There is no city that appreciates a convertible more than Chicago. The winters are brutal, the summers are perfect, and the city delivers roughly five months of drop-top weather that make owning a convertible feel earned. Lake Shore Drive with the top down at 8 PM in July. A Sunday drive up to Lake Geneva. A morning coffee run to Barrington in June. All of it works better in an open-top car.

At Autos of Chicago, we sell convertibles across every category — from BMW 4 Series Cabriolets to Mercedes C-Class Cabrios to Ford Mustang GTs to Porsche 911 Cabriolets. This guide ranks the best used convertibles for the way Chicago summers actually behave.

What Makes a Great Chicago-Summer Convertible

Before the rankings, three practical criteria:

Top-up refinement. Chicago summer weather changes in an hour. A convertible with a poorly sealed top is one heavy shower away from a soaked interior. Look for double-layer soft tops or retractable hardtops.
Trunk space with the top down. Retractable hardtops eat trunk space when folded. If you road-trip with luggage, verify the "top down" trunk capacity, not just the "top up" number.
Heated features for shoulder-season driving. May mornings can be 50°F. Heated seats and a heated steering wheel are what let you drive with the top down in April and October when everyone else is putting theirs up.

The Best Used Convertibles for Chicago Summers, Ranked

1. BMW 4 Series Convertible (F33 / G23) — The Complete Package

The 4 Series Cabriolet is the volume seller in this segment for a reason. Well-engineered soft top on newer G23 generation (2020+, replacing the retractable hardtop of the previous F33), strong xDrive AWD option for spring and fall driving, real four-seat capability, comfortable enough for a Chicago-to-Milwaukee run.

Engine choices: B48 2.0L turbo four (430i), B58 3.0L turbo inline-six (M440i).
Sweet spot: M440i xDrive Convertible with 20,000–50,000 miles. All-wheel drive for shoulder-season utility, inline-six for the driving experience.
Verdict: The best all-around convertible in this price range. Comfortable, quick, refined, and usable.

2. Mercedes-Benz C-Class Cabriolet (C300 / C43 AMG / C63) — The Elegant Choice

The C-Class Cabrio combines Mercedes interior quality with a fabric soft top that keeps the classic convertible profile. Airscarf neck-warmer vents make top-down driving comfortable into November.

Engine choices: M264 2.0L turbo four (C300), M276 3.0L twin-turbo V6 (C43 AMG), M177 4.0L twin-turbo V8 (C63).
Sweet spot: C43 AMG Cabriolet with 20,000–50,000 miles.
Verdict: The most refined interior of any convertible in its class. Buy the C43 for the best balance of performance and comfort.

3. Ford Mustang GT Convertible — The American Icon

The Mustang GT Convertible is what a summer American convertible has always been: 5.0L Coyote V8, six-speed manual (still available!), rear-drive, and an unashamed muscle-car character. The 2018+ refresh gave it a much better interior. The 2024+ S650 generation refined it further.

Engine: 5.0L Coyote V8, 460 hp (S550) / 480 hp (S650).
Sweet spot: 2018–2021 GT Convertible with the Performance Package.
Verdict: The soundtrack alone justifies the purchase. Best value in this ranking for pure fun-per-dollar.

4. Porsche 911 Cabriolet — The Reference

If your budget allows, the 911 Cabriolet is the sports-car convertible other convertibles are measured against. Flat-six sound, precision steering, all-wheel-drive available (Carrera 4S), and the retractable soft top folds and stows in twelve seconds at speeds up to thirty-one mph.

Sweet spot for value: 991.2 Carrera or Carrera S Cabriolet (2017–2019) with 25,000–50,000 miles.
Sweet spot for newest: 992-generation Carrera Cabriolet.
Verdict: Nothing else in this ranking delivers the same combination of daily-driver refinement and serious sports-car character.

5. Chevrolet Corvette Convertible (C7 / C8) — Serious Performance

The Corvette Convertible is a real sports car with a folding top. The C7 offered a soft top with excellent noise isolation. The C8 introduced a retractable hardtop that fits in twenty-eight seconds without eating meaningful trunk space.

Sweet spot for value: C7 Stingray Convertible (2015–2019) with 20,000–50,000 miles.
Sweet spot for new: C8 Stingray Convertible with Z51.
Verdict: See our C7 vs. C8 buyer's guide for the coupe/convertible math.

6. Audi A5 Cabriolet / S5 Cabriolet — Underrated Comfort

Audi's convertible in the compact luxury segment is often overlooked and is arguably the most comfortable long-distance cruiser in this price range. quattro all-wheel drive is standard on the S5, which extends drop-top season into shoulder months when a rear-drive convertible would be parked.

Engine: 2.0L turbo four (A5), 3.0L turbo V6 (S5).
Sweet spot: S5 Cabriolet 2018–2020 with quattro AWD.
Verdict: The quiet Audi answer to the BMW 4 Series and Mercedes C-Class. An underrated third option that deserves consideration.

7. Mazda MX-5 Miata — The Purist's Two-Seater

The Miata does not compete on power, luxury, or size. It competes on the driving experience — lightweight, rear-drive, six-speed manual, and one of the most engaging chassis at any price. If your budget is at the entry end of this list and a small, focused two-seater fits your life, the Miata delivers pure driving pleasure per dollar.

Sweet spot: ND-generation Miata (2016–present) Club with the Brembo/BBS package.
Verdict: A specific vehicle for a specific driver. Best when it is your second car, not your only convertible.

8. Jeep Wrangler / Ford Bronco — The Adventure Convertibles

The Wrangler and Bronco are convertibles by removing the roof, not by folding it. Completely different experience — off-road capable, harder-riding, no-nonsense open-air motoring for a very different kind of Chicago summer driver.

Sweet spot: Wrangler Rubicon Unlimited or Bronco Wildtrak with the removable hardtop.
Verdict: For buyers who want the top off and also want to take side trips to Wisconsin off-road parks.

What About the Boxster and BMW Z4?

Porsche 718 Boxster: exceptional. Focused two-seat mid-engine convertible. Buy the base Boxster or Boxster S — the four-cylinder turbos have polarized enthusiasts on sound but the driving experience is superb.
BMW Z4 (G29, 2019+): shares its platform with the Toyota Supra. Two-seat, rear-drive, straight-six or four-cylinder options. Better than its predecessor Z4. Compelling value on the used market.

Both are worth serious consideration if a two-seat convertible fits your life.

The Case Against Convertibles (In Chicago)

We would not be honest without noting the tradeoffs. Convertibles cost more to insure. Soft tops age and eventually leak. Retractable hardtops are complex mechanical systems. Trunk space with the top down is minimal. And if the convertible is your only car, you will be driving with the top up on 60% of the days when you want it down (because Chicago weather is unpredictable).

Buy a convertible if it will be your second car or your fair-weather car. Do not buy a convertible if it needs to be your daily driver in Illinois — the salt, cold, and 50°C internal-cabin temperatures in summer sun make it a compromise as a solo-vehicle.

Buy Your Summer Convertible at Autos of Chicago

We stock convertibles across every category — BMW 4 Series, Mercedes C-Class Cabriolet, Ford Mustang GT, Porsche 911 Cabriolet, Corvette, Audi S5 Cabriolet, and more. Every convertible we sell has been inspected in our service department, including a full top-mechanism check and interior sealing verification.

Browse Our Convertibles →

Call (224) 858-4007. 1555 E Rand Rd, Arlington Heights, IL 60004. Best months to shop for a summer convertible: April and May.