My roommate and I recently celebrated a landmark occasion for two young people living in Chicago: We resigned our lease. Lucy and I have lived together since February 2009. In those 18 months we have shared three addresses, including a nearly year-long stint at our current apartment. Renting in Chicago is an uphill battle, and one I wish I was better prepared for the first (or second, or third) time around.

My first apartment was, well, a first apartment. Tiny, dusty and poorly insulated, it seemed it would work just fine for two busy students. Lucy moved in after my original roommate decided to extend a semester abroad, and together we suffered through blown-in windows, a series of preposterous $400 electric bills and an alarming number of house centipedes. Our faceless landlord deferred all calls to her handyman, whose duct tape fixes were no match for a 60-year-old building.

Lessons learned: Meet the landlord, look at the space two separate times, check the windows carefully and ask for a copy of each season’s utility bills before signing the lease.

Desperately wanting to get out of our dusty, sunless, second-floor cave, we started our apartment search early, knowing that May and June are competitive rental months. We found what seemed to be the perfect place quickly, and took it as a sign that our luck was changing. It was sunny, inexpensive and humongous. We were able to leave our old lease early and moved in with fervor. We painted, decorated and rearranged until we had an apartment we loved.

Alas, three months into bliss, we found a loaf of bread dragged into the living room from the pantry. We had rats. After a few weeks of back-and-forth spats with a landlord who was convinced it was mice, a visit from an exterminator confirmed otherwise, and the bread bandit was quickly caught. Unfortunately, the entry point the exterminator identified was not the only one, and we had visitors again on a rainy October evening. Lucy and I each packed a bag and stayed with friends until the legalities of breaking our lease were sorted out.

Lessons learned: Don’t take anything as a “sign,” don’t think about painting for at least six months and ask the previous tenants why they are moving out. Put code violations in writing immediately, take pictures and notes of everything in question and save receipts if you are forced to spend any money related to apartment maintenance. Be familiar with the Chicago Residential Landlord-Tenant Ordinance; it is important to understand your rights, your landlord’s responsibilities and what conditions are considered code violations.

Already feeling defeated, we only had two weeks to find an apartment in late October. We desperately wanted to find a place we knew would stick, but didn’t have much confidence there would be one open in our price range. Having practically memorized the codes in the Chicago RLTO by now, we scrutinized every place we looked at. We opened and closed windows, turned on faucets, checked outlets and had someone walk upstairs so we could listen

for squeaky footsteps.

After seeing 10 places in two days, we found an apartment still being rehabbed that fit our checklist. For the price, we worried it was too good to be true. But 10 months later, we’re still there, which is more than we can say for the last two apartments. When water came streaming into a bedroom in the middle of the night, we had workers at the door at 8 a.m. When the heating bills were outrageous, the landlord had someone take a look at the duct work.

In Chicago, finding the winning combination of perfect apartment, perfect price and perfect landlord is practically unheard of. Even more impossible is finding it the first time around.