Cheap Car Rentals in Near South Side, Chicago from $40
This price is the cheapest per day rate found by a Cheapflights user in the last 48 hours by searching for a car rental in Near South Side with a pick-up date of 6/27 and drop-off date of 7/5. Fares are subject to change and may not be available at all agencies or on all dates of rental.
Near South Side, Chicago car rentals in 2026
Get helpful information to start your search for the perfect car rental in Near South Side. The average price data is based on the last 12 months and was last updated on June 11, 2026.
Most popular company | Sixt |
|---|---|
Most common car type | SUV |
Average price per day | $109 |
Cheapest price per day | $40 |
Best Near South Side, Chicago car rental deals
Browse through the best deals we’ve found on Near South Side car rental deals at this time. Deals are sourced from providers and were last updated on June 11, 2026.
Cheapflights insights for Near South Side car rentals
Get relevant, data-driven information to help you rent a car in Near South Side, including pricing trends, ideal booking times, and more.
How far in advance should I rent a car in Near South Side?
To get the best deal on a rental car in Near South Side, book about 63 days before your trip. At that point, average daily prices are around $31, which is about 35% cheaper than the typical rate.
What is the best car rental company in Near South Side?
Based on Cheapflights user feedback, the highest rated car rental company in Near South Side is Enterprise Rent-A-Car (rated 7.8/10 with 7 reviews). Sixt (rated 7.2/10 with 12 reviews) is also highly rated by our users.
What is the cheapest month to rent a car in Near South Side?
At Near South Side, the best time to rent a car is in January, with an average daily rate of just $35. Conversely, March is the priciest month, averaging $63 per day. Below youll find the monthly average rental prices. Note that costs can fluctuate depending on availability, booking time, and vehicle type.|1#In Near South Side, the best time to rent a car is in January, with an average daily rate of just $35. Conversely, March is the priciest month, averaging $63 per day. Below youll find the monthly average rental prices. Note that costs can fluctuate depending on availability, booking time, and vehicle type.
January
$35
February
$43
March
$63
April
$58
May
$56
June
$58
July
$56
August
$39
September
$39
October
$41
November
$42
December
$39
Which car rental company has the most locations in Near South Side?
In Near South Side, Enterprise Rent-A-Car, Avis, and Sixt have 2 locations, more than any other rental company in the area.
Top rental agencies in Near South Side, Chicago
Explore the most popular car rental suppliers in Near South Side, including their locations and customer reviews, to make the best choice for your next trip.
Enterprise Rent-A-Car
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View Enterprise Rent-A-Car Locations in Near South Side
Sixt
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View Sixt Locations in Near South Side
Avis
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View Avis Locations in Near South Side
Hertz
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View Hertz Locations in Near South Side
Budget
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View Budget Locations in Near South Side
Near South Side Car rental FAQs
Find answers to frequently asked questions about car rentals in Near South Side, including policies, requirements, and more. FAQs were last updated on June 11, 2026.
Can I rent a car for a month at Near South Side?
Typically how long you can rent a car for depends on the inventory of the supplier. For Near South Side however, it is certainly possible to rent a car for an entire month.
What is the cheapest rental car in Near South Side, Chicago?
For $53 per day on average, the Class Special Car is the cheapest car rental in Near South Side, Chicago. Renting a Class Special Car is 38% cheaper than the average cost of other car rentals in Near South Side.
How much is a rental car in Near South Side, Chicago?
$53 per day, on average, is how much a rental car in Near South Side, Chicago costs. However, our users have found rentals for as low as $54 per day.