Find and compare great deals on Enterprise Rent-A-Car rental cars in Chicago
Same drop-off
Driver's age: 25-65
Enterprise Rent-A-Car car rental deals in Chicago, Illinois
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Choose your travel dates to find the best prices
Small Cars
C$ 118 - C$ 269
All Car Types
C$ 126 - C$ 255
The best time to rent a Small car from Enterprise Rent-A-Car in Chicago, Illinois is in March when prices are C$ 118 per day on average. C$ 118 per day is 27% lower than the C$ 162 average yearly price for a Enterprise Rent-A-Car Small rental in Chicago. While March may be the cheapest month to rent a Small 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 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 September when prices are C$ 78 per day on average. C$ 78 per day is 51% lower than the C$ 158 average yearly price for a Enterprise Rent-A-Car Medium rental in Chicago. While September 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 October when prices are C$ 120 per day on average. C$ 120 per day is 40% lower than the C$ 202 average yearly price for a Enterprise Rent-A-Car Large rental in Chicago. While October may be the cheapest month to rent a Large car from Enterprise Rent-A-Car in Chicago, June is the most expensive. However, you may still be able to find great deals in June 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 November when prices are C$ 60 per day on average. C$ 60 per day is 64% lower than the C$ 168 average yearly price for a Enterprise Rent-A-Car SUV rental in Chicago. While November may be the cheapest month to rent a SUV 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 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 C$ 104 per day on average. C$ 104 per day is 46% lower than the C$ 193 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, November is the most expensive. However, you may still be able to find great deals in November on Van 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
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?
There is 1 location at Chicago Midway Airport. The address for this Enterprise Rent-A-Car car rental center is 5150 W 55th St.
Does Enterprise Rent-A-Car offer free car rental cancellation in Chicago?
Yes, you can cancel your Enterprise Rent-A-Car rental car reservation in Chicago free of charge. However, cancelling your car rental right before your scheduled pick-up date could result in a fee. Be sure to call Enterprise Rent-A-Car and ask about specific cancellation policies. You can view a list of phone numbers under the Locations tab by clicking here.
What is the most popular car to rent from Enterprise Rent-A-Car while in Chicago in January?
The most popular type of car to rent from Enterprise Rent-A-Car in Chicago during January are Compact rentals. You can expect to pay around C$ 116 per day for Compact rentals in January, though some of our users found prices for as low as C$ 104 per day.
What is the cheapest type of car to rent from Enterprise Rent-A-Car in Chicago?
The cheapest type of car Enterprise Rent-A-Car has to offer in Chicago is the Compact at C$ 116 per day on average. C$ 116 per day is 10% cheaper than the most expensive car available at Enterprise Rent-A-Car, so you end up saving some money by choosing a more affordable option. 40% of momondo users who rented a car in Chicago from Enterprise Rent-A-Car chose the Compact, often because of the cost savings.
How many Enterprise Rent-A-Car car rental locations are there in Chicago?
10255 W Zemke Blvd is the most popular Enterprise Rent-A-Car car rental location out of the 27 locations they have in Chicago. According to our user data over the past 12 months, 35% of those who opted to rent a car from Enterprise Rent-A-Car did so at the 10255 W Zemke Blvd location.
When did momondo last update prices for cars in Chicago?
Prices for cars in Chicago were last updated today.
How many operators does momondo search for cars in Chicago?
There are 125 operators available for cars in Chicago as of December 2025.
How old do you have to be to hire a car in Chicago?
The minimum age for drivers varies by country, including Chicago. In many EU countries drivers must be 18 years old. As a rule, you’ll need to be 21 to hire a car abroad, and a young driver surcharge may be applied if you are under 25. We recommend reading through the policy of your chosen rental company before booking.
What documentation or ID do you need to rent a car in Chicago?
When renting a car in Chicago, all drivers must present a full valid driving license. An International Driving Permit is required if the driving license is written in a language different to that of the country of rental and may be necessary to avoid the risk of potential fines. If you are renting abroad, you may also need to provide proof of return travel and accommodation information during your stay. We always recommend checking with the individual rental company you are booking with.
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