chicago skyline

Chicago Car Rental

Chicago rises along Lake Michigan with a skyline shaped by architectural icons, a food scene that never stops evolving, and neighborhoods that each feel like their own small city. With a rental car, you can easily move from the lakefront to music filled corners of the West Side, wander historic districts, or head out to the suburbs and shoreline towns that surround the city. Chicago rewards exploring at your own pace, and having a car makes it easy to see how much variety fits within its wide reach.

Enterprise Car Rental Locations in Chicago

Enterprise Rent A Car offers convenient pickup options throughout the Chicago area, including locations at O’Hare International Airport and Midway International Airport. Neighborhood branches across the city and surrounding suburbs make it simple to rent a car whether you are arriving by plane or already in town. You can choose a vehicle for a day, a weekend, or a longer stay with plenty of flexible options nearby.

Deals

Car Rental Deals

Find low rates & seasonal offers to get more out of your trip. Whether you’re booking last minute or planning ahead, Enterprise makes it easy to find a deal that fits your budget.

Earn Free Days

Enterprise Plus Rewards

Join Enterprise Plus® and start earning points with every rental. Members enjoy free rentals, faster reservations, and exclusive benefits that make each trip even more rewarding.

Manage On The Go

Save Time With The Enterprise App

Manage reservations, choose your car, and check in before you arrive with the Enterprise car rental app. Spend less time at the counter and more time on the road. Available in the App Store & Google Play.

Things to do in Chicago

Chicago offers a wide mix of attractions, from lakefront parks and world class museums to historic neighborhoods and iconic sports venues. With a rental car, it is easy to move between the city’s top sights, explore along the waterfront, and add nearby districts or day trips to your itinerary. These highlights help you make the most of your time in Chicago at your own pace.

Millennium Park is one of Chicago’s most popular gathering spots, known for public art, gardens, and open space in the middle of the city. Cloud Gate, often called “The Bean,” is a must see for first time visitors and makes a perfect starting point for exploring the lakefront and nearby museums.

The Art Institute of Chicago holds one of the largest and most diverse art collections in the country, ranging from ancient artifacts to modern masterpieces. It is easy to spend a few hours here before walking across the street to explore Grant Park or continue on to the lakefront.

Navy Pier combines waterfront views, family friendly attractions, restaurants, and boat tours that offer a fresh perspective on the city skyline. With a rental car, you can easily pair your visit with stops at nearby beaches or neighborhoods along the shoreline.

The Chicago Riverwalk offers a scenic path lined with restaurants, public art, and spots to relax by the water. It is a great place for a leisurely walk, and having a car makes it simple to continue exploring riverfront neighborhoods or take an architecture cruise nearby.

The Magnificent Mile is Chicago’s most famous stretch for shopping, dining, and high‑rise views. It is an easy area to navigate by car, letting you explore nearby attractions like the John Hancock Center or make quick trips to neighborhoods just north of downtown.

Lincoln Park Zoo is one of the oldest free zoos in the country and sits within a large park that includes walking paths, gardens, and lakefront access. Visitors often pair the zoo with a stop at North Avenue Beach or a drive through historic Lincoln Park.

The Museum of Science and Industry offers hands‑on exhibits, immersive experiences, and some of the most memorable museum displays in Chicago. It is located in the Hyde Park neighborhood, and having a rental car makes the trip quick and convenient.

Wrigley Field blends classic ballpark charm with the energy of the surrounding Wrigleyville neighborhood. Even if you are not catching a game, the area offers restaurants, shops, and easy access by car to other North Side neighborhoods.

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.

Popular Rental Cars in Chicago

Enterprise makes it easy to choose the right vehicle for your plans in Chicago. Pick a compact car for navigating downtown traffic and tight parking garages, or choose an SUV if you are heading to lakefront parks, suburban attractions, or weekend escapes beyond the city. Planning a group outing to a ballgame or museum? A spacious van keeps everyone comfortable. If you need a truck for moving or work projects, or want a premium car for a night out along the Magnificent Mile, we have options to match your trip.

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.

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.

luxury car rental

Luxury Cars

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

friendly enterprise employee hands over rental car keys

One Way Car Rentals

Go One-Way, Your Way

Skip the round trip and return your rental car at a different branch. One-way rentals offer the flexibility to keep your travel plans moving forward, whether you’re heading out on a road trip, relocating, or catching a flight from another city.

Travel Tips for Driving in Chicago

Most Chicago residential streets have a 30 mph speed limit unless otherwise posted. Major arterials may increase to 35 or 40 mph, and expressways such as I‑90, I‑94, and I‑290 generally range from 55 to 60 mph as you approach and leave the city center. Speed limits vary frequently, so it is important to follow posted signs.

Chicago offers a mix of metered street parking, garages, and private lots. Street meters vary by neighborhood and typically cost between 2 and 6.50 dollars per hour. Downtown areas like the Loop and River North offer many garages, while neighborhoods outside the core may provide easier access to street parking with posted rules.

Many residential streets require a valid Chicago Residential Zone Parking permit, which is tied to a resident’s city sticker and enforced during posted hours. Visitor passes are available for short stays, and violations can result in ticketing or towing. Because signs vary by block, always check curbside restrictions before parking.

Weekday rush hours between 7 and 9 a.m. and 4 and 6 p.m. are the most congested, especially on expressways leading into and out of downtown. Mid‑mornings, early afternoons, and later evenings often provide smoother travel. Winter weather can slow traffic significantly, while summer brings heavy activity near lakefront parks and festival areas.

From O’Hare International Airport, the Kennedy Expressway (I 90) provides direct access to downtown and is the most common driving route. From Midway International Airport, traffic flows into the city via Cicero Avenue and I 55, which offers a straightforward path toward the Loop. Both routes can become congested at peak times, so planning your trip outside rush hour can shorten travel times.

Yes, several major expressways around Chicago operate with tolls, including sections of I 90, I 294, and I 355. Tolls are collected electronically through I Pass or E ZPass, though pay by plate billing is available if you do not have a transponder. If your plans include suburban travel, checking your route ahead of time helps avoid unexpected toll segments.

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Ready To Hit The Road?

Choose the right rental for your trip and get on your way with Enterprise.

Enterprise Car Sales - Chicago

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.

Exotic Car Rental

Explore Chicago in luxury with exotic sports cars, sedans and SUVS. We have the area's largest selection of exotic and premium vehicles available for rent.

Enterprise Truck Rental - Chicago

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