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 as the most accessible option in the lineup.

• Starting at $55,598
• 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.

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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 advanced features without the higher price of the Maybach. It's also the most popular trim in the lineup.

• Avg. market price: $55,598 (updated weekly)
• MPG/MPGe: 17 city / 25 hwy
• Inventory: 27 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 offers exclusive features and a more refined ride.

• Avg. market price: $55,598 (updated weekly)
• MPG/MPGe: 16 city / 24 hwy
• Inventory: 8 listings — lower availability; may limit negotiating room
• View Maybach S 580 Sedan 4MATIC listings

Trim Recommendations

Most Popular — S 580 Sedan 4MATIC

With 27 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 $55,598 avg market price — below the lineup median of $55,598 — 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 its fuel efficiency of 17/25 MPG.

Browse S 580 Sedan 4MATIC listings

These recommendations are based on CarGurus' proprietary market data from September 2, 2026, CarGurus experts' opinions, and generative AI.

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

Prices have softened 10.79% compared to this time last year, making it a favorable time to shop this model year.

There are 736 listings available, which gives you a meaningful amount of inventory 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, which lines up with its role as a flagship luxury sedan. The model scores 9/10 across Performance and Technology.

Owners consistently praise its luxurious feel, advanced technology, and remarkable performance, and many also call out the thrilling acceleration and enjoyable handling. In use, that fits a car meant to showcase Mercedes’ most advanced ideas rather than just serve as a comfortable cruiser.

The trade-offs are the high price and some complaints about the run-flat tires. Even so, the S-Class is aimed at buyers who want a prestige sedan with comfort, tech, and strong performance in one package, and 30.7% of listings are priced as good or great deals.

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 reliable, dependable, and trouble-free enough to inspire confidence, especially for buyers who want a luxury sedan they can count on over time. The expert review also emphasizes that Mercedes’ systems are designed to work smoothly and that the car’s advanced hardware is part of its long-term appeal.

Mercedes’ mild-hybrid setup adds electric assist for greater efficiency, and the brand’s four-year, 50,000-mile basic and powertrain warranties help cover early ownership. Still, because the S-Class is highly complex, you should expect maintenance discipline to matter a lot if you want to avoid expensive surprises later.

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

Accident-free inventory is solid at 81.9% — always verify the vehicle history report.

You should still run a history report on any car you’re considering, because a clean listing percentage does not replace a documented record. Prioritize a pre-purchase inspection, especially on a model with advanced electronics, suspension hardware, and luxury features that can be costly if neglected. Focus on overall condition, tire wear, and evidence that the car has been maintained carefully.

Key things to evaluate:

• Trim level: The S-Class launches with two configurations, and the base car already brings a high-end cabin, 19-inch wheels, a digital instrument cluster, and a large central touchscreen. The upper trim adds the more powerful V8 and is the better fit if you want stronger performance without stepping into a different model.
• 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 of torque. Both use EQ Boost mild-hybrid assistance and a nine-speed automatic.
• Safety package: Standard driver-assist 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. The suite is broad, but some of the most advanced features are still part of the car’s premium positioning.
• Infotainment: You get a 12.3-inch digital instrument cluster and a 12.8-inch OLED central touchscreen, plus wireless Apple CarPlay and Android Auto. The system also supports over-the-air-style sophistication through its updated MBUX setup, along with voice control and available rear-seat screens.
• Fuel efficiency: The trip computer averaged 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 full S-Class experience without paying for the V8. You still get the flagship cabin, the advanced infotainment setup, EQ Boost mild-hybrid assistance, and strong straight-line performance, so it covers the core appeal of the car very well.
• S580 4Matic: Choose this if you want the more powerful and more effortless version of the S-Class. The V8 brings 496 hp and 516 lb-ft of torque, making it the more satisfying pick for buyers who care most about performance and refinement.

The safety package is broad across the lineup, so you do not need to move up a trim just to get the core driver-assistance features.

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

This is a moderate market for selective buyers, with enough inventory and enough price softness to make comparison shopping worthwhile.

• Deal availability: 30.7% of listings are priced as good or great deals.
• Inventory: There are 736 listings available.
• Price trend: Prices have softened 10.79% compared with last year.
• Clean inventory: 81.9% of listings are accident-free.

If you find a listing below $59,183, 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 $59,183 sits slightly below last year's $66,338.

That decline suggests the market has already adjusted downward, which can help you as a buyer but may pressure future resale if prices keep easing. If you plan to sell later, buying well matters more than usual, because a lower entry price gives you more room to absorb depreciation. The good news is that strong demand for flagship luxury sedans can still support values when the car is well kept and properly equipped.

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 not have crash-test ratings from NHTSA or IIHS available.

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 includes an industry-first rear-passenger airbag.

The main caveat is that this is a freshly redesigned, expensive, low-volume car, so formal crash-test coverage is limited. Even with a strong standard safety suite, you should still verify that all driver-assistance systems work properly during a test drive.

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:

• 30.7% of listings are priced as good or great deals.
• Accident-free inventory is solid at 81.9% — always verify the vehicle history report.
• Price trend: Prices have softened 10.79% compared with last year.
• Owners rate it 4/5 — a solid satisfaction signal.
• The redesigned model brings a more sophisticated infotainment system, new powertrains, and a stronger flagship-tech focus.

Consider the 2022 if:

• At $63,800, the 2022 costs more than the current year's $59,183 average.
• It adds a 48-volt mild-hybrid setup with updated flagship luxury and a choice of inline-six or V8 power.

The bottom line: If you want the best mix of price relief, inventory, and the redesigned S-Class experience, the 2021 is the smarter buy. If you’re willing to pay more for the next model year’s updated execution and don’t mind the higher average price, the 2022 is the cleaner alternative.

These recommendations are based on CarGurus' proprietary market data from September 11, 2026, CarGurus experts' opinions, and generative AI.