Finding where to park in Chicago is hard to do if you don't know where to look. I've done the whole circling and circling blocks and neighborhoods to find parking near my event and not finding any, and then end up parking so far away the event is almost finished by the time I arrive. (Or I decide not to go because of the parking issue!)
Of course, parking anywhere outside of the major commercial centers of Chicago is going to be easier by far. This is also not intended to be a complete, authoritative, or fool-proof guide (especially when other Chicagoans catch on to these little tips). However, after learning these little tips, I haven't paid for parking since!
How to find where to park in Chicago:
1. Don't be afraid to walk. Some people's hang-up is that no matter how early to an event they arrive, there is still no parking right in front of the venue or building. Unfortunately- this is how it goes. Learn how to walk- because I guarantee that just a couple blocks away (and in perfect walking-distance) you can find a parking spot. Unless you are vying for a spot in the MIDDLE of downtown (which is going to be impossible during most hours of a weekday), a free parking spot in the area that is close enough to walk can be found almost every single time.
2. Read the signs. Just because there's a "NO PARKING" sign next to the empty street doesn't necessarily mean NO PARKING ANYTIME.
The sign below says NO PARKING 3am-7am, December 1- April 1 or when snow is over 2 inches. SO when its 7:15 on April 2nd, and sunny and beautiful outside- you can park there!
The sign below says NO STOPPING, NO STANDING 6am-6pm Monday - Friday. SO on Saturday and Sunday you can park there anytime, and after 6pm Monday through Friday you can park there as well.
The sign below says 15 minute standing zone (use flashing lights) between 7am-6pm Monday through Friday, 4pm-6pm Saturday, and 8am-1pm Sunday. SO you can park there any other time for more than 15 minutes and be fine, unless it will impose on the times that are listed on the sign.
Understanding what is actually written on the sign will help you find where to park in Chicago a lot quicker. These are just a few of many examples!
3. Check the residentials. If there are any residential areas in the neighborhood, there is likely going to be free parking there. Check and make sure its not a permit-required street, because some areas require permits only between certain times. Neighborhoods like Lakeview, Lincoln Park, Wicker Park and Lincoln Square are all full of shopping, bars, music venues and clubs, and also are surrounded by residential areas. Park nearby and walk to your event!
4. Love the CTA. If you are coming in from out-of-town and you've come in to visit the city for a day, lose the car and take the CTA! You are going to find more and better parking the further away from downtown you go. Taking the CTA as you sightsee instead of traveling in a car will give you the opportunity to enjoy the city more thoroughly. It will end up being cheaper, because a day-pass for the CTA is only $5.74. (Right now that's equivalent to almost a gallon and a half to two gallons of gas, and that's not much at all.) If you take the CTA more than just a round-trip (which is $4.50), your pass will have paid for itself.
If you love the CTA and just don't know what to do on it, don't worry! I've got a guide for that too in my Stop-by-Stop, Line-by-Line preview of the 'L'! Everything you need to know about every stop on the CTA!
5. If all else fails, check this map out: http://en.parkopedia.com/parking/chicago/
Parkopedia is a website that calculates the price of parking in the exact location you are trying to find parking. Just put the address in the search bar and the times you are trying to find parking. The nearby parking garages, parking meters and how much they charge per hour, and free street parking will all come up according to the area you are trying to park in.
Happy Parking! If you have any more tips or advice, let me know below!