Weird Winds

FlyChicaga

Vintage Restoration
So get this. We pull up ATIS at MDW, winds are reported around 190 at 18 G 22. While taxiing out, we notice the windsock is showing something much different. So we ask current winds, and tower says "280 at 10." When cleared for takeoff, the winds were reported 310 at 10, with a shear of 20 knots reported on runway 31C.

Well we get to Milwaukee, about 20 minutes flying time away, and the winds are 190 at 12. So... winds in Chicago are northwesterly, but in Milwaukee are southerly?

We kept thinking of why that was the case, wondering what you all think. (Rain showers were in the area, a line of storms/rain stretching the length of Wisconsin moving east between Chicago and Milwaukee.)

When returning to MDW after our MKE flight, winds were 230 at 10.
 
We thought it might be a front, but the winds shifted back. We think it was some kind of wind burst caused by the rain showers that moved through. Somewhat like a microburst, but not as noticable. I looked at our weather computer later, and it didn't appear that a front was nearby.
 
Anything is possible hehe. I still think maybe one (small/weak?) front pulled through, causing a veer in the wind, then there was another one (the warm front a ways away) which was now taking affect with it's winds causing them to back again?
 
KMDW 241753Z 23007KT 10SM FEW020 BKN032 OVC150 09/06 A3003 RMK AO2 RAE00 SLP171 P0000 60026 T00940061 10094 20072 58009
KMDW 241735Z 23006KT 10SM SCT018 OVC030 09/06 A3005 RMK AO2 RAE00 P0000
KMDW 241653Z 23009KT 10SM -RA OVC024 09/06 A3005 RMK AO2 RAE1559B36 SLP179 P0000 T00890056
KMDW 241612Z 28004KT 10SM BKN020 OVC150 08/05 A3005 RMK AO2 RAE1559 P0000
KMDW 241553Z 31010KT 9SM -RA FEW020 SCT027 OVC150 08/05 A3005 RMK AO2 PK WND 18026/1540 WSHFT 1538 PRESRR SLP178 P0019 T00780050
KMDW 241519Z 19018G22KT 3SM RA BR OVC029 07/05 A3003 RMK AO2 P0010
KMDW 241453Z 17014KT 5SM -RA BKN033 BKN060 OVC080 07/04 A3005 RMK AO2 PRESFR SLP180 P0004 60007 T00720044 58013

The METARs from the time I'm talking about...
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PRESRR, so it rose, wind shifted due to frontal (or disturbance passage, maybe upper front?) then it started falling slowly, probably since there was another system coming in. Just my 2 cents of course.

Probably cold then warm front, since cloud bases rose and temp increased.
 
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