Flying into Chicago Midway (MDW) and planning to drive? Here’s how to pick the right car, use transit when it’s faster, and navigate tollways and neighborhood parking like a local.
Pick‑ups, returns & the Orange Line
Compare Chicago car rental and choose off‑peak pick‑ups to speed through counters. If you’re staying in the Loop, the CTA Orange Line often beats rush‑hour traffic—park once and ride the train when it makes sense. On return, photograph the fuel gauge and exterior as you hand over keys.
City vs. airport: which is faster?
For neighborhood stays, car rental options can reduce shuttle time. Flying out of ORD? Check car rental options and plan a simple one‑way return to match your flight.
Tollways, I‑Pass & parking rules
Chicago’s expressways are cashless; learn the basics and avoid surprise bills with car rental options. For parking, watch street‑sweeping dates, follow permit signs on residential blocks, and use apps to reserve a garage near your hotel.
Car class, winter prep & garage clearances
Compact sedans fit tight street parking; midsize SUVs add confidence in winter and make stroller loading easier. Confirm garage clearance for tall vehicles (many downtown garages post limits around 6’6”). Pack an ice scraper and gloves from October to April.
What to bring & what’s included
First‑time renter in the U.S.? Review car rental options so you arrive with the right ID, card, and driver list. Hola Car Rentals bundles insurance options so you know your max out‑of‑pocket and can choose value or maximum protection in minutes.
- Free Cancellation up to 48 hours before pick‑up.
- Cashback on tolls when tollways are unavoidable.
- No additional fees and clear fuel policies.
Lock your dates and pick the class that fits your neighborhood parking reality—then enjoy the Windy City on your own schedule.
