For any serious runner, looking through training plans inevitably leads to the discovery that they all want you to do hill repeats. Hal Higdon (basically the godfather of running in Chicago), recommends that hills be a quarter-mile or longer. If you have never been to Chicago, allow me to clue you in - the city is flat. The largest and longest "hills" we have are the on and off ramps for the expressways. Finding long stretches of elevation are difficult, and I cannot think of any that are a full quarter-mile long. However, here are a couple of spots that I have found that make for at least a somewhat noticeable incline.

• Lincoln Park, just north of North Pond, near the entrance to the Diversey Yacht Club. It is long enough to at least make you feel it, though it is not very steep. There are lots of trees around, so it is nice and shaded during hot days.
• Cricket Hill, between Lake Shore Drive and Montrose Beach. This staple of the Montrose Beach area has a gentle incline for the first half, and then a steep incline for the last half, rising about 45 feet from the base. The north west side of the hill is currently under construction while the city puts in a new turf field and an 8-lane running track. This is going to get a lot of runner attention once it is finished.
• Solder Field South Lot, south of Burnham Harbor and Solder field, accessible via the Lakefront Trail, this sledding hill is a short but steep incline. I would estimate that it is about 200 meters from bottom to top, and probably a 30 foot rise. Nothing spectacular, but we take what we can get.
• Horner Park, bounded by Montrose, Irving Park, California, and the river. The incline is not very steep, and I would be surprised if the hill crested at more than 15 feet. However, it is about the longest stretch of incline you will find in a city park.
• Humboldt Park, next to Little Cubs Field - more of a grassy knoll than a hill, at least it is something. Also, there are lots of paths all around Humboldt Park, making for a nice run. While there, check out the gorgeous field house.
• Parking garages - these are spread throughout the city, with lots of them being downtown or at movie theaters. I have used the one at the Regal City North a couple of times. It is not as fulfilling as running on the grass hills, but I find the concrete and cars are still better than trying to run on a treadmill.
• Treadmills - the ugliest of the suggestions, but sometimes it is the only way. Set the thing to the steepest it will go, and start out slow.

If I find any others, I will update the list. My runs are almost exclusively on the Lakefront Path and on the north side of the city, but if I hear of anything elsewhere in the city, I will gladly share it.