7 live listingsUpdated
Used Bentley for sale in Chicago, IL
We're tracking 7 used Bentleys for sale in Chicago, IL right now, priced from $95,300 to $306,338 with a median asking price of $127,911. Model years range from 2019 to 2025 and the typical car shows 38,100 mi.
That's 1% of the 775 used Bentleys we track nationwide. Comparing the same model, year and trim, the typical Bentley here is listed 8% below similar cars elsewhere in the US (7 cars compared).
The lowest-priced one is a 2019 Bentley Bentayga V8 listed at $95,300 with 19,249 mi in Chicago, IL.
Best Bentley deals in Chicago, IL
3 deals priced below market right now, the best by about $30,519. Members get the VIN, dealer, listing link and a ready-to-send negotiation email for each one.
-
$31k below market Locked2025 Bentley Continental
Gen III GTC Speed
Great deal: about $31k under fair value for its year, trim and miles.
Asking price $306,338Deal score 96 -
$13k below market Locked
2023 Bentley Bentayga
Gen II S V8
Great deal: about $13k under fair value for its year, trim and miles.
Asking price $127,911Deal score 93 -
$10k below market Locked
2021 Bentley Bentayga
Gen II V8
Great deal: about $10k under fair value for its year, trim and miles.
Asking price $97,868Deal score 92
Members see every deal's VIN, dealer and listing link, plus a negotiation email.
Bentley models for sale in Chicago, IL
| Model | For sale | Lowest price | Median price |
|---|---|---|---|
| Bentley Bentayga | 5 | $95,300 | $127,911 |
| Bentley Continental | 2 | $125,418 | $215,878 |
Latest used Bentleys in Chicago, IL
-
2020 Bentley Continental
Gen III GT V8
Asking price $125,418 -
2025 Bentley Continental
Gen III GTC Speed
Asking price $306,338 -
2023 Bentley Bentayga
Gen II V8
Asking price $131,991 -
2021 Bentley Bentayga
Gen II V8
Asking price $97,868 -
2023 Bentley Bentayga
Gen II S V8
Asking price $127,911 -
2023 Bentley Bentayga
Gen II Hybrid
Asking price $134,447 -
2019 Bentley Bentayga
Gen I V8
Asking price $95,300
Chicago, IL vs. the rest of the US
Comparing the same model, year and trim, the typical Bentley here is listed 8% below similar cars elsewhere. The medians below also reflect which years and trims are listed in each place.
| Location | For sale | Median price | Lowest price | Median miles |
|---|---|---|---|---|
| Chicago, IL | 7 | $127,911 | $95,300 | 38,100 |
| Rest of the US | 768 | $149,889 | $20,149 | 21,543 |
Other Illinois cities
Used Bentleys in Chicago, IL: common questions
How much does a used Bentley cost in Chicago, IL?
Used Bentley asking prices in Chicago, IL currently range from $95,300 to $306,338, with a median of $127,911 across 7 listings.
Are used Bentleys cheaper in Chicago, IL?
Yes. Comparing the same model, year and trim, used Bentleys in Chicago, IL are listed a median 8% below similar cars elsewhere in the US, across 7 cars with matches. Mileage, options and condition still vary from car to car.
Which Bentley models are for sale in Chicago, IL?
The most listed are the Bentley Bentayga (5 cars, median $127,911) and the Bentley Continental (2 cars, median $215,878).
What is the cheapest Bentley for sale right now in Chicago, IL?
The lowest asking price in our latest scan is a 2019 Bentley Bentayga V8 listed at $95,300 with 19,249 mi in Chicago, IL.
How many miles do used Bentleys for sale in Chicago, IL have?
The median Bentley for sale in Chicago, IL shows 38,100 mi. 1 of 7 listings (14%) have under 15,000 miles.
How long do Bentleys stay on the market in Chicago, IL?
Current Bentley listings in Chicago, IL have been for sale for a median of 74 days. Cars that sit well beyond that are often the easiest to negotiate on.
How current is this data?
These numbers come from our latest scan of dealer listings on Nov 1, 2026. Luxury Car Deals rescans the market regularly and removes cars that have sold.