Find and compare great deals on Enterprise Rent-A-Car rental cars in Chicago
Same drop-off
Enterprise Rent-A-Car car rental deals in Chicago, Illinois
Find your perfect rental car on momondo
Choose your travel dates to find the best prices
Small Cars
$63 - $147
All Car Types
$91 - $136
The best time to rent a Small car from Enterprise Rent-A-Car in Chicago, Illinois is in May when prices are $63 per day on average. $63 per day is 34% lower than the $96 average yearly price for a Enterprise Rent-A-Car Small rental in Chicago. While May may be the cheapest month to rent a Small car from Enterprise Rent-A-Car in Chicago, March is the most expensive. However, you may still be able to find great deals in March on Small rental vehicles from Enterprise Rent-A-Car depending on what day you book.
The best time to rent a Medium car from Enterprise Rent-A-Car in Chicago, Illinois is in June when prices are $58 per day on average. $58 per day is 42% lower than the $100 average yearly price for a Enterprise Rent-A-Car Medium rental in Chicago. While June may be the cheapest month to rent a Medium car from Enterprise Rent-A-Car in Chicago, April is the most expensive. However, you may still be able to find great deals in April on Medium rental vehicles from Enterprise Rent-A-Car depending on what day you book.
The best time to rent a Large car from Enterprise Rent-A-Car in Chicago, Illinois is in June when prices are $87 per day on average. $87 per day is 25% lower than the $115 average yearly price for a Enterprise Rent-A-Car Large rental in Chicago. While June may be the cheapest month to rent a Large car from Enterprise Rent-A-Car in Chicago, February is the most expensive. However, you may still be able to find great deals in February on Large rental vehicles from Enterprise Rent-A-Car depending on what day you book.
The best time to rent a SUV car from Enterprise Rent-A-Car in Chicago, Illinois is in October when prices are $64 per day on average. $64 per day is 46% lower than the $118 average yearly price for a Enterprise Rent-A-Car SUV rental in Chicago. While October may be the cheapest month to rent a SUV car from Enterprise Rent-A-Car in Chicago, July is the most expensive. However, you may still be able to find great deals in July on SUV rental vehicles from Enterprise Rent-A-Car depending on what day you book.
The best time to rent a Van car from Enterprise Rent-A-Car in Chicago, Illinois is in June when prices are $75 per day on average. $75 per day is 32% lower than the $110 average yearly price for a Enterprise Rent-A-Car Van rental in Chicago. While June may be the cheapest month to rent a Van car from Enterprise Rent-A-Car in Chicago, July is the most expensive. However, you may still be able to find great deals in July on Van rental vehicles from Enterprise Rent-A-Car depending on what day you book.
The best time to rent a Luxury car from Enterprise Rent-A-Car in Chicago, Illinois is in July when prices are $69 per day on average. $69 per day is 47% lower than the $129 average yearly price for a Enterprise Rent-A-Car Luxury rental in Chicago. While July may be the cheapest month to rent a Luxury car from Enterprise Rent-A-Car in Chicago, August is the most expensive. However, you may still be able to find great deals in August on Luxury rental vehicles from Enterprise Rent-A-Car depending on what day you book.
The best time to rent a Convertible car from Enterprise Rent-A-Car in Chicago, Illinois is in March when prices are $73 per day on average. $73 per day is 54% lower than the $158 average yearly price for a Enterprise Rent-A-Car Convertible rental in Chicago. While March may be the cheapest month to rent a Convertible car from Enterprise Rent-A-Car in Chicago, August is the most expensive. However, you may still be able to find great deals in August on Convertible rental vehicles from Enterprise Rent-A-Car depending on what day you book.
Professional staff! Super clean car! Hate driving in chicago
10.0
Wonderful|Aug 2023
Location was a bit confusing to find but when I did the customer service was friendly. Had a free upgrade. Then drop off at the airport was a breeze took less than a minute.
10.0
Wonderful|Aug 2023
Representatives were extremely kind and professional.
10.0
Wonderful|Feb 2023
Guys working at the enterprise were great to deal with.
