My -800/MDW experience:

It was a challenge.

Normally, always a Flaps 40/Brakes 3 landing. (SOP with <7000') With very light weights, Brakes 2 will work. Gusty winds = Flaps 30 was acceptable if 40 would result in Flap Load Relief issues. Landing distance not a problem here. BA reports must have been "Fair" or better. We used WSR performance calculations. Pay attention to that tailwind component! If you know MDW, you know they don't like using 13.

Warm weather takeoffs, greater than 85ºF or so, = 27K, Flaps 25, Alternate bleed, with winds and altimeter corrections to get off and to the west coast. Generally started bumping pax starting around 88º, depending on winds. OGG and LIH T/O performance was even more limited.

It was fun.