Enterprise
Truck Rentals

Pickup Truck Rental in Chicago

If you need to move furniture or haul supplies, renting a pickup truck through Enterprise will make the process much easier. We have trucks of various sizes to best suit your needs. Reserve a truck online for our lowest rates. 

Explore Truck Rental Options

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FAQs for Renting Trucks in Chicago

Yes, all of our pickup trucks can be rented one way. This option is great if you are moving small items a few hours away or taking a cross-state road trip with rugged terrain. A drop charge may apply for one-way rentals, which will be disclosed at the time of reservation. 

Trucks are not available by the hour, but Enterprise does rent out trucks by the day. This gives you the flexibility to use the truck for several hours or a full day. We offer great rates and our easy rental process will get you on the road quickly. 

Although pickup trucks from our Enterprise Rent-A-Car fleet cannot be used to tow, you can go through Enterprise Truck Rental to do so. The Enterprise Truck division offers 3/4 ton pickup trucks and 1-ton pickup trucks that can be used to tow boats, campers, and more. 

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