Without knowing the specific parcel you refer to, it is difficult to offer anything more than a cursory overview - so here goes.
Construction within the past five or so years have integrated specifications that call for porous drain tiles on the interior of the lower level (below the floor) and exterior to the building's footing. This is placed in a gravel mass to enable soak through and run off. To further facilitate appropriate handling of too much water newer buildings will have ejectors and sump pumps. So long as these items are present, you should be good to go with relatively little to worry about as it regards flooding.
As with any real estate purchase, you will be well-served by having in your corner the best possible advocates that include a well-informed real estate professional, a professional and experienced home inspector, a good attorney and a credible and intelligent lender.
There's a ton of inventory in Wicker Park, having a good realtor on your side will enable you to gain much needed insights to make the best possible decision.
Feel free to reach out to me if you would like assistance - 773.848.9241.
The Real Estate Lounge Chicago with @properties