CoPilot AI-Assisted Car Shopping

 New Search
 Save
 Sort
 Share

Used Toyota Sienna for Sale in Chicago, IL

Siennas for Sale at Dealers

Filters
Price
Year
Mileage
Trim
2020 Toyota Sienna XLE FWD photo
2020 Toyota Sienna XLE FWD • Joliet, IL
Blue • 3.5L V6 Engine
$19,999 • 135.8k miles
•••

#95 2015-2023 Toyota Sienna

CoPilot AI: It’s a “D+” Buy

  • Dealer Rating - 4.4 stars
More details
2023 Toyota Sienna XSE AWD photo
Price Drop
2023 Toyota Sienna XSE AWD • Lake Geneva, WI
Gray • 2.5L I4 Engine
$48,600 • 35.7k miles
•••

#108 2015-2023 Toyota Sienna

CoPilot AI: It’s a “D-” Buy

  • $497 Price Drop
  • CARFAX: One Owner
  • Motivation to Negotiate - Increasing
More details
2022 Toyota Sienna LE FWD photo
2022 Toyota Sienna LE FWD • Elkhart, IN
Black • 2.5L I4 Engine
$19,900 • 198.8k miles
•••

#86 2015-2023 Toyota Sienna

CoPilot AI: It’s a “C” Buy

  • Fair Price - $482 Above Market
  • CARFAX: One Owner
  • Dealer Rating - 4.7 stars
More details
2015 Toyota Sienna XLE Premium AWD photo
2015 Toyota Sienna XLE Premium AWD • West Allis, WI
3.5L V6 Engine
$21,999 • 99.1k miles
•••

#102 2015-2023 Toyota Sienna

CoPilot AI: It’s a “D-” Buy

  • Motivation to Negotiate - Increasing
  • Very Low Mileage
  • Dealer Rating - 4.3 stars
More details
2019 Toyota Sienna XLE Auto Access Seat FWD photo
Price Drop
2019 Toyota Sienna XLE Auto Access Seat FWD • Downers Grove, IL
3.5L V6 Engine
$43,067 • 42.7k miles
•••
More details
2017 Toyota Sienna XLE FWD photo
16
2017 Toyota Sienna XLE FWD • Gurnee, IL
3.5L V6 Engine
$24,999 • 47.1k miles
•••

#16 2015-2023 Toyota Sienna

CoPilot AI: It’s a “B+” Buy

  • Great Price - $1,855 Below Market
  • Motivation to Negotiate - Increasing
  • Very Low Mileage
More details
2018 Toyota Sienna L FWD photo
Price Drop
2018 Toyota Sienna L FWD • Elgin, IL
White • 3.5L V6 Engine
$14,499 • 143.2k miles
•••

#94 2015-2023 Toyota Sienna

CoPilot AI: It’s a “D+” Buy

  • $500 Price Drop
  • Motivation to Negotiate - Very High
  • Dealer Rating - 4.4 stars
More details
2021 Toyota Sienna XLE FWD photo
Price Drop
2021 Toyota Sienna XLE FWD • Northlake, IL
White • 2.5L I4 Engine
$29,969
•••
More details
2015 Toyota Sienna XLE FWD photo
2015 Toyota Sienna XLE FWD • Rolling Meadows, IL
Silver • 3.5L V6 Engine
$19,900 • 77.5k miles
•••

#49 2015-2023 Toyota Sienna

CoPilot AI: It’s a “B-” Buy

  • Fair Price - $215 Below Market
  • Very Low Mileage
  • Dealer Rating - 4.1 stars
More details
2023 Toyota Sienna XLE FWD photo
2023 Toyota Sienna XLE FWD • Oak Lawn, IL
White • 2.5L I4 Engine
$45,195 • 16.9k miles • Certified
•••

#30 2015-2023 Toyota Sienna

CoPilot AI: It’s a “B” Buy

  • Good Price - $1,465 Below Market
  • CARFAX: One Owner
  • Motivation to Negotiate - High
More details
2017 Toyota Sienna LE FWD photo
2017 Toyota Sienna LE FWD • McHenry, IL
3.5L V6 Engine
$17,500 • 118.4k miles
•••

#111 2015-2023 Toyota Sienna

CoPilot AI: It’s a “F” Buy

  • Motivation to Negotiate - Increasing
  • Average Mileage
More details
2016 Toyota Sienna XLE FWD photo
6
2016 Toyota Sienna XLE FWD • Elkhorn, WI
Red • 3.5L V6 Engine
$13,405 • 141.1k miles
•••

#6 2015-2023 Toyota Sienna

CoPilot AI: It’s a “B+” Buy

  • Great Price - $2,912 Below Market
  • Average Mileage
More details
2016 Toyota Sienna LE AWD photo
Price Drop
2016 Toyota Sienna LE AWD • Chicago, IL
Silver • 3.5L V6 Engine
$14,895 • 137.9k miles
•••

#74 2015-2023 Toyota Sienna

CoPilot AI: It’s a “C+” Buy

  • $100 Price Drop
  • Fair Price - $228 Above Market
  • CARFAX: One Owner
More details
2015 Toyota Sienna SE FWD photo
2015 Toyota Sienna SE FWD • Waukesha, WI
Black • 3.5L V6 Engine
$15,390 • 145.1k miles
•••

