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 Chicago with a pick-up date of 22/5 and drop-off date of 26/5. Fares are subject to change and may not be available at all agencies or on all dates of rental. Click the price to replicate the search for this deal.
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Driver's age: 25-65
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Jeep car rentals in 2026
Get helpful information to start your search for the perfect Jeep rental in Chicago. The average price data is based on the last 7 days and was last updated on 14 May 2026.
When is the cheapest time to rent a Jeep in Chicago?
Find the cheapest period to rent a Jeep in Chicago so you can save money on your upcoming trip. The monthly average prices are based on past data over the last year and was last updated on 14 May 2026.
January
C$ 52
February
C$ 46
March
C$ 54
April
C$ 65
May
C$ 79
June
C$ 94
July
C$ 117
August
C$ 106
September
C$ 82
October
C$ 83
November
C$ 83
December
C$ 75
February is the cheapest time of the year to rent a Jeep in Chicago, according to our data. July tends to be the most expensive time of year to rent a Jeep. The cheapest prices for each month are shown above, but prices will vary based on availability, how far out you book your Jeep rental car, and what rental agency you book with.
Popular Jeep models to rent in Chicago
Explore the most popular Jeep models available for rent in Chicago and choose the one that suits your needs. The price data is sourced from 8 car rental companies and was last updated on 14 May 2026.
There are 8 companies in Chicago that offer Jeep rental cars. The Wrangler Unlimited is the cheapest Jeep car model users can rent (cheapest price last found: C$ 61/day). Compare prices for 2 models currently offered from Chicago rental providers.
Check out some of the most affordable deals on Jeep rentals in Chicago. Prices were updated on 14 May 2026.
These are the cheapest deals we’ve found for Jeep rental cars in Chicago in the past 7 days. Use our Price Alert feature (click the bell icon below) to get the latest updates on great Jeep deals.
Jeep CompassC$ 90/day
4
M
A/C
Jeep CherokeeC$ 96/day
5
M
A/C
Jeep Grand CherokeeC$ 99/day
5
M
A/C
Compare available Jeep models for rent in Chicago
Compare prices on various Jeep models in Chicago and find the perfect fit for your trip. Price data is based on averages over the last year and was last updated on 14 May 2026.
Grand Cherokee L
Compass
Cherokee
Grand Cherokee
Wrangler Unlimited
Wrangler
Renegade
Patriot
Grand Cherokee L Cars
C$ 97 - C$ 169
All Car Models
C$ 72 - C$ 118
To rent a Jeep Grand Cherokee L in Chicago, Illinois, you would pay an average price of C$ 171/day. March is the cheapest month to rent a Jeep Grand Cherokee L in Chicago (~C$ 133/day), while the most expensive month to rent the Jeep Grand Cherokee L is July (~C$ 232/day).
In fact, March is about 22% cheaper than prices during the rest of the year to book a Jeep Grand Cherokee L rental for a trip to Chicago. When compared to other Jeep models available to rent in Chicago, renting a Grand Cherokee L is 30% more expensive.
Please note that average prices are based on historical data and can vary depending on how early you book, availability based on your travel dates, and vehicle popularity.
Here are the best Jeep Grand Cherokee L rental prices found by Cheapflights users in the past 7 days:
To rent a Jeep Compass in Chicago, Illinois, you would pay an average price of C$ 114/day. January is the cheapest month to rent a Jeep Compass in Chicago (~C$ 47/day), while the most expensive month to rent the Jeep Compass is July (~C$ 151/day).
In fact, January is about 59% cheaper than prices during the rest of the year to book a Jeep Compass rental for a trip to Chicago. When compared to other Jeep models available to rent in Chicago, renting a Compass saves you 6% in costs.
Please note that average prices are based on historical data and can vary depending on how early you book, availability based on your travel dates, and vehicle popularity.
Here are the best Jeep Compass rental prices found by Cheapflights users in the past 7 days:
To rent a Jeep Cherokee in Chicago, Illinois, you would pay an average price of C$ 90/day. February is the cheapest month to rent a Jeep Cherokee in Chicago (~C$ 44/day), while the most expensive month to rent the Jeep Cherokee is December (~C$ 137/day).
In fact, February is about 51% cheaper than prices during the rest of the year to book a Jeep Cherokee rental for a trip to Chicago. When compared to other Jeep models available to rent in Chicago, renting a Cherokee saves you 27% in costs.
Please note that average prices are based on historical data and can vary depending on how early you book, availability based on your travel dates, and vehicle popularity.
