CarGurus Logo Homepage Link
  • Buy
    • Used cars
    • New cars
    • Certified pre-owned
    • Start your purchase online
    • Dealerships near me
  • Sell
    • Sell my car
    • Car values
    • 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

Used Toyota Grand Highlander for Sale near Chicago, IL

83 results
Chicago, IL
2025 Toyota Grand Highlander XLE AWD Jidd Motors Mitsubishi

2025 Toyota Grand Highlander

XLE AWD

18,291 miles

$42,595

Good Deal
Des Plaines, IL
18 mi away
Year:
2025
Make:
Toyota
Model:
Grand Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
Black
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
18,291
Stock number:
JU18194
VIN:
5TDAAAB5XSS079337

Sponsored

2024 Toyota Grand Highlander XLE AWD

2024 Toyota Grand Highlander

XLE AWD

25,845 miles

$41,998

Fair Deal
Elmhurst, IL
17 mi away
Year:
2024
Make:
Toyota
Model:
Grand Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
Blueprint
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Mileage:
25,845
Stock number:
12767PA
VIN:
5TDAAAB5XRS020928

Sponsored

2025 Toyota Grand Highlander

2025 Toyota Grand Highlander

19,861 miles

$41,594

Fair Deal
16 mi away
Year:
2025
Make:
Toyota
Model:
Grand Highlander
Engine:
265 hp 2.4L I4
Exterior color:
Blueprint
Fuel type:
Gasoline
Transmission:
8-Speed Automatic
Mileage:
19,861
Stock number:
16675045
VIN:
5TDAAAA54SS027297

Sponsored

2024 Toyota Grand Highlander XLE AWD

2024 Toyota Grand Highlander

XLE AWD

21,480 miles

$41,800

Good Deal
Oak Lawn, IL
13 mi away
Year:
2024
Make:
Toyota
Model:
Grand 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:
21,480
Stock number:
OF100374C
VIN:
5TDAAAB50RS057714

2025 Toyota Grand Highlander XLE AWD

2025 Toyota Grand Highlander

XLE AWD

23,854 miles

$41,495

Good Deal
Des Plaines, IL
18 mi away
Year:
2025
Make:
Toyota
Model:
Grand 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:
Black
Transmission:
8-Speed Automatic
Mileage:
23,854
Stock number:
JU17979
VIN:
5TDAAAB57SS078162

2025 Toyota Grand Highlander XLE AWD

2025 Toyota Grand Highlander

XLE AWD

18,291 miles

$42,595

Good Deal
Des Plaines, IL
18 mi away
Year:
2025
Make:
Toyota
Model:
Grand Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
Black
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
18,291
Stock number:
JU18194
VIN:
5TDAAAB5XSS079337

Preparing for a close up...

Photos coming soon

2024 Toyota Grand Highlander

Limited AWD

26,116 miles

$44,995

Fair Deal
Certified Pre-Owned
Chicago, IL
8 mi away
Year:
2024
Make:
Toyota
Model:
Grand Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
Storm Cloud
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
26,116
Stock number:
T26063B
VIN:
5TDAAAB50RS026186

Preparing for a close up...

Photos coming soon

2024 Toyota Grand Highlander

XLE AWD

48,188 miles

$39,779

Fair Deal
Chicago, IL
9 mi away
Year:
2024
Make:
Toyota
Model:
Grand 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:
48,188
Stock number:
H32155A
VIN:
5TDAAAB5XRS018970

Preparing for a close up...

Photos coming soon

2024 Toyota Grand Highlander

Limited AWD

43,334 miles

$44,397

Fair Deal
Store transfer to Oak Lawn, IL
674 mi away • Price includes $399 shipping Price includes $399 shipping
Year:
2024
Make:
Toyota
Model:
Grand Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
Blue
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
43,334
Stock number:
27970984
VIN:
5TDAAAB56RS003284

Preparing for a close up...

Photos coming soon

2025 Toyota Grand Highlander

XLE AWD

12,951 miles

$43,998

Fair Deal
Kenosha, WI
50 mi away
Year:
2025
Make:
Toyota
Model:
Grand Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
Celestial Silver Metallic
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
12,951
Stock number:
J3518
VIN:
5TDAAAB59SS092662

Preparing for a close up...

Photos coming soon

2024 Toyota Grand Highlander

Limited AWD

29,731 miles

$45,397

Fair Deal
Store transfer to Oak Lawn, IL
706 mi away • Price includes $399 shipping Price includes $399 shipping
Year:
2024
Make:
Toyota
Model:
Grand Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
Black
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
29,731
Stock number:
28423301
VIN:
5TDAAAB51RS014225

Preparing for a close up...

