CarGurus Logo Homepage Link
  • Buy
    • Used cars
    • New cars
    • Certified pre-owned
    • Start your purchase online
    • Dealerships near me
  • Sell
    • Sell my car
    • Sell my car FAQs
  • Finance
    • Prequalify for financing
    • How does it work?
    • Financing FAQs
  • Research
    • Test drive reviews
    • Price trends
    • Tips & advice
    • Electric cars
    • Compare cars
  • Discover
    The latest way to shop:
    smarter research, better
    listings.
  • Saved cars & searches
  • Sign in / Register
    • My account
    • Saved searches
    • Saved cars
    • Recommended cars
    • Browsing history
    • Financing dashboard
      • United States (EN)
      • Estados Unidos (ES)
      • Canada (EN)
      • Canada (FR)
      • United Kingdom

Certified Toyota Highlander for Sale near Chicago, IL

26 results
Chicago, IL
2021 Toyota Highlander LE AWD Zeigler Ford of North Riverside

2021 Toyota Highlander

LE AWD

54,548 miles

$26,484

Great Deal
Certified Pre-Owned
Riverside, IL
9 mi away
Year:
2021
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
295 hp 3.5L V6
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Transmission:
8-Speed Automatic
Mileage:
54,548
Stock number:
5754A
VIN:
5TDBZRBH9MS546675

Sponsored

2024 Toyota Highlander XLE AWD

2024 Toyota Highlander

XLE AWD

40,321 miles

$39,987

Fair Deal
Certified Pre-Owned
Hodgkins, IL
15 mi away
Year:
2024
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
Midnight Black Metallic
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
40,321
Stock number:
P11885
VIN:
5TDKDRBH8RS559374

Sponsored

2023 Toyota Highlander XLE FWD

2023 Toyota Highlander

XLE FWD

73,150 miles

$29,600

Great Deal
Certified Pre-Owned
Matteson, IL
27 mi away
Year:
2023
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Front-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
Celestial Silver Metallic
Combined gas mileage:
25 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
73,150
Stock number:
P524681
VIN:
5TDKDRAH9PS524681

Sponsored

2021 Toyota Highlander LE AWD

2021 Toyota Highlander

LE AWD

54,548 miles

$26,484

Great Deal
Certified Pre-Owned
Riverside, IL
9 mi away
Year:
2021
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
295 hp 3.5L V6
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Transmission:
8-Speed Automatic
Mileage:
54,548
Stock number:
5754A
VIN:
5TDBZRBH9MS546675

2022 Toyota Highlander XLE AWD

2022 Toyota Highlander

XLE AWD

28,110 miles

$35,995

Fair Deal
Certified Pre-Owned
Frankfort, IL
28 mi away
Year:
2022
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
295 hp 3.5L V6
Exterior color:
Opulent Amber
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
28,110
Stock number:
48525
VIN:
5TDGZRBH0NS225079

2023 Toyota Highlander LE AWD

2023 Toyota Highlander

LE AWD

19,043 miles

$32,847

Great Deal
Certified Pre-Owned
Merrillville, IN
33 mi away
Year:
2023
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
Silver
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Gray
Transmission:
Automatic
Mileage:
19,043
Stock number:
B0G505125
VIN:
5TDKDRBH7PS505125

Preparing for a close up...

Photos coming soon

2023 Toyota Highlander

XLE FWD

73,150 miles

$29,600

Great Deal
Certified Pre-Owned
Matteson, IL
27 mi away
Year:
2023
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Front-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
Celestial Silver Metallic
Combined gas mileage:
25 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
73,150
Stock number:
P524681
VIN:
5TDKDRAH9PS524681

Preparing for a close up...

Photos coming soon

2022 Toyota Highlander

XSE AWD

45,990 miles

$37,411

Fair Deal
Certified Pre-Owned
Schaumburg, IL
27 mi away
Year:
2022
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
295 hp 3.5L V6
Exterior color:
White
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Black Ea20
Transmission:
Automatic
Mileage:
45,990
Stock number:
260221A
VIN:
5TDJZRBH3NS195453

Preparing for a close up...

Photos coming soon

2022 Toyota Highlander

XLE AWD

36,200 miles

$36,685

Fair Deal
Certified Pre-Owned
Niles, IL
16 mi away
Year:
2022
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
295 hp 3.5L V6
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Gray
Transmission:
Automatic
Mileage:
36,200
Stock number:
X15316
VIN:
5TDGZRBH1NS164597

Preparing for a close up...

