Small Cars | $81 - $184 | |
|---|---|---|
All Car Types | $99 - $154 |
The best time to rent a Small car from Enterprise Rent-A-Car in Chicago, Illinois is in September when prices are $81 per day on average. $81 per day is 24% lower than the $106 average yearly price for a Enterprise Rent-A-Car Small rental in Chicago. While September may be the cheapest month to rent a Small car from Enterprise Rent-A-Car in Chicago, January is the most expensive. However, you may still be able to find great deals in January 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 $55 per day on average. $55 per day is 47% lower than the $105 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, August is the most expensive. However, you may still be able to find great deals in August 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 September when prices are $96 per day on average. $96 per day is 25% lower than the $128 average yearly price for a Enterprise Rent-A-Car Large rental in Chicago. While September may be the cheapest month to rent a Large car from Enterprise Rent-A-Car in Chicago, January is the most expensive. However, you may still be able to find great deals in January 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 February when prices are $78 per day on average. $78 per day is 31% lower than the $113 average yearly price for a Enterprise Rent-A-Car SUV rental in Chicago. While February may be the cheapest month to rent a SUV 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 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 September when prices are $97 per day on average. $97 per day is 22% lower than the $125 average yearly price for a Enterprise Rent-A-Car Van rental in Chicago. While September may be the cheapest month to rent a Van car from Enterprise Rent-A-Car in Chicago, January is the most expensive. However, you may still be able to find great deals in January 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 March when prices are $88 per day on average. $88 per day is 37% lower than the $140 average yearly price for a Enterprise Rent-A-Car Luxury rental in Chicago. While March may be the cheapest month to rent a Luxury car from Enterprise Rent-A-Car in Chicago, December is the most expensive. However, you may still be able to find great deals in December 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 April when prices are $72 per day on average. $72 per day is 50% lower than the $145 average yearly price for a Enterprise Rent-A-Car Convertible rental in Chicago. While April 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.
$51/day
12 Nov - 12 Dec$51/day
3 Nov - 3 DecEnterprise Rent-A-Car
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At the moment, Enterprise Rent-A-Car has 1 location at Chicago Midway Airport:
5150 W 55th St.
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.
Consider Intermediate rentals from Enterprise Rent-A-Car if you need a car rental in Chicago during November. When renting Intermediate cars in November, you can expect prices to be an average of $80 per day and as low as $49 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.
If you’re looking to save money on your rental car from Enterprise Rent-A-Car, then consider renting a Luxury, the cheapest type of car the rental company has available in Chicago. Renting a Luxury from Enterprise Rent-A-Car costs $107 per day on average, which is 58% cheaper than their most expensive car. In the past year, 7% of our users opted to rent a Luxury from Enterprise Rent-A-Car in order to save money on their trip to 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, 36% 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.
Prices for cars in Chicago refresh daily.
The number of operators available for cars in Chicago is 125 as of October 2025.
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.
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.