Photos coming soon

2025 Toyota Grand Highlander

XLE AWD

20,362 miles

$43,000

Fair Deal
Melrose Park, IL
12 mi away
Year:
2025
Make:
Toyota
Model:
Grand Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
Black
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
20,362
Stock number:
N14914
VIN:
5TDAAAB50SS086183

Preparing for a close up...

Photos coming soon

2025 Toyota Grand Highlander

Platinum AWD

4,027 miles

$51,684

Great Deal
Highland Park, IL
21 mi away
Year:
2025
Make:
Toyota
Model:
Grand Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
Blue
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Gray
Transmission:
Automatic
Mileage:
4,027
Stock number:
H51671A
VIN:
5TDAAAB56SS079772

Preparing for a close up...

Photos coming soon

2024 Toyota Grand Highlander

XLE AWD

40,122 miles

$40,365

Good Deal
Libertyville, IL
32 mi away
Year:
2024
Make:
Toyota
Model:
Grand Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
Storm Cloud
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Light Gray
Transmission:
8-Speed Automatic
Mileage:
40,122
Stock number:
7251191A
VIN:
5TDAAAB57RS031062

Preparing for a close up...

Photos coming soon

2024 Toyota Grand Highlander

Limited AWD

17,082 miles

$46,101

Fair Deal
Libertyville, IL
30 mi away
Year:
2024
Make:
Toyota
Model:
Grand Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
White (Wind Chill Pearl)
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
17,082
Stock number:
XBP8143
VIN:
5TDAAAB51RS061285

Preparing for a close up...

Photos coming soon

2025 Toyota Grand Highlander

XLE AWD

21,226 miles

$41,895

Good Deal
Countryside, IL
14 mi away
Year:
2025
Make:
Toyota
Model:
Grand Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
Celestial Silver Metallic
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
21,226
Stock number:
CU7379
VIN:
5TDAAAB53SS078370

Preparing for a close up...

Photos coming soon

2025 Toyota Grand Highlander

XLE AWD

13,859 miles

$43,685

Fair Deal
Des Plaines, IL
18 mi away
Year:
2025
Make:
Toyota
Model:
Grand Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
Black
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
13,859
Stock number:
JU17981
VIN:
5TDAAAB51SS078156

Preparing for a close up...

Photos coming soon

2025 Toyota Grand Highlander

LE AWD

26,451 miles

$40,697

Great Deal
Store transfer to Oak Lawn, IL
833 mi away • Price includes $699 shipping Price includes $699 shipping
Year:
2025
Make:
Toyota
Model:
Grand Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
White
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Gray
Transmission:
Automatic
Mileage:
26,451
Stock number:
28046103
VIN:
5TDAAAB5XSS080827

Preparing for a close up...

Photos coming soon

2025 Toyota Grand Highlander

XLE AWD

24,631 miles

$43,716

Fair Deal
Certified Pre-Owned
Palatine, IL
27 mi away
Year:
2025
Make:
Toyota
Model:
Grand Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
White
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
24,631
Stock number:
19837P
VIN:
5TDAAAB50SS088225

Preparing for a close up...

Photos coming soon

2025 Toyota Grand Highlander

XLE AWD

24,517 miles

$41,395

Good Deal
Des Plaines, IL
18 mi away
Year:
2025
Make:
Toyota
Model:
Grand 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:
Black
Transmission:
8-Speed Automatic
Mileage:
24,517
Stock number:
JU17860
VIN:
5TDAAAB50SS078181

Preparing for a close up...

Photos coming soon

2026 Toyota Grand Highlander

XLE FWD

518 miles

$46,488

Good Deal
Certified Pre-Owned
Elmhurst, IL
17 mi away
Year:
2026
Make:
Toyota
Model:
Grand Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Front-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
Storm Cloud
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Transmission:
8-Speed Automatic
Mileage:
518
Stock number:
12732P
VIN:
5TDAAAA58TS037137

Sponsored

  1. Home
  2. / Used Cars
  3. / Toyota Grand Highlander
  4. / Illinois
  5. / Chicago
Reviews
FAQs

4.7 Overall rating

(14 reviews)
Shanta C
5.0
Reviewed a 2024 Toyota Grand Highlander on Jun 20, 2024

Great suv with lots of space and safety features.

Nick A
5.0
Reviewed a 2024 Toyota Grand Highlander on Aug 14, 2024

The car is amazing. Not much of a discount though.

ashleigh D
5.0
Reviewed a 2024 Toyota Grand Highlander on Jun 02, 2024

I had a 2013 Buick enclave (which I absolutely loved but once it hit 100K nothing but mechanical problems) . I traded it in for a 2022 Highlander. I was miserable going from a larger suv to a much smaller one ( I didn’t realize how much smaller it actually was). So after having the highlander for less than two years , I traded it in for the Grand highlander. And it’s the absolute perfect size! I love it. No complaints so far. I almost bought a brand new top of the line telluride (that thing was fine and had every feature you could imagine) …. But after talking to a few mechanics I decided to spend a little more and get the Toyota.

