LTZ in Highland IN
2014 CHEVROLET EQUINOX LT LT1
  20

Mileage: 83,935
Price: $14,995
Condition: Used
Color: Red
Highland, IN
InstaVIN Vehicle History and Title Reports for 2014 CHEVROLET EQUINOX LT LT1 in Highland IN
2018 CHEVROLET SILVERADO 1500 LT LT1
  20

Mileage: 17,573
Price: $31,994
Condition: Used
Color: Red
Highland, IN
InstaVIN Vehicle History and Title Reports for 2018 CHEVROLET SILVERADO 1500 LT LT1 in Highland IN
2015 CADILLAC ATS LUXURY
  20

Mileage: 10,916
Price: $23,494
Condition: Used
Color: Black
Highland, IN
InstaVIN Vehicle History and Title Reports for 2015 CADILLAC ATS LUXURY in Highland IN
2001 MERCURY GRAND MARQUIS LS
  20

Mileage: 115,776
Price: $4,800
Condition: Used
Color: Gray
Highland, IN
InstaVIN Vehicle History and Title Reports for 2001 MERCURY GRAND MARQUIS LS in Highland IN
2015 CHEVROLET SILVERADO 1500 WORK TRUCK
  20

Mileage: 27,842
Price: $27,699
Condition: Used
Color: Blue
Highland, IN
InstaVIN Vehicle History and Title Reports for 2015 CHEVROLET SILVERADO 1500 WORK TRUCK in Highland IN
2017 GMC SIERRA 1500
  17

Mileage: 14,905
Price: $21,054
Condition: Used
Color: White
Highland, IN
InstaVIN Vehicle History and Title Reports for 2017 GMC SIERRA 1500 in Highland IN
2015 FORD FUSION SE
  20

Mileage: 30,261
Price: $14,066
Price Reduced
Condition: Used
Color: White
Highland, IN
InstaVIN Vehicle History and Title Reports for 2015 FORD FUSION SE in Highland IN
2015 CHEVROLET EQUINOX LT LT1
  20

Mileage: 30,325
Price: $22,290
Condition: Used
Color: Gray
Highland, IN
InstaVIN Vehicle History and Title Reports for 2015 CHEVROLET EQUINOX LT LT1 in Highland IN
2014 BUICK ENCLAVE LEATHER GROUP
  20

Mileage: 70,381
Price: $19,994
Price Reduced
Condition: Used
Color: Red
Highland, IN
InstaVIN Vehicle History and Title Reports for 2014 BUICK ENCLAVE LEATHER GROUP in Highland IN
2018 CHEVROLET MALIBU LT LT1
  20

Mileage: 33,284
Price: $18,995
Condition: Used
Color: Silver
Highland, IN
InstaVIN Vehicle History and Title Reports for 2018 CHEVROLET MALIBU LT LT1 in Highland IN

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