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Chicago Car Rental

Enterprise Car Rental Locations in Chicago

A rental car from Enterprise Rent-A-Car is perfect for road trips, airport travel or to get around town on weekends. Visit one of our many convenient neighborhood car rental locations in Chicago, or find cheap car rental rates at O'Hare (ORD) or Midway (MDW) International Airports.

Airport Locations

Exotics Locations

Neighborhood Locations

Things to Do

Explore Chicago

Visit Millennium Park, walk the Magnificent Mile, dine at Billy Goat Tavern or catch a game at Wrigley Field.

Benefits of Booking Direct

Low Rates & Quality Service

Earn points towards free rental days with Enterprise Plus and take advantage of our award-winning customer service.

Offers

Find Cheap Car Rental Rates

Get away this weekend in a rental car and enjoy great low rates.

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Popular Rental Cars in Chicago

Find the perfect vehicle for your needs.

suv rental

SUVs

Whether you are going on a weekend family trip or exploring the countryside we are sure to have the ideal SUV for your needs.

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pickup truck rental

Pickup Trucks

Our pickup trucks have the space, power and durability you need for hauling large items or taking a weekend retreat.

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luxury car rental

Luxury Cars

Choose from our range of premium cars and SUVs to rent, including convertibles, coupes, hybrids and more.

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Chicago Car Rental FAQs

For additional questions, please visit our main car rental FAQs page.

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.

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Chicago Car Sales

Looking to buy? We sell cars, too. Shop our selection of quality used cars, trucks, vans and SUVs. And, when you’re ready, experience the Enterprise customer service you know and expect.

Chicago Exotic Car Rental

In Chicago, we offer exotic sports cars, luxury sedans and SUVs, and have one of the largest selections of exotic and premium vehicle rentals available.

Chicago Truck Rental

Need a truck? Our moving trucks, cargo vans and towing equipped pickup trucks are available for daily, weekly or monthly rental.