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You can cut the brown off, but it will only continue down the leaf killing the whole leaf. These will not grow back. They will, however, grow more from the top of the plant. It would be best to find out the cause of the problem. If this is in container, then it would likely be due to over- feeding, over-watering, or compacted soil.

This collection of articles will give you information on the care of these plants: https://www.gardeningknowhow.com/edible/fruits/pineapples/

These type pineapples will never get as big as one you would see from the store. To do so would require that you live in the proper area, OR that you can provide its natural conditions in a larger pot of at least 5 gallons. More is much better though.

This article will help: https://www.gardeningknowhow.com/edible/fruits/pineapples/care-of-pineapple-plants.htm

Depending on the cultivar, pineapple plant takes 2-3 years after root formation to fruit. That it does poorly in winter indicates you need to change your care. Only a very healthy plant has the energy to produce fruit. Pineapple is a tropical plant and needs to have moist, yet fast-draining soil. Do not let it dry out and do not let it sit in water. To ensure good drainage, add some sand, perlite or cactus mix to regular potting mix. It requires supplemental light in Chicago winters. This article gives a tip to trick the plant into fruiting. I hope it works for you. https://www.gardeningknowhow.com/special/children/planting-pineapple-tops.htm

Getting these to fruit indoors is a bit of a task. I'm afraid you may be looking at another two years once you correct some of the environmental factors. You may even have multiple plants before then!

Pineapples need an incredible amount of light. The equivalence of the sun. This means that you will need about 200 watts of light per plant. Metal Halide and High Pressure Sodium ballasted systems are still the standard, however, if you are willing to spend the money, then you can invest in a High End LED panel.

The cheap panels will not suffice here, since they need more of a spectrum than cheap panels provide. All high end panels are at least 9 band, and better is 12 band light spectrum. If you decide to go with an LED, make sure you use the actual watt draw as a reference and not equivalence, since pineapples will be picky about this.

If none of these are feasible, then it will need to be out in the sun for well over 8 hours per day all year.

Otherwise, if you can't provide adequate light to the plant, it should be expected to only produce foliage, and have a similar care to Bromeliads.

Usually, overwatering. This leads to infection. These articles will help: https://www.gardeningknowhow.com/edible/fruits/pineapples/dealing-with-pineapple-problems.htm

https://www.gardeningknowhow.com/edible/fruits/pineapples/care-of-pineapple-plants.htm

You can find a place to set it where the ants/critters won't get it. If you set it in a cupboard will the ants find it? You can also try setting a dish inside another to make a moat (to disourage ants) but that might increase the humidity around your top and cause it to rot.

https://www.gardeningknowhow.com/special/children/planting-pineapple-tops.htm