Anonymous
5.0
Reviewed a 2024 Toyota Grand Highlander on May 21, 2024

It should be on $56000 out dealer price . Little high compared in online price

Patrick C
5.0
Reviewed a 2024 Toyota Grand Highlander on May 11, 2024

Great family vehicle comfortable and excellent leg room

Toyota Grand Highlander FAQs

How much does the Toyota Grand Highlander cost in Chicago, IL?

The average Toyota Grand Highlander costs about $44,188.46. The average price has decreased by -9.6% since last year. The 83 for sale near Chicago, IL on CarGurus, range from $39,779 to $56,666 in price.

Is the Toyota Grand Highlander a good car?

CarGurus experts gave the 2026 Toyota Grand Highlander an overall rating of 7.7/10 and Toyota Grand Highlander owners have rated the vehicle a 4.6/5 stars on average. If a vehicle has both strong expert and owner reviews, you can feel confident in its quality. If either expert reviews, owner reviews, or both are spotty, you might want to do some research to figure out where the car falls short.

How many Toyota Grand Highlander vehicles in Chicago, IL have no reported accidents or damage?

83 out of 83 for sale near Chicago, IL have no reported accidents or damage.

Is the Toyota Grand Highlander safe?

CarGurus experts gave the 2026 Toyota Grand Highlander a safety rating of 8/10.

What fuel types are available?

Gasoline engines are available.

  • 2026 Toyota Grand Highlander in Chicago IL

  • 2025 Toyota Grand Highlander in Chicago IL

  • 2024 Toyota Grand Highlander in Chicago IL

  • Used Toyota Grand Highlander for Sale Under $10,000 Near Chicago

  • Used Toyota Grand Highlander for Sale Under $15,000 Near Chicago

  • Used Toyota Grand Highlander for Sale Under $20,000 Near Chicago

  • Used Toyota Grand Highlander for Sale Under $25,000 Near Chicago

  • Used Toyota Grand Highlander for Sale Under $30,000 Near Chicago

  • Used Toyota Grand Highlander for Sale Under $40,000 Near Chicago

  • Used White Toyota Grand Highlander for Sale

  • Used Blue Toyota Grand Highlander for Sale

  • Used Red Toyota Grand Highlander for Sale

  • Used Black Toyota Grand Highlander for Sale

  • Used Silver Toyota Grand Highlander for Sale

  • Used Gray Toyota Grand Highlander for Sale

  • Toyota Grand Highlander XLE AWD

  • Toyota Grand Highlander XLE FWD

  • Toyota Grand Highlander Platinum AWD

  • Toyota Grand Highlander Limited AWD

  • Toyota Grand Highlander Limited FWD

  • Toyota Grand Highlander LE FWD in Chicago IL

  • Toyota Grand Highlander LE AWD in Chicago IL

  • Toyota Sedans for Sale in Chicago IL

  • Toyota SUVs & Crossovers for Sale in Chicago IL

  • Old Toyota Pickups for Sale in Chicago IL

  • Used Toyota Electric Cars for Sale

  • Reliable Cars For Sale in Chicago IL

  • Toyota Trucks for Sale in Chicago IL

  • Used Toyota Grand Highlander for Sale with Low Mileage

  • Used SUVs / Crossovers for Sale with Low Mileage

  • New Toyota Grand Highlander in Chicago IL

  • Certified Used Toyota Grand Highlander in Chicago IL

  • Toyota Grand Highlander in Palatine IL

  • Toyota Grand Highlander in Aurora IL

  • Toyota Grand Highlander in Kenosha WI

  • Toyota Grand Highlander in South Bend IN

  • Toyota Grand Highlander in Rockford IL

  • Toyota Grand Highlander in Milwaukee WI

  • Toyota Grand Highlander in Janesville WI

  • Toyota Grand Highlander in Holland MI

  • Toyota Grand 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

  • McGrath Elmhurst Toyota

  • Toyota of Fox Lake

  • Kenosha Toyota

  • Continental Toyota

  • Toyota On Western

  • Toyota of Merrillville

  • Toyota on Edens

  • Graff Toyota of Chesterton

  • Gerald Toyota of Matteson

  • Lombard Toyota

  • Classic Toyota

  • Oakbrook Toyota in Westmont

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

© 2026 CarGurus, Inc., All Rights Reserved.