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 $56,484
• 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 features without the high price of the Maybach. It's also the most popular trim in the lineup.

• Avg. market price: $56,484 (updated weekly)
• MPG/MPGe: 17 city / 25 hwy
• Inventory: 32 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. Its exclusivity makes it a standout choice.

• Avg. market price: $56,484 (updated weekly)
• MPG/MPGe: 16 city / 24 hwy
• Inventory: 7 listings — lower availability; may limit negotiating room
• View Maybach S 580 Sedan 4MATIC listings

Trim Recommendations

Most Popular — S 580 Sedan 4MATIC

With 32 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 $56,484 avg market price — below the lineup median of $56,484 — 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 12, 2026, CarGurus experts' opinions, and generative AI.

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

Prices have softened 10.60% compared to this time last year, making it a favorable time to shop this model year.

There are 739 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 points to a strong overall showing. The model scores 9/10 across Performance and Technology.

Owners consistently praise its luxurious feel, advanced technology, and remarkable performance, with many also calling out the thrilling acceleration and handling. The main trade-off is the high price, and the expert review also notes that some competitors are a bit quicker and that highway wind noise is more noticeable than expected.

For you, that means this is a flagship sedan best suited to buyers who want a top-tier luxury experience and are willing to pay for it. With 32.7% of listings marked as good or great deals, the market gives you 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 reliable, dependable, and trouble-free in the ways that matter most to luxury buyers, especially when you want a sedan you can count on over time. The expert review also emphasizes the S-Class’s strong execution and the way its systems work smoothly in daily use, which supports the impression of a well-sorted flagship.

Mercedes also includes a four-year, 50,000-mile basic warranty and a four-year, 50,000-mile powertrain warranty. Because this is a highly complex luxury sedan, long-term ownership risk is still tied to maintenance discipline and repair costs if the car has been neglected.

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

Accident-free inventory is solid at 82.3% — always verify the vehicle history report.

You should still check the report carefully, because a clean listing percentage does not replace a proper history review. Prioritize a pre-purchase inspection that focuses on electronics, suspension behavior, and any signs of expensive wear. On a car like this, condition matters as much as mileage, especially if you want to avoid surprise repair bills.

Key things to evaluate:

• Trim level: The S500 4Matic is the entry point, while the S580 4Matic adds the V8 and more power. The base setup already brings a lot of luxury and technology, so the cheaper trim is the value play if you want the flagship experience without paying for the stronger engine.
• 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. The rear-passenger airbag is also standard.
• 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 software sophistication through the updated MBUX setup, along with voice control and biometric or facial-recognition profiles.
• Fuel efficiency: Mercedes does not provide EPA fuel-economy ratings here, though the test car averaged 22.4 mpg over about 300 miles.

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

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

Here's the short version:

• S500 4Matic: This is the better-value choice if you want the S-Class experience with the lower starting price. It still gives you the full flagship feel, the mild-hybrid setup, and plenty of power, so it should satisfy most luxury buyers without pushing you into the pricier V8.
• S580 4Matic: Choose this if you want the stronger engine and the most effortless performance. It adds more horsepower and torque, making it the right pick if you care most about straight-line speed and want the more powerful version of the lineup.

The safety content does not call out trim-specific safety-package gaps, so you should compare equipment carefully on individual listings.

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

This looks like a moderate, selective buyer’s market, so you can shop patiently but should move quickly on the right car.

• Deal availability: 32.7% of listings are priced as good or great deals.
• Inventory: There are 739 listings available.
• Price trend: Prices have softened 10.60% compared with last year.
• Clean inventory: 82.3% of listings are accident-free.

If you find a listing below $59,063, 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 $59,063 sits slightly below last year's $66,070.

That decline suggests the market has already adjusted downward, which can help you as a buyer today but may limit upside if you plan to resell soon. For a future seller, the key takeaway is that this model year is pricing more competitively now than it did a year ago, so holding value will depend heavily on condition, mileage, and equipment.

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?

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

Crash-test ratings from NHTSA and IIHS aren’t available for this model year. Even so, the S-Class comes standard with a broad driver-assistance suite that includes 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. The expert review says the lane-centering and adaptive cruise systems work better than many rivals, especially on highway curves and in traffic. The main caveat is that the car’s safety reputation here rests on equipment and system performance rather than published crash-test results.

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:

• 32.7% of listings are priced as good or great deals.
• Accident-free inventory is solid at 82.3% — always verify the vehicle history report.
• Price trend: Prices have softened 10.60% compared with last year.
• Owners rate it 4/5 — a solid satisfaction signal.
• It introduces a redesigned cabin, new powertrains, and more advanced infotainment.

Consider the 2022 if:

• At $63,618, the 2022 costs more than the current year's $59,063 average.
• It adds a more polished full-size luxury-sedan presentation with a similar mild-hybrid powertrain lineup.

The bottom line: If you want the better value, the 2021 is the smarter target because prices have eased and inventory is healthy. If you’re willing to spend more for a newer model year, the 2022 is the cleaner alternative, but price-sensitive buyers should focus on the 2021 and shop for a well-kept example with strong equipment.

These recommendations are based on CarGurus' proprietary market data from September 15, 2026, CarGurus experts' opinions, and generative AI.