Photos coming soon

2022 Toyota Highlander

XSE AWD

92,904 miles

$29,998

Good Deal
Certified Pre-Owned
Hodgkins, IL
15 mi away
Year:
2022
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
295 hp 3.5L V6
Exterior color:
Magnetic Gray Metallic
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Cockpit Red
Transmission:
Automatic
Mileage:
92,904
Stock number:
P11696A
VIN:
5TDJZRBH3NS178717

Preparing for a close up...

Photos coming soon

2021 Toyota Highlander

XLE AWD

43,415 miles

$33,093

Fair Deal
Certified Pre-Owned
Calumet City, IL
19 mi away
Year:
2021
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
295 hp 3.5L V6
Exterior color:
Midnight Black Metallic
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
43,415
Stock number:
7105A
VIN:
5TDHZRBH4MS102162

Preparing for a close up...

Photos coming soon

2025 Toyota Highlander

XSE AWD

18,853 miles

$44,473

Fair Deal
Certified Pre-Owned
Calumet City, IL
19 mi away
Year:
2025
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
Midnight Black Metallic
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
18,853
Stock number:
P7065
VIN:
5TDKDRBH4SS575996

Preparing for a close up...

Photos coming soon

2021 Toyota Highlander

Limited AWD

26,781 miles

$32,995

Great Deal
Certified Pre-Owned
Alsip, IL
16 mi away
Year:
2021
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
295 hp 3.5L V6
Exterior color:
Not Specified
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Transmission:
8-Speed Automatic
Mileage:
26,781
Stock number:
1054
VIN:
5TDDZRBH1MS098330

Preparing for a close up...

Photos coming soon

2023 Toyota Highlander

LE FWD

46,854 miles

$29,990

Good Deal
Certified Pre-Owned
Kenosha, WI
50 mi away
Year:
2023
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Front-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
Magnetic Gray Metallic
Combined gas mileage:
25 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
46,854
Stock number:
T260445A
VIN:
5TDKDRAH2PS511285

Preparing for a close up...

Photos coming soon

2023 Toyota Highlander

LE FWD

68,636 miles

$28,472

Fair Deal
Certified Pre-Owned
Bolingbrook, IL
27 mi away
Year:
2023
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Front-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
White
Combined gas mileage:
25 MPG
Fuel type:
Gasoline
Interior color:
Gray (Graphite)
Transmission:
8-Speed Automatic
Mileage:
68,636
Stock number:
P15775
VIN:
5TDKDRAH5PS018927

Preparing for a close up...

Photos coming soon

2021 Toyota Highlander

XLE AWD

49,941 miles

$31,999

Fair Deal
Certified Pre-Owned
Tinley Park, IL
22 mi away
Year:
2021
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
295 hp 3.5L V6
Exterior color:
Gray
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Gray (Graphite)
Transmission:
8-Speed Automatic
Mileage:
49,941
Stock number:
463321
VIN:
5TDGZRBH9MS150266

Preparing for a close up...

Photos coming soon

2023 Toyota Highlander

XLE AWD

42,090 miles

$36,244

Good Deal
Certified Pre-Owned
Chicago, IL
7 mi away
Year:
2023
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
Midnight Black Metallic
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
42,090
Stock number:
69E11039
VIN:
5TDKDRBH4PS025141

Preparing for a close up...

Photos coming soon

2022 Toyota Highlander

Platinum AWD

74,510 miles

$36,999

Fair Deal
Certified Pre-Owned
Palatine, IL
27 mi away
Year:
2022
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
295 hp 3.5L V6
Exterior color:
White (Wind Chill Pearl)
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Glazed Caramel
Transmission:
Automatic
Mileage:
74,510
Stock number:
64696A
VIN:
5TDFZRBH2NS173417

Preparing for a close up...

Photos coming soon

2024 Toyota Highlander

XLE AWD

40,321 miles

$39,987

Fair Deal
Certified Pre-Owned
Hodgkins, IL
15 mi away
Year:
2024
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
Midnight Black Metallic
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
40,321
Stock number:
P11885
VIN:
5TDKDRBH8RS559374

Preparing for a close up...

Photos coming soon

2021 Toyota Highlander

Platinum AWD

75,312 miles

$33,886

Good Deal
Certified Pre-Owned
Palatine, IL
27 mi away
Year:
2021
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
295 hp 3.5L V6
Exterior color:
Magnetic Gray Metallic
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Gray (Graphite)
Transmission:
Automatic
Mileage:
75,312
Stock number:
64444A
VIN:
5TDFZRBH9MS151221

Preparing for a close up...

