Find and compare great deals on Payless rental cars in Chicago
Same drop-off
Payless car rental deals in Chicago, Illinois
Find your perfect rental car on momondo
Choose your travel dates to find the best prices
Small
Medium
Large
SUV
Van
Luxury
Small Cars
$49 - $173
All Car Types
$68 - $135
The best time to rent a Small car from Payless in Chicago, Illinois is in May when prices are $49 per day on average. $49 per day is 46% lower than the $92 average yearly price for a Payless Small rental in Chicago. While May may be the cheapest month to rent a Small car from Payless in Chicago, December is the most expensive. However, you may still be able to find great deals in December on Small rental vehicles from Payless depending on what day you book.
The best time to rent a Medium car from Payless in Chicago, Illinois is in November when prices are $41 per day on average. $41 per day is 45% lower than the $75 average yearly price for a Payless Medium rental in Chicago. While November may be the cheapest month to rent a Medium car from Payless in Chicago, December is the most expensive. However, you may still be able to find great deals in December on Medium rental vehicles from Payless depending on what day you book.
The best time to rent a Large car from Payless in Chicago, Illinois is in December when prices are $71 per day on average. $71 per day is 54% lower than the $154 average yearly price for a Payless Large rental in Chicago. While December may be the cheapest month to rent a Large car from Payless in Chicago, April is the most expensive. However, you may still be able to find great deals in April on Large rental vehicles from Payless depending on what day you book.
The best time to rent a SUV car from Payless in Chicago, Illinois is in November when prices are $41 per day on average. $41 per day is 49% lower than the $81 average yearly price for a Payless SUV rental in Chicago. While November may be the cheapest month to rent a SUV car from Payless in Chicago, September is the most expensive. However, you may still be able to find great deals in September on SUV rental vehicles from Payless depending on what day you book.
The best time to rent a Van car from Payless in Chicago, Illinois is in February when prices are $59 per day on average. $59 per day is 55% lower than the $131 average yearly price for a Payless Van rental in Chicago. While February may be the cheapest month to rent a Van car from Payless in Chicago, January is the most expensive. However, you may still be able to find great deals in January on Van rental vehicles from Payless depending on what day you book.
The best time to rent a Luxury car from Payless in Chicago, Illinois is in October when prices are $70 per day on average. $70 per day is 42% lower than the $121 average yearly price for a Payless Luxury rental in Chicago. While October may be the cheapest month to rent a Luxury car from Payless in Chicago, May is the most expensive. However, you may still be able to find great deals in May on Luxury rental vehicles from Payless depending on what day you book.
I wasn't able to rent from them, I had made a mistake in the past with one of its sister companies, and instead of (me) correcting the problem I have been banned from ever using them.
2.0
Poor|Sep 2023
They could have more counters open and have a prebook time in advance at least 30 min… been waiting for an hour and a half to get the car and after I just gave up waiting and took a taxi. So if you can’t provide your clients with the car at the moment then give people instructions how long it’s going to take.
2.0
Poor|Sep 2023
They didn’t give me my full deposit back
8.0
Very good|Jul 2023
Ummm They did not rip me off on full tank Fuel this time … like they did in Boston
2.0
Poor|Jun 2023
Customer service was terrible! Had attitude problems! Didn’t even get the rental car! I deserve a refund!
6.0
Okay|Jun 2023
Great car. Too May extra extra charges just for extending the rental for a few days.
1 out of 14
View Payless Locations in Chicago
Information about Payless car rentals in Chicago
How much will a Payless rental car in Chicago cost in October?
Renting a car in Chicago from Payless during October will cost an average of $90 per day. However, some of our users found prices last October as low as $31 per day from Payless, so you may be able to find similar prices this year. If you’re looking to rent a car in Chicago for one week, $633 is the average cost for a rental from Payless.
Does Payless have a location at Chicago Midway Airport?
Payless has 1 location at Chicago Midway Airport. You will find Payless located at 5401 West 47th Street.
What is the most popular car to rent from Payless while in Chicago in October?
The most popular type of car to rent from Payless in Chicago during October are Luxury rentals. You can expect to pay around $103 per day for Luxury rentals in October, though some of our users found prices for as low as $66 per day.
What is the cheapest type of car to rent from Payless in Chicago?
For $81/day on average, a Intermediate is the cheapest type of car to rent from Payless in Chicago (31% cheaper than the most expensive Payless rental car). In the past year, 20% of momondo users who chose to rent from Payless while in Chicago rented a Intermediate in order to save money. Keep in mind that Payless also has other types of car rentals available based on your travel needs.
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 121 as of September 2026.
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.