10.0
Wonderful|Feb 2023
Pleasant, helpful, and attentive. I will rent with them again.
10.0
Wonderful|Dec 2022
Great customer service
1 out of 19
View Enterprise Rent-A-Car Locations in Chicago
Information about Enterprise Rent-A-Car car rentals in Chicago
Does Enterprise Rent-A-Car have a location at Chicago Midway Airport?
At the moment, Enterprise Rent-A-Car has 1 location at Chicago Midway Airport: 5150 W 55th St.
Does Enterprise Rent-A-Car offer free car rental cancellation in Chicago?
There are free rental car cancellations available from Enterprise Rent-A-Car in Chicago. Keep in mind that there might be a cancellation fee if you cancel your rental car last-minute. Click here to find a list of phone numbers under the Locations tab if you’d like to learn more about Enterprise Rent-A-Car cancellation policies.
What is the most popular car to rent from Enterprise Rent-A-Car while in Chicago in January?
Consider Intermediate rentals from Enterprise Rent-A-Car if you need a car rental in Chicago during January. When renting Intermediate cars in January, you can expect prices to be an average of $98 per day and as low as $47 per day. Keep in mind that there are also other types of rental cars available from Enterprise Rent-A-Car—Intermediate vehicles just happen to be the most popular amongst our users during this time of year.
What is the cheapest type of car to rent from Enterprise Rent-A-Car in Chicago?
If you’re looking to save money on your rental car from Enterprise Rent-A-Car, then consider renting a Compact, the cheapest type of car the rental company has available in Chicago. Renting a Compact from Enterprise Rent-A-Car costs $111 per day on average, which is 52% cheaper than their most expensive car. In the past year, 15% of our users opted to rent a Compact from Enterprise Rent-A-Car in order to save money on their trip to Chicago.
How many Enterprise Rent-A-Car car rental locations are there in Chicago?
There are 27 car rental locations in Chicago that Enterprise Rent-A-Car owns. Their 10255 W Zemke Blvd, Chicago location happens to be the most popular amongst our users. In the last 12 months, 35% of the users who rented a car from Enterprise Rent-A-Car in Chicago chose to pick up their rental at 10255 W Zemke Blvd.
When did momondo last update prices for cars in Chicago?
Prices for cars in Chicago refresh daily.
How many operators does momondo search for cars in Chicago?
The number of operators available for cars in Chicago is 125 as of December 2025.
How old do you have to be to hire a car in Chicago?
Among different countries, including Chicago, the minimum age for drivers varies. In numerous EU countries, drivers must be 18 years old. To hire a car overseas, you'll generally need to be at least 21, and if you're under 25, a young driver surcharge may be imposed. It's recommended that you review the policy of the rental company you're considering before booking.
What documentation or ID do you need to rent a car in Chicago?
To rent a car in Chicago, all drivers must have a valid full driving license. If the license is written in a language other than the language of the country of rental, an International Driving Permit may be required to avoid the risk of potential fines. If you're renting a car abroad, you may also need to provide proof of return travel and accommodation information during your stay. We recommend that you verify with the specific rental company you're booking with.
An easier way to manage your Chicago trip
We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
This site uses cookies and other tracking technologies for essential, functional, analytical, and advertising purposes. By using the site, you agree to our Terms & Conditions and our Privacy Policy.
For more information about how we process your information, please see our Privacy Policy.
We value your privacy
momondo and its partners wish to use cookies or similar technologies to store and/or access information on and about your device and process personal data such as your IP address, device identifiers etc., in order to improve your experience on the site, to analyze navigation, to offer and measure personalized advertising, and to facilitate sharing on social networks. We also allow the use of third-party cookies (including those from our advertising partners) on our sites.
By clicking 'Accept', you consent to your data being processed by 0 vendors on this web site for the purposes described in this notice. You can review the vendors and their individual processing purposes on the .
To review individual processing purposes and cookie categories, please click ’Select individual purposes’. You can review your choices and withdraw your consent at any time by clicking the ’Privacy Preferences’ link in the page side navigation.