Here are the best Jeep Cherokee rental prices found by Cheapflights users in the past 7 days:
To rent a Jeep Grand Cherokee in Chicago, Illinois, you would pay an average price of C$ 192/day. October is the cheapest month to rent a Jeep Grand Cherokee in Chicago (~C$ 119/day), while the most expensive month to rent the Jeep Grand Cherokee is January (~C$ 296/day).
In fact, October is about 38% cheaper than prices during the rest of the year to book a Jeep Grand Cherokee rental for a trip to Chicago. When compared to other Jeep models available to rent in Chicago, renting a Grand Cherokee is 37% more expensive.
Please note that average prices are based on historical data and can vary depending on how early you book, availability based on your travel dates, and vehicle popularity.
Here are the best Jeep Grand Cherokee rental prices found by Cheapflights users in the past 7 days:
To rent a Jeep Wrangler Unlimited in Chicago, Illinois, you would pay an average price of C$ 79/day. January is the cheapest month to rent a Jeep Wrangler Unlimited in Chicago (~C$ 52/day), while the most expensive month to rent the Jeep Wrangler Unlimited is July (~C$ 112/day).
In fact, January is about 34% cheaper than prices during the rest of the year to book a Jeep Wrangler Unlimited rental for a trip to Chicago. When compared to other Jeep models available to rent in Chicago, renting a Wrangler Unlimited saves you 36% in costs.
Please note that average prices are based on historical data and can vary depending on how early you book, availability based on your travel dates, and vehicle popularity.
Here are the best Jeep Wrangler Unlimited rental prices found by Cheapflights users in the past 7 days:
To rent a Jeep Wrangler in Chicago, Illinois, you would pay an average price of C$ 106/day. February is the cheapest month to rent a Jeep Wrangler in Chicago (~C$ 77/day), while the most expensive month to rent the Jeep Wrangler is July (~C$ 142/day).
In fact, February is about 28% cheaper than prices during the rest of the year to book a Jeep Wrangler rental for a trip to Chicago. When compared to other Jeep models available to rent in Chicago, renting a Wrangler saves you 13% in costs.
Please note that average prices are based on historical data and can vary depending on how early you book, availability based on your travel dates, and vehicle popularity.
Here are the best Jeep Wrangler rental prices found by Cheapflights users in the past 7 days:
To rent a Jeep Renegade in Chicago, Illinois, you would pay an average price of C$ 114/day. November is the cheapest month to rent a Jeep Renegade in Chicago (~C$ 93/day), while the most expensive month to rent the Jeep Renegade is June (~C$ 130/day).
In fact, November is about 18% cheaper than prices during the rest of the year to book a Jeep Renegade rental for a trip to Chicago. When compared to other Jeep models available to rent in Chicago, renting a Renegade saves you 6% in costs.
Please note that average prices are based on historical data and can vary depending on how early you book, availability based on your travel dates, and vehicle popularity.
Here are the best Jeep Renegade rental prices found by Cheapflights users in the past 7 days:
To rent a Jeep Patriot in Chicago, Illinois, you would pay an average price of C$ 105/day. February is the cheapest month to rent a Jeep Patriot in Chicago (~C$ 64/day), while the most expensive month to rent the Jeep Patriot is January (~C$ 138/day).
In fact, February is about 39% cheaper than prices during the rest of the year to book a Jeep Patriot rental for a trip to Chicago. When compared to other Jeep models available to rent in Chicago, renting a Patriot saves you 14% in costs.
Please note that average prices are based on historical data and can vary depending on how early you book, availability based on your travel dates, and vehicle popularity.
Jeep Grand Cherokee LC$ 120/day
5
M
A/C
Jeep Grand Cherokee LC$ 122/day
5
M
A/C
Jeep Grand Cherokee LC$ 126/day
5
M
A/C
Jeep rental agencies in Chicago
Explore the leading car rental agencies in Chicago offering Jeep rentals.There are currently 8 different car rental companies in Chicago that have a Jeep available to rent. Reviews for these rental agencies were last updated on 14 May 2026.
Rent a Jeep from one of these top rental car agencies serving Chicago, such as Hertz, Budget and Dollar. Read user reviews and find contact information for each rental agency.
They did not have the car and never notified me. Late the night before i called and discovered this. Calling hertz was a nightmare. Kept getting shuttled to sales.
10.0
Wonderful|May 2023
Great customer service the lady was very patient and polite. Thanks again for your service.
4.0
Mediocre|May 2023
Frustrating pick up. Had a Tesla reserved for me but the battery was only 22%. Spent another 45 minutes trying to get a different car. They charged an additional $15 per day for changing cars.
