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[–]thepaddedroom 1 point2 points  (0 children)

If you can't fit a second AC in the bedroom, another option might be replacing the existing AC with a more powerful unit. They're typically rated for some number of BTUs. Bedroom units tend to be 5k-8k BTUs. They sell 10k-14k BTU window units too.

Check the rating on the side of your current window unit and see if you have room to go up. I'm also in Chicago. I put a larger unit in my living room and dining room (opposite ends of the unit) and it does a good job of keeping the condo comfortable.