Enterprise
Convertible Rentals in Los Angeles

Convertible Rental in Chicago

Enjoy your drive even more by renting a convertible from Enterprise. Soak up the sun or view the night stars. This type of car is perfect for road trips and weekend getaways. Reserve a convertible online and pick up at a branch near you.

Explore Convertible Rental Options

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FAQs for Renting Convertibles in Chicago

Convertibles are considered higher-performance vehicles and, therefore, require the renter to be 25 or older. People under 25 have the option to rent several other vehicle types, including sedans, SUVs, and vans.

The price of renting a convertible will vary depending on seasonality, location, insurance, and more. We recommend you start a reservation above for the most accurate pricing.

Enterprise offers the Ford Mustang and similar models in our lineup of convertibles. If you're looking for a luxury convertible such as a BMW 430i, check out our partner brand, Exotic Car Collection by Enterprise. Start a reservation above to see our available stock. Please note, we cannot guarantee availability on specific car models.

Popular Road Trips from Chicago

Chicago is the perfect starting point for a quick escape or a weekend adventure. From lakeside towns to vibrant cities and scenic parks, there’s no shortage of places to explore just a few hours from downtown. Grab your rental car and hit the road to discover what the Midwest has to offer.

st. louis arch

Chicago to St. Louis

302 miles (4 hours, 46 minutes)

Head south to St. Louis in about five hours for a mix of iconic landmarks, barbecue, and riverfront charm. Stop in Springfield for a dose of Route 66 nostalgia. Once in town, visit the Gateway Arch, explore Forest Park, and stroll through historic neighborhoods.

milwaukee

Chicago to Milwaukee

102 miles (1 hour, 51 minutes)

Milwaukee offers a laid-back vibe with lakefront views, craft breweries, and cultural gems. Take the scenic route along Lake Michigan for small-town stops and shoreline views. Once there, enjoy the Milwaukee Public Market, Harley-Davidson Museum, and local beer halls.

detroit

Chicago to Detroit

284 miles (4 hours, 27 minutes)

Drive about five hours east to Detroit for a city full of history, innovation, and a growing arts scene. Stop in Ann Arbor for a quick bite or a walk through campus. In Detroit, explore the revitalized riverfront, Motown Museum, and vibrant neighborhoods like Corktown.

grand rapids

Chicago to Grand Rapids, MI

179 miles (2 hours, 52 minutes)

In just under three hours, Grand Rapids welcomes you with a thriving art scene and access to Lake Michigan beaches. Take a detour through Holland or Saugatuck for small-town charm. Once in Grand Rapids, check out the Frederik Meijer Gardens and local food spots.

Indiana Sand Dunes

Chicago to Indiana Dunes National Park

38 miles (52 minutes)

Only about an hour away, Indiana Dunes offers a quick nature escape with sandy beaches, hiking trails, and lakefront views. Pack a picnic and spend the day exploring dunes, wetlands, and forests. It’s the perfect spot for a spontaneous outdoor getaway.

madison, wi

Chicago to Madison, WI

147 miles (2 hours, 47 minutes)

Head North to Madison and discover a lively college town surrounded by lakes that's full of local flavor. Stop in Rockford or grab cheese curds along the way. Once there, explore the Capitol Square, bike the lakeside trails, and enjoy the city’s farm-to-table food scene.

indianapolis

Chicago to Indianapolis

184 miles (3 hours, 5 minutes)

Head South to Indianapolis for sports, museums, and a walkable downtown. Consider a stop in Lafayette or Fair Oaks Farms for a fun break. Once in Indy, visit the Indianapolis Motor Speedway, stroll the Canal Walk, and check out local eats in Fountain Square.

One-Way Car Rental

Looking to rent a car for a one-way trip? Enterprise Rent-A-Car offers convenient one-way car rentals. We have a great selection of vehicles for trips across the city, across the country or from the airport.

One-Way Car Rental

Long-Term Car Rental

This is ideal for corporate relocations, temporary work assignments, extended trips, and much more. It can also be used while waiting for a new fleet car. 

Long-Term Car Rental