4.0
Mediocre|May 2023
I had to change my reservation because I did it with a virtual card thru my affirm account and didn’t have a physical card. I I was informed that before the transaction I would have maybe not done it that way. A waste of time and was on hold to change the reservation with hertz for an 45 minutes. The rep at the location couldn’t update the credit card information so I had to call. Just a waste of time and energy!
Poor pick up experience. They seemed to let the line grow to an unacceptable length deliberately before attending to customers. But the gentleman was friendly when I eventually got there and we got a brand new car
2.0
Poor|Jul 2023
Canceled the reservation: when I showed up there was a line of more than 50 people and only two agents working the counter. Took an uber instead.
6.0
Okay|Jul 2023
Staff friendly and helpful but needed more staff to moved things along quicker
4.0
Mediocre|Jul 2023
Staff were extremely polite and accommodating and this is the one redeeming factor. It took about an hour waiting in line to reach the budget counter. Seemed like everything went fine until we reached the garage and found out we were given a Ford Runner with terrible mileage for hundreds of miles of turnpike driving. Representative in the garage tried to help us out and moved us into a Chevy Malibu. Unfortunately the car was dirty (obvious trash left in car), but we were willing to deal since we were already severely delayed. But then we reached the garage gate to checkout and found out from the attendant that one extra feature we asked for; an Ezpass on the rental, was MIA. It was just one issue after another and overall a very bad experience, but again shout out to the staff who were very kind and helpful throughout.
2.0
Poor|Jul 2023
It takes about three hours to pick up the vehicle, and people at pickup location were so rude to customers.
Customer service needs a huge makeover. I didn't end up renting a car because of how rude the woman was. This seems to be a common theme. Very disappointed.
4.0
Mediocre|Aug 2023
Desk person asked if I wanted the Fuel deal to return it empty. I said no, I'll fill it up. She charged me for the fuel deal anyway and I didn't realize it until I turned the car in. Trying to figure out how to get my $66 back that I should not have been charged. Also, the line was 40 minutes long just to get to the counter. The actual car was fine, but the Dollar service is not good.
2.0
Poor|Jan 2023
My flight was delayed, and I arrived at the dollar counter, just after they had closed. There was a lady still behind the counter, who informed me that because I had not arrived within two hours of the predetermined time they had rented my vehicle to someone else. How is this practice even legal being that I had already paid for it? I was forced to take rideshare to my destination and then back again the next day at an expense of more than $120. I am quite sure that I had pre-purchased insurance but dollar could not confirm this so I paid for insurance that I didn’t need , my total charge at the counter was an additional $124.22. The type of vehicle I had requested was not available so I had to settle for what they had. There were four shirts laying on the back seat, so I find it difficult to believe the vehicle had been cleaned , I think that the previous customer had just left it clean. Please let me know how to get a refund.
The rental was very nice and very clean. Pick-up was a little tricky (not knowing the tram ride), but dropping off the rental couldn't have been any easier. I will use Alamo again when visiting Chicago in the future. Thanks...........Joe
My overall experience was very good, however, the pricing for my rental pick up from the airport was ridiculously overpriced! Therefore, I don't think I will choose Enterprise again for those types of trips! Ty
I believe that the car was nearing the end of its rental life, but the service offered, and the employees were fantastic.
6.0
Okay|Aug 2023
Not enough car selection choices. I had done the payment online, bit an additional insurance charge was added to at the last minute.
2.0
Poor|Apr 2023
Poor customer service at this location
2.0
Poor|Mar 2023
I specifically rented a luxury vehicle. When I arrived at the location, they had none available and offered no apology or explanation.
4.0
Mediocre|May 2022
I had to trade my first car for another one because I was getting tickets due to the fact that the license plate had expired a month earlier. Both times the pick-up process took forever. The only place to sit in the dingy office is a ledge along the windows. The staff (only two people) was very nice and helpful but clearly overwhelmed. Even though this office is only four blocks from where I live I'm not sure I want to rent from them again.
We arrived early, so check in was very quick. Easy to pick up the car, easy to return at O’hare. Friendly staff.
6.0
Okay|Sep 2023
The pick-up line was nearly 2 hours long. Counter agent was very friendly, but he could have used help that day. We will not return to Avis unless staffing is addressed
2.0
Poor|Sep 2023
Original reservation was canceled with out notification. Called 4 times the morning of and reservations was trying to charge me double what I was originally quoted after mentioning the lot was empty… never Avis, ever again. lady at the counter, “ I had to fight for this car” -gets in and realizes it’s HEAVILY smoked in…
2.0
Poor|Jul 2023
It was two hrs from the time I stood in line to the time I actually started a vehicle!