#75 2015-2023 Toyota Sienna

CoPilot AI: It’s a “C+” Buy

  • Fair Price - $236 Above Market
  • Includes $348 Premium Upgrades
  • CARFAX: One Owner
More details
2016 Toyota Sienna XLE Premium AWD photo
2016 Toyota Sienna XLE Premium AWD • Lincolnwood, IL
Black • 3.5L V6 Engine
$26,373 • 59.1k miles
•••

#101 2015-2023 Toyota Sienna

CoPilot AI: It’s a “D-” Buy

  • Includes $288 Premium Upgrades
  • Motivation to Negotiate - Very High
  • Very Low Mileage
More details
2020 Toyota Sienna L FWD photo
Price Drop
2020 Toyota Sienna L FWD • Milwaukee, WI
Black • 3.5L V6 Engine
$28,826 • 53.6k miles
•••

#34 2015-2023 Toyota Sienna

CoPilot AI: It’s a “B” Buy

  • $473 Price Drop
  • Good Price - $975 Below Market
  • Very Low Mileage
More details
2022 Toyota Sienna Platinum AWD photo
7
2022 Toyota Sienna Platinum AWD • Milwaukee, WI
White • 2.5L I4 Engine
$43,995 • 48.5k miles
•••

#7 2015-2023 Toyota Sienna

CoPilot AI: It’s a “B+” Buy

  • Great Price - $2,846 Below Market
  • Includes $1,292 Premium Upgrades
  • Motivation to Negotiate - Very High
More details
2021 Toyota Sienna LE FWD photo
2021 Toyota Sienna LE FWD • Michigan City, IN
Silver • 2.5L I4 Engine
$33,999 • 48.6k miles
•••

#32 2015-2023 Toyota Sienna

CoPilot AI: It’s a “B” Buy

  • Good Price - $1,304 Below Market
  • Motivation to Negotiate - Very High
  • Very Low Mileage
More details
2017 Toyota Sienna XLE AWD photo
20
2017 Toyota Sienna XLE AWD • Libertyville, IL
Blue • 3.5L V6 Engine
$12,990 • 167.2k miles
•••

#20 2015-2023 Toyota Sienna

CoPilot AI: It’s a “B+” Buy

  • Great Price - $1,512 Below Market
  • Includes $255 Premium Upgrades
  • CARFAX: One Owner
More details
2018 Toyota Sienna XLE Premium FWD photo
Price Drop
2018 Toyota Sienna XLE Premium FWD • Addison, IL
Silver • 3.5L V6 Engine
$25,550 • 75.4k miles
•••

#48 2015-2023 Toyota Sienna

CoPilot AI: It’s a “B-” Buy

  • $400 Price Drop
  • Fair Price - $231 Below Market
  • Includes $202 Premium Upgrades
More details
2022 Toyota Sienna XLE FWD photo
2022 Toyota Sienna XLE FWD • Libertyville, IL
Silver • 2.5L I4 Engine
$36,926 • 53.9k miles
•••

#61 2015-2023 Toyota Sienna

CoPilot AI: It’s a “C+” Buy

  • Fair Price - $390 Below Market
  • CARFAX: One Owner
  • Motivation to Negotiate - Increasing
More details
2020 Toyota Sienna L FWD photo
Price Drop
2020 Toyota Sienna L FWD • Peru, IL
Blue • 3.5L V6 Engine
$29,348 • 51.4k miles
•••

#91 2015-2023 Toyota Sienna

CoPilot AI: It’s a “C-” Buy

  • $517 Price Drop
  • CARFAX: One Owner
  • Motivation to Negotiate - Increasing
More details
2020 Toyota Sienna L FWD photo
2020 Toyota Sienna L FWD • Chicago, IL
White • 3.5L V6 Engine
$17,995 • 143.4k miles
•••

#28 2015-2023 Toyota Sienna

CoPilot AI: It’s a “B” Buy

  • Great Price - $2,943 Below Market
  • Motivation to Negotiate - High
  • Dealer Rating - 4.6 stars
More details
2018 Toyota Sienna XLE FWD photo
2018 Toyota Sienna XLE FWD • Waukesha, WI
Black • 3.5L V6 Engine
$23,397 • 91.1k miles
•••

#54 2015-2023 Toyota Sienna

CoPilot AI: It’s a “B-” Buy

  • Fair Price - $276 Above Market
  • Includes $1,049 Premium Upgrades
  • Motivation to Negotiate - Increasing
More details
2017 Toyota Sienna LE FWD photo
Price Drop
2017 Toyota Sienna LE FWD • New Lenox, IL
Gray • 3.5L V6 Engine
$17,795 • 103.8k miles
•••

#66 2015-2023 Toyota Sienna

CoPilot AI: It’s a “C+” Buy

  • $100 Price Drop
  • Fair Price - $28 Below Market
  • Includes $211 Premium Upgrades
More details
1-25 of 165 results
HomeToyotaSienna

2026 Toyota Sienna

Minivan
Seats
8
Fuel Economy
36City MPG
36Hwy MPG
NHTSA Rating Summary
Dimensions
Toyota Sienna for Sale by City
Research More Models
View more Minivans

© 2026 CoPilot. All Rights Reserved.