Free Parking In Chicago And Everywhere Else

free parking monopolyI won’t think twice about spending thousands of dollars to travel across the globe, but ask me to pay $20 to park my car and I’ll reach for a barf bag. It’s one thing to splash out on a nice hotel room, a fancy rental car, meal or a nice souvenir, but quite another to fork over a bunch of my money just to park your car. Even the best parking spot doesn’t taste good, look nice in your house or give you a sound night’s sleep.

But I’ve found that if you’re willing to walk a bit, sometimes quite a bit, you can get a free parking space almost anywhere. Take Chicago, for example. In August, while in the process of relocating back to the Second City, we scored a room at the Hyatt Regency Chicago, just off of Michigan Avenue on East Wacker Drive for just $55 per night on Priceline.

I knew the parking would be expensive and was pretty sure I wasn’t going to pay for it, but I almost burst out laughing when the valet told me their policy: $52 a night, valet only. No chance was I going to going to pay something very close to my room rate just to park our car, so I dropped my family and baggage off and drove due west for a mile across the Chicago River. In River West, a neighborhood filled with condos, I found a free, yes free, parking spot on Fulton St., between Union and Des Plaines.

It was a very pleasant 15-minute walk along the river back to the hotel and I safely left the car there for 2.5 days, saving over $100. I’m not going to pretend that it’s easy to score free parking in Chicago – depending on the day and time you’re looking, it can be quite difficult or relatively easy. And sometimes you feel like you need to consult a lawyer just to interpret all the signs. But the point is that if you aren’t hostage to the extortionate rates that hotels in big cities charge.

Now there are all kinds of apps out there to help you find parking, but I’m old school. I like to just look around. And I don’t just boycott paid parking lots in hotels, either. If I’m going on an extended trip, I look for hotels near the airport that offer shuttles plus free parking, which can save you a bundle. For example, before a three-month trip to Europe this summer departing from Dulles, I found a hotel in Herndon that would let us park there for free for the duration of our trip. Sometimes the cost of the room is cheaper than what you’d pay to park.

And over the last 15 years, I’ve attended dozens of sporting events and concerts at major stadiums and arenas across the country and I almost never pay to park in the designated lots. Some venues are harder than others, but I have never paid to park at the United Center in Chicago, for example. I always park in the residential area only a few minutes from the arena and not only is it free, it’s also easier to exit after the event is over. Most people just follow the flow of traffic right into the paid parking lots but don’t follow the crowd. Go your own way and park for free.

[Photo by Alan Cleaver on Flickr]