If you’re planning a trip to Chicago, one of your biggest transportation questions may be whether or not you rent a car. In such an accessible city, you have the option of just using public transportation or having the freedom that a rental car gives you. In this post I share all the information you need before renting a car in Chicago, Illinois. Use this as a resource while planning your upcoming trip to Chicago so that you can manage navigating around the city. Here are my best tips for renting a car in Chicago, Illinois:

Best Tips When Getting a Rental Car in Chicago

1. Plan whether you need a car for your Chicago trip.

You do not need to rent a car in order to experience Chicago, Illinois. With Chicago’s public transportation system, getting around the city is a possibility whether or not you’ve decided to rent a vehicle. In some cases taking public transportation is cheaper than paying for parking so it’s up to you to decide whether or not the experience of renting a car in Chicago was worth it for your time here. There’s also the possibility of reserving a taxi in Chicago; we could be more information on all the way to get around Chicago here.

2. Consider how tight parking can be in some places around Chicago.

Not all streets are created equally; some are filled with potholes and others can barely fit two cars actively trying to pass each other. Before you go renting the biggest truck you can find, I recommend considering something more moderately sized so you know you’ll have access to the most parking. If you are perfectly comfortable paying to reserve spot 100% of the time then size doesn’t matter, but if you’re trying to find parking around Chicago then a smaller vehicle is more likely to find a spot.

3. Plan for how crowded Chicago can be for an unfamiliar driver.

Along with how tight parking can be, some areas of the city require a little bit more patience and attention in order to get through. You can find that both pedestrians and drivers always have somewhere to go so they try to squeeze by even if it isn’t there a lot of time. You should be extra watchful especially if you aren’t used to driving through areas like that.

4. Always have the insurance option when renting in Chicago.

No matter how safe and experienced of the driver you are, I always recommend the insurance option. There’s nothing worse than doing everything you’re supposed to and somehow your car gets gets more action then you planned.

5. Create digital backups of paperwork & a video of the car for safe keeping.

I’m a huge advocate for creating digital back ups of everything! I recommend taking pictures of all car rental documents you receive through the entirety of the trip and even going further and recording a video of the car as insurance .These digital back ups will allow you to have proof of documentation as well as a quick way to navigate through all the paperwork without losing anything. I explain how I create digital backups while traveling in a car rental here.

6. Budget how much parking in Chicago can be.

Some residential areas in Chicago have free parking, but if you’re staying near the loop you may find that your parking comes at a cost. Budgeting how much parking may be in the area you’re staying in can make a huge difference on whether or not you want a rental car in Chicago. Additionally if you’re staying in a hotel the office parking, I recommend you double checking how much your daily parking fee will be so that you can budget appropriately.

7. Think about rental car pickup and drop off locations compared to where the airport is.

Chicago has two international airports, if you’re planning on renting a car near the airport, you need to clarify which one you will be closest to. I created a full guide that shares which airlines fly into O’Hare airport in which airlines fly into Midway airport here.

How to Find Cheaper Car Rental Options in Chicago, Illinois

Look at car rental rates further away from the airport.

It isn’t just the sandwiches that are expensive at the airport, it’s everything. Somewhere between merchants having additional fees in airport areas and the accessibility of having a car rental when you land you can expect that the price is a little bit steeper.

Reserve your rental as soon as possible.

At this point in time it seems like the cheapest rental car is the one that you can actually get your hands on. I always recommend booking your things as early as possible so that you can have a handle on the price and I share that opinion with renting a car. It seems like a lot of places dip in stock and you don’t want your poorly time reservation to happen at one of those dips.

Fill up the gas tank before returning.

You should always fill up your gas tank before returning a rental car because somehow they find the most expensive gas in the area. You don’t want a surprise bill in the end because they had to fill up your tank and it’s something you didn’t budget initially.

Renting a Car Near Chicago’s O’Hare International Airport (ORD)

Ranked as the fourth busiest airport in the world and located on the north side of Chicago is O’Hare international Airport. With over 30 airlines that service ORD, you’re more than likely to fly into this airport as you visit Chicago. If you’re flying into O’Hare airport make sure that it is O’Hare airport that your car rental is at. If you’re looking more information on flying into Chicago, Illinois you can refer to my Chicago Travel Guide that shares which airlines fly into O’Hare and Midway Airport.

Renting a Car Near Chicago’s Midway International Airport (MDW)

Located on Chicago’s Southwest side is Midway International Airport. Compared to O’Hare, only a handful of airlines service Midway like Allegiant Air, Frontier Airlines and Southwest Airlines. If you’re flying into Midway airport, double check that your car rental is near Midway airport. You can find all the airlines that fly to Midway here.

Best Apps for Driving Near Chicago, Illinois

Best App for Renting a Car Hourly in Chicago

If you’re interested in renting a car but only for a short amount of time I recommend that you check out Zipcar. If renting a car in Chicago is out of your budget, you may have better luck renting a car hourly for a more reasonable price with Zipcar. I find that Zipcar is really flexible and it allows you to rent a car to get some things done and return it before the day is over. If you find that your schedule is a bit more flexible, I recommend giving this a shot.

Download Zipcar app from the App Store here. | Download Zipcar app from the Play Store here.

Best App for Finding a Car Rental in Chicago

If you’re interested in finding a car rental closer to the city, I recommend checking out the Turo app. Turo is a peer to peer car sharing network that allows you to rent a car from another Chicago local. They do have some eligibility requirements like being 25 years old or older, make sure you refer to their eligibility page so that you can make sure that you’re able to rent a car from Turo before you show up.

Download Turo app from the App Store here. | Download Turo app from the Play Store here.

Best Apps for Finding Parking Spots Around Chicago

For finding parking around Chicago I usually refer to two apps: Spot Angels and Spot Hero. If you check out their map feature you may find that one of them has a closer parking lot to the location you’re intending on going to than the other; using them both makes me feel like I have the most coverage.

Download SpotAngels app from the App Store here. | Download SpotAngels app from the Play Store here.

Download Spot Hero app from the App Store here. | Download Spot Hero app from the Play Store here.

Best Apps for Planning Transportation Around Chicago

If you’re planning to sprinkle in some trips on Chicago’s public transportation, I recommend that there’s a few apps you download. I’ve written a post all about planning transportation around Chicago, Illinois which includes information on public transportation as well as navigating the city via taxi and on foot. You can plan your transportation around Chicago with this blog post here.