Photos coming soon

2024 Toyota Highlander

XLE AWD

12,906 miles

Negotiable

No Price Analysis
Certified Pre-Owned
Elmhurst, IL
17 mi away
Year:
2024
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
CELESTIAL SILVER
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Transmission:
8-Speed Automatic
Mileage:
12,906
Stock number:
TR42106
VIN:
5TDKDRBH0RS574953

Preparing for a close up...

Photos coming soon

2022 Toyota Highlander

LE FWD

59,488 miles

$29,245

No Price Analysis
Certified Pre-Owned
Schaumburg, IL
27 mi away
Year:
2022
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Front-Wheel Drive
Engine:
295 hp 3.5L V6
Exterior color:
White
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Gray (Graphite)
Transmission:
Automatic
Mileage:
59,488
Stock number:
250311A
VIN:
5TDZZRAH8NS134359

Preparing for a close up...

Photos coming soon

2022 Toyota Highlander

Platinum AWD

36,481 miles

$42,987

High Price
Certified Pre-Owned
Schaumburg, IL
27 mi away
Year:
2022
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
295 hp 3.5L V6
Exterior color:
Blue
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Black La20
Transmission:
Automatic
Mileage:
36,481
Stock number:
260386A
VIN:
5TDFZRBH1NS185882

Preparing for a close up...

Photos coming soon

2025 Toyota Highlander

XSE AWD

18,853 miles

$44,473

Fair Deal
Certified Pre-Owned
Calumet City, IL
19 mi away
Year:
2025
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
Midnight Black Metallic
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
18,853
Stock number:
P7065
VIN:
5TDKDRBH4SS575996

Sponsored

  1. Home
  2. / Certified Pre-Owned
  3. / Toyota Highlander
  4. / Illinois
  5. / Chicago

  • Toyota Highlander in Palatine IL

  • Toyota Highlander in Aurora IL

  • Toyota Highlander in Kenosha WI

  • Toyota Highlander in South Bend IN

  • Toyota Highlander in Rockford IL

  • Toyota Highlander in Milwaukee WI

  • Toyota Highlander in Janesville WI

  • Toyota Highlander in Holland MI

  • Toyota Highlander in Kalamazoo MI

  • All Used Cars

  • Manual Transmission Cars

  • Luxury Cars

  • Cars with Red Interior

  • Cheap Manual Cars

  • Hybrid Cars

  • Sports Cars

  • Electric SUVs

  • Cheap Trucks

  • Small Cars

  • Third Row SUVs

  • Three Quarter Ton Trucks

  • Lifted Trucks

  • Manual Transmission Trucks

  • Diesel Trucks

  • Hybrid SUVs

  • Dually Trucks

  • One Ton Trucks

  • Cheap SUVs

  • Lifted Ford Trucks

  • 4x4 Trucks

  • Work Trucks

  • AWD SUVs

  • Ford Trucks

  • Chevrolet Trucks

  • Toyota Trucks

  • Trucks Under $10,000

  • Cars Under $15,000

  • Sports Cars Under $20,000

  • Trucks Under $20,000

  • Used Sedans for Sale with Low Mileage

  • Used SUVs / Crossovers for Sale with Low Mileage

  • Used Hatchbacks for Sale with Low Mileage

  • Used Convertibles for Sale with Low Mileage

  • Used Vans for Sale with Low Mileage

  • Used Minivans for Sale with Low Mileage

  • Used Pickup Trucks for Sale with Low Mileage

  • Used Coupes for Sale with Low Mileage

  • Used Wagons for Sale with Low Mileage

Connect with us
Download our app
Download on the App Store Get it on Google Play
  • Company
  • About CarGurus
  • Our team
  • Press
  • Investor relations
  • Price trends
  • Careers
  • Advertise with CarGurus
  • For dealers
  • Dealer signup
  • Dealer resources
  • Terms
  • Terms of use
  • Privacy policy
  • Interest-based ads
  • Security
  • Help
  • Help center
  • Contact us
Click for the BBB Business Review of this Auto Listing Service in Cambridge MA
    • United States (EN)
    • Estados Unidos (ES)
    • Canada (EN)
    • Canada (FR)
    • United Kingdom

© 2025 CarGurus, Inc., All Rights Reserved.