Used 2021 Mercedes-Benz S-Class for Sale nearChicago, IL

Compare 2021 Mercedes-Benz S-Class Trims in Chicago, IL

The S-Class offers a blend of luxury and performance, with the S 580 Sedan 4MATIC being the most accessible option in the lineup.

• Starting at $53,625
• Best MPG/MPGe: 17 city / 25 hwy
• Most Popular: S 580 Sedan 4MATIC

Trim Overview

Prices updated weekly from CarGurus listings.

Quick Compare Table

Listing prices sourced from CarGurus — updated weekly. OEM specs from manufacturer data.

Missing data displayed as "—".

Trim Deep Dives

S 580 Sedan 4MATIC — "Who It's For"

The S 580 Sedan 4MATIC is the pick for shoppers who want luxury and performance without the high price of the Maybach. It's also the most popular trim in the lineup.

• Avg. market price: $53,625 (updated weekly)
• MPG/MPGe: 17 city / 25 hwy
• Inventory: 31 listings
• View S 580 Sedan 4MATIC listings

Maybach S 580 Sedan 4MATIC — "Who It's For"

The Maybach S 580 Sedan 4MATIC is the pick for shoppers who want the ultimate luxury experience without compromising on performance. It's a premium choice for those seeking exclusivity.

• Avg. market price: $109,991 (updated weekly)
• MPG/MPGe: 16 city / 24 hwy
• Inventory: 10 listings — lower availability; may limit negotiating room
• View Maybach S 580 Sedan 4MATIC listings

Trim Recommendations

Most Popular — S 580 Sedan 4MATIC

With 31 active listings, the S 580 Sedan 4MATIC is the clear volume leader in the lineup.

Browse S 580 Sedan 4MATIC listings

Best Budget Option — S 580 Sedan 4MATIC

At $53,625 avg market price — below the lineup median of $81,808 — it's the most accessible entry point.

Browse S 580 Sedan 4MATIC listings

Best for Fuel Economy — S 580 Sedan 4MATIC

The S 580 Sedan 4MATIC leads the lineup with 17/25 MPG/MPGe.

Browse S 580 Sedan 4MATIC listings

These recommendations are based on CarGurus' proprietary market data from October 29, 2026, CarGurus experts' opinions, and generative AI.

How much does the 2021 Mercedes-Benz S-Class cost?

Prices have softened 8.60% compared to this time last year, making it a favorable time to shop this model year.

There are 723 listings available, which gives you a solid pool of used S-Class options to compare.

Is the 2021 Mercedes-Benz S-Class a good car?

Generally — the 2021 Mercedes-Benz S-Class earns a 4/5 user rating and a 7.5/10 expert rating. The model scores 9/10 across Performance and Technology.

Owners consistently praise its luxurious feel, advanced technology, and remarkable performance. The review also points to thrilling acceleration and enjoyable handling, while the S-Class’s role as a flagship luxury sedan and technology showcase fits buyers who want a top-tier executive car.

The main trade-offs are its high price and some run-flat tire complaints. It also leans more toward comfort and refinement than pure driver engagement.

With 33.7% of listings marked as good or great deals, you have some room to shop selectively.

Is the 2021 Mercedes-Benz S-Class reliable?

Owners rate it 4/5, a solid signal of long-term satisfaction.

The owner feedback points to a car that feels luxurious, advanced, and enjoyable to live with over time. It also suggests the S-Class delivers the kind of comfort and performance that can make it feel dependable in daily use, especially when you want a flagship sedan you can count on.

Mercedes’ performance notes reinforce that impression with a smooth nine-speed automatic, mild-hybrid assistance, and a chassis tuned for composure and comfort. The brand also backs it with a four-year, 50,000-mile basic warranty and a four-year, 50,000-mile powertrain warranty.

Because the S-Class is complex and expensive to maintain, long-term ownership risk rises if prior care was inconsistent.

What should I look for when buying a used 2021 Mercedes-Benz S-Class?

Accident-free inventory is solid at 79.5% — always verify the vehicle history report.

You should still run a history report on every candidate, even if the listing looks clean. Prioritize a pre-purchase inspection, especially on a car with advanced electronics, driver-assist systems, and a complex mild-hybrid setup. Focus on overall condition, tire wear, and evidence of careful maintenance.

