1. Seeing the last open spot on the street covered in an army of lawn furniture.

2. Or realizing that there is at least one other driver who values saving a parking space over the safety of their passenger child.

Flickr: 58412763@N00
This is some straight up Florida shit.
3. When you get a ticket for not having a city sticker if you don't actually live in the Chicago city limits.

Via Twitter: @jasonloper
Because GOOOOOD LUCK fighting that ticket, son.
4. When you have no choice but to brave the Kennedy.

Via Twitter: @search
Good luck, brave soldier.
5. Driving when it's snowing, and seeing all the lane lines get thrown out the window.
6. When some idiot traffic reporter refers to all the expressways by their numbers and not their names.

Via gapersblock.com
Look, I just want to know what is happening with the Ike. I don't give a shit about whatever the hell "the 290" is.
7. When there is a pothole the size of the sun in front of your house.

8. When the pothole in front of your house finally gets "dealt with."

Flickr: 28222353@N00
This is not a fix, this is a trap that you might set for the Roadrunner.
9. Missing your freaking exit and having to go through the I-Pass booth AGAIN.

10. When your local alderman pisses somebody off, and your street doesn't get plowed.

11. Leaving your car somewhere overnight, and coming back to find it covered in parking tickets.

Flickr: 15865493@N00
Chicago Parking Enforcement: The only people on earth who can convict someone for the exact same crime 6 times.
12. When it's snowing, and a stop sign is more like a suggestion.

13. When a sink hole opens up on your street because of a busted water main.
Via imgur.com
Thanks, Rahm.
14. Running into the post office for ten seconds, and when you come back, it's booted.

This won't cost $1000 or anything.
15. Being late for work while parked on a street that hasn't been plowed.
16. Construction on Lower Wacker Dr. and your GPS doesn't know any other way to get to where you need to be.

17. Realizing that all the salt they pour on the streets to keep them from freezing is slowly rotting away your car.

18. Being pretty sure you're on time for work... until you hit the Hillside Strangler.

Via en.wikipedia.org
19. When the parking meter is jammed, and you can't remember whether it's legal or not to park there.

20. Realizing that the street you need to get down is closed for street festival reasons.

21. Really needing to park on the street, and only seeing spots that need to be dug out, first.
22. Seeing how atrociously other drivers treat cyclists.

23. When you're in gridlocked traffic in a blizzard, and you realize that this is actually a dangerous situation.

Via Twitter: @search
24. Seeing big rigs speeding next to your car.

Via Twitter: @search
25. Agonizing over whether or not your car is up for forging through a flood...

Flickr: 62614925@N00
Oh, look, it's a new ocean. In the street.
26. Aaaaaaand realizing way too late that you've seriously underestimated the flood waters.

Via Twitter: @search
27. When you take Lake Shore Drive and end up having an atrocious trip.

Via Twitter: @search
28. Knowing that your car could be towed at any second, for any reason, to any corner of the city.

Flickr: 55098830@N04
THAT'S JANUARY. THAT'S JUST ALL OF JANUARY.