Car rental in Chicago
Downtown Chicago is well served by the L and by walking. The car earns its keep on the drives out — along the lake, into Wisconsin, and across to Michigan.
Tolls on the way out
The Illinois tollway network surrounds the city and is largely cashless. Rental cars are enrolled in a toll programme, and as elsewhere the rental company adds a service charge on the days tolls are incurred. If you are heading to O'Hare, north to Wisconsin or west on I-88, you will use them.
Winter is a real consideration
Snow and lake-effect conditions run from late November into March. Rental fleets here are equipped for it, but all-season tyres are not snow tyres — leave more braking distance than feels necessary. During declared snow events the city enforces winter overnight parking bans on designated arterial streets and tows aggressively.
Parking downtown
Loop and River North garages are expensive, and street metering runs long hours. If you are staying downtown and only driving on one or two days, collecting the car on the day you need it is materially cheaper than paying for overnight garage storage across the whole trip.
Drives worth taking
- Lake Shore Drive— short, and the best introduction to the city's geography.
- Indiana Dunes— about an hour southeast along the lake.
- Milwaukee— 90 minutes north on I-94.
- Saugatuck and the Michigan shore— around two and a half hours around the lake.
| Best class | Compact in summer; SUV with AWD in winter |
|---|---|
| Tolls | Illinois tollway, cashless; service charge applied by the rental company |
| Airports | O'Hare (ORD) and Midway (MDW) |
| Watch for | Winter overnight parking bans on designated streets during snow events |
Questions
Renting a car in Chicago
The things worth knowing before you book, including who you are booking with and what leaves your account today.
In Chicago
How do Illinois tolls work now that cash has gone?
Entirely electronically — Illinois removed cash from its tollways in 2020 and there are no booths left. Either take the rental toll programme, or pay online within the stated window, or expect violation notices with fees added.
Is winter driving in Chicago a problem?
It can be, between December and March. Ask the counter what the vehicle is equipped with, allow far more time than the map suggests, and remember lake-effect snow arrives faster than forecasts imply.
Booking with RentalForCar
Who am I actually booking with?
RentalForCar is an independent car rental reservation service operated by Affluence Hospitality LLC. We are not a rental company and we do not own vehicles. Your car is supplied and operated by a licensed third-party rental company, and the rental agreement you sign at the counter is with them.
What exactly is charged today, and what at the counter?
Today: a deposit against the rental plus our service fee, both itemised before you pay. At the counter: the remaining rental balance, local taxes and airport fees, and any extras you add on arrival. Nothing is added after you book that was not shown to you.
Can I cancel, and what does it cost?
Free within 24 hours of booking. After that a flat $50 fee applies and the rest of your deposit is refunded to the original payment method. No cancellation window is hidden in the small print.
Will I get the exact model in the photograph?
You are guaranteed a vehicle in the class you booked. It may be that model or a comparable alternative, which is why every listing says "or similar". If you need a specific model for a specific reason, call and we will tell you honestly whether it can be confirmed.
Do you take card details on the site?
No. Card details are entered on a secure payment page, not in our forms, and we never handle or store card numbers ourselves. We will never ask for a full card number by email, chat or text.
What happens if something goes wrong at the counter?
Call us on the number at the top of the page with your booking reference. We deal with the rental company on your behalf — a vehicle class that is unavailable, a charge you did not agree to, or a booking they cannot find.