10.0
Wonderful|Jul 2023
The staff helping us with pick-up in Chicago at O’Hare was friendly, experienced, and professional. She explained everything thoroughly while making the pick up quick and easy.
10.0
Wonderful|Apr 2023
Drop off someone had to explain process- minimal staff - holiday and like most business just lack of staff. Taken care of and staff was pleasent
Being charged for full tank of gas when we brought tank back full.
4.0
Mediocre|Oct 2022
The price was double what was advertised on Kayak and I used the car for less than a day (over $500 charge). I knew fees could differ but not to this degree
2.0
Poor|Oct 2022
From check in to drop off the experience with Payless rental was horrible! Car was not full of gas all though the paperwork stated it was. Car was dirty (literally trash left in the car), waited in line for pick up for almost 40 minutes…there were only 3 customers in front of us. Had issues with the car immediately as back passenger tire was not keeping air. At drop off they told us there was nothing they could do and that we’d need to call the customer service line. Customer service told us they could not refund our money because we booked through a 3rd party. I would NEVER use this service again or Payless car rental! It was HORRIBLE!
4.0
Mediocre|Aug 2022
The pick up experience at Payless in Chicago was horrible. Our car reservation was for 6am right when they opened because we had had a nightmare travel experience and needed to get home as soon as possible. There was nobody at this time. We waited around for a while as we saw employees arrive for all the other car rental companies. After about 15 minutes and still no one there to help us, I ended up finding a Budget employee that was able to assist as best she good. She reiterated several times throughout the process that Payless does things a little differently than them and she was unfamiliar with their process. Long story short, she ended up miscommunicating something to me (not her fault - she wasn't a Payless employee), leading to an expected nearly $100 charge on my card. The silver lining was that Payless Customer services was very nice after the fact via online inquiry. Quick responses, understanding of my situation, and accommodating to my requests. Although I had a good experience with customer service on the back end, the negative experience I had on the front end is enough to make me not use Payless again in the future.
2.0
Poor|Jan 2022
no one answered the phone at the airport so i cancelled. never again
8.0
Very good|Jan 2022
Car we requested was ready when scheduled.
1 out of 15
Payless Locations in Chicago
Jeep car rental FAQs
Find answers to frequently asked questions about Jeep rentals in Chicago, including policies, rental requirements, and more.
What is the cheapest Jeep to rent in Chicago?
Looking to rent a Jeep in Chicago? The Wrangler Unlimited is an affordable choice, averaging around C$ 57/day.
What rental agencies have a Jeep available to rent in Chicago?
You can find Jeep rentals in Chicago through 2 agencies, including Hertz and Routes Car & Truck Rentals.
What is the most popular Jeep model to rent in Chicago?
The top Jeep model in Chicago is the Wrangler, with an average daily cost of C$ 129. Notably, it's 20% more popular than other Jeep models in Chicago.
How much does a Jeep Wrangler cost to rent in Chicago?
Considering a Wrangler rental in Chicago? On average, it's priced at C$ 129 per day. Our users discovered the best deal at C$ 104 per day.
How much does a Jeep cost to rent for a week in Chicago?
On average, it costs C$ 654 to rent a Jeep in Chicago for 1 week.
Can I rent a Jeep at Chicago Midway Airport?
Yes, there are Jeep rentals available at Chicago Midway Airport if you plan on flying into the city and renting a car for the duration of your stay. Hertz is the most popular rental company offering Jeep rentals at the airport.
Luxury car rentals in Chicago
Find luxury car rental deals in Chicago from well-known providers in the area and save on gas mileage with the options provided below. luxury car rentals in Chicago cost an average of C$ 125 per day. Price data was last updated on 14 May 2026.
Audi A4C$ 95/day
5
2
M
A/C
Audi A5C$ 103/day
5
2
M
A/C
Mercedes-Benz E-ClassC$ 104/day
5
M
A/C
Tips on how to find a Jeep in Chicago
Not sure how to use Cheapflights to find cheap Jeep rentals in Chicago? We’ve got you covered! Just follow the instructions below to find great deals.
Using our search form above, use the drop-down menu to select either “Same drop-off” or “Different drop-off” location for your Jeep rental in Chicago. Then select your, or your driver’s, age.
Next, search for and select your rental location if you don’t automatically see your intended location pre-filled in the form. If you selected “Different drop-off” you will also want to select your destination. Don’t worry, you can change all of this later if you need to!
Then click the calendar icon and choose the dates you wish to have your rental car, and give us a timeframe of when you can expect to pick it up and drop it off.
Finally, hit that search button and we’ll do the rest by providing you with great deals on Jeep rentals in Chicago for your trip.
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