Key things to evaluate:

• Trim level: The S-Class launches in two configurations, and both are loaded with luxury and technology. The base S500 4Matic already brings a strong equipment set, while the S580 4Matic adds more power and is the better fit if you want the most performance. The base trim still leaves some desirable items as options, so check carefully for the equipment you want.
• Powertrain: The S500 4Matic uses a 3.0-liter turbocharged inline-six with 429 horsepower and 384 pound-feet of torque, while the S580 4Matic uses a 4.0-liter twin-turbo V8 with 496 hp and 516 lb-ft. Both use a nine-speed automatic and EQ Boost mild-hybrid assistance.
• Safety package: Standard driver-assistance features include adaptive cruise control with stop-and-go, automated lane centering, automatic emergency braking, forward-collision warning, blind-spot monitoring, lane-keep assist, lane-change assist, traffic-sign recognition, a driver-attention monitor, and a 360-degree camera system. Mercedes also includes an industry-first rear-passenger airbag.
• Infotainment: The standard setup includes a 12.3-inch digital instrument cluster and a 12.8-inch OLED central touchscreen, plus wireless Apple CarPlay and Android Auto. It also includes six USB ports, and the system supports augmented-reality head-up display functionality.
• Fuel efficiency: EPA fuel-economy ratings aren’t available yet, but the trip computer showed 22.4 mpg over about 300 miles of driving.

Which 2021 Mercedes-Benz S-Class trim should I buy?

The 2021 Mercedes-Benz S-Class is offered in 2 trim levels: S500 4Matic and S580 4Matic.

Here's the short version:

• S500 4Matic: This is the better-value choice if you want the core S-Class experience with the 429-hp inline-six, EQ Boost, all-wheel drive, and the full luxury-and-tech mission of the car. It delivers the flagship feel without stepping all the way up to the V8.
• S580 4Matic: Choose this if you want the strongest performance in the lineup. The V8 adds more power and torque, making it the right pick if you want the most effortless acceleration and don’t mind paying more.

The safety package is strong across the lineup, with standard adaptive cruise control, lane centering, automatic emergency braking, blind-spot monitoring, and a 360-degree camera system.

Is now a good time to buy a used 2021 Mercedes-Benz S-Class?

This is a moderate market for selective buyers, so you can shop carefully and still find worthwhile listings.

• Deal availability: 33.7% of listings are priced as good or great deals.
• Inventory: There are 723 listings available.
• Price trend: Prices have softened 8.60% compared with last year.
• Clean inventory: 79.5% of listings are accident-free.

If you find a listing below $57,678, that's toward the low end of the year-round range and worth acting on quickly.

What is the 2021 Mercedes-Benz S-Class's resale value?

The current average of $58,286 sits slightly below last year's $63,767.

That price movement suggests the market has already absorbed some depreciation, which can help future resale stability if you buy at the right number. A softer current market can also make it easier for you to avoid overpaying, which matters when you eventually go to sell.

Because the S-Class remains a flagship luxury sedan with strong owner satisfaction, it should continue to attract shoppers who want prestige and technology. Vehicles with solid owner satisfaction ratings, like this model year's 4/5, tend to retain buyer demand, which supports resale value over time.

Is the 2021 Mercedes-Benz S-Class safe?

The S-Class does get a plethora of safety features, including an industry-first rear-passenger airbag.

It earns a 7/10 safety score from our experts.

Standard driver-assistance features include adaptive cruise control with stop-and-go functionality, automated lane centering, automatic emergency braking, forward-collision warning, blind-spot monitoring, lane-keep assist, lane-change assist, traffic-sign recognition, a driver-attention monitor, and a 360-degree camera system. Mercedes also says the lane-keep assist can read road edges, and the adaptive cruise and lane-centering systems performed especially well in testing.

Crash-test ratings from NHTSA and IIHS aren’t available, so you’ll want to lean on the standard safety equipment and the car’s strong driver-assist performance when evaluating it.

Should I buy a 2021 Mercedes-Benz S-Class or consider a different year?

If you're weighing the 2021 against nearby model years, here's how to think about it:

Choose the 2021 if:

• 33.7% of listings are priced as good or great deals.
• Accident-free inventory is solid at 79.5% — always verify the vehicle history report.
• Price trend: Prices have softened 8.60% compared with last year.
• Owners rate it 4/5 — a solid satisfaction signal.
• The redesign brings a more sophisticated infotainment system, new powertrains, and more aerodynamic bodywork.

Consider the 2022 if:

• At $61,720, the 2022 costs more than the current year's $58,286 average.
• It adds a 48-volt mild-hybrid setup with updated EPA estimates and a slightly newer model-year package.

The bottom line: If you want the better value, the 2021 is the smarter buy because prices have softened and inventory is healthy. If you’re willing to pay more for a newer model year, the 2022 is the cleaner alternative.

How does the 2021 Mercedes-Benz S-Class compare to the 2021 BMW 7 Series?

These recommendations are based on CarGurus' proprietary market data from November 3, 2026, CarGurus experts' opinions, and generative AI.