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I had always envisioned myself as a fall bride, but once we actually got engaged (December 2010) and did the math on how much our wedding would cost, we ended up going with May 2012. Plus, I found that when I was calling venues in January 2011 for availability in October and November 2011, that everywhere was already booked up! :) I am a big fan on May brides now, as I will be one!! 
Seeing as your friend is getting married in Oct and share same group of friends, I would go with May.
I am biased to fal because I am actually a fall bride....and Im from Illinois too! Well with the season being pushed back and all wacky we still decided on an october wedding. I know my good friend got married last year on sept 18th and she had a beautiful day to get married on. No rain and No cold weather! My FSIL got married last year on Nov. 7th and she had warm weather too! Its just one of those chances you are gonna have to take.
I dont know which area in Illinois you are from but it always rain the last two weeks of May in my area! Check the farmers almanac for both of those dates....every library should have the 2012 version now!
Good luck and keep us posted on which date you choose!
I think May can still potentially be cold in Illinois. I remember this year that I complained a lot because it took so long to get warm! It sounds like you're planning an outdoor wedding. I think in either May or September would be fine, but remember to plan B! Plus, they say rain on your wedding day is good luck!
Well, I'm partial to the end of May :)
It was 104 today here so weather this year can never really be a certain predictor of weather next year.
If the flowers and the feel of spring is more you, then go with that.
I went through your exact dilemma. I went back and forth between May and September as well and live in WI. I have always loved spring, the fresh air smells so dang good after a cold winter! Yet, I also love fall.
My big factor was like you, the weather. I wanted it to be nice, not cold and less chance of rain. I wanted September thinking less chance of rain but then someone pointed out that labor day can be pretty cold and I was looking at Sept 15, 2012 so figured I was taking a chance. Sure it can be cold (and rainy) in May but my thought was you're coming out of colder months so even if it's not THAT warm in May, it will still feel nice. It's not like going from 90 degrees to 60 which can certainly be the case in September.
I did a FB poll and asked friends for their opinions and the majority picked September, they had great envisions of a fall wedding. My problem is to me, September in the midwest doesn't really seem like fall, it's more like the ending of summer. October is fall when the leaves are turning, etc.. I ended up chosing May and even after having an unusually cold and rainy May this year, I'm glad I did. I'm going with a rustic elegant wedding with touches of birds, etc.. If I had done September it would've been harder to have somewhat of a theme (for me anyway)
Good luck in your decision and remember that no matter what month you pick, there is always a chance of bad weather. If there were a guarantee, this would all be too easy :)
I live in NC and it's unbearably hot and humid here in the summer and I NEVER envisioned myself being a winter bride...hence Fall it is!
...however having lived in Milwaukee briefly and knowing how finicky the weather there can be, i think you're safest bet is a fall wedding!
*not sure why my prior post uploaded before i finished typing! :) *
Thank you everyone for your responses!
@vicozzie: Your wedding sounds gorgeous! I do agree, September definitely seems like more of the "end of summer". Which is ok with me.. I wasn't crazy on having a "fall themed" wedding, I just want it laid back but classy. :) I'm thinking creams with a mixture of other lighter greens, browns, taupes, lavender... I don't think I want to stick to strict colors, it seems to make everything tougher!
@d_mari3: Good idea to check the Farmer's Almanac.. it can't hurt!
SO and I were just talking.. he doesn't care at all either way... so ... up to me I guess! lol.
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So it's raining. And extremely unseasonally cold for here... But, yes.. I am (was?) hoping Saturday September 8th, 2012 might be our wedding date.
But then I got to thinking, although fall has always been my favorite.. I love peonies, and my SO and I garden, so spring is like a renewal, being able to plant again. I love that everything's green and pretty... But..we also love apple cider and football and bonfires ;)
But the fact that it's randomly raining and way colder than I like for the beginning of September.. It makes me wonder.. My whole dang life my mom's always told me to never plan outdoor events/parties because it rains... and she's right, it usually does! We can't do late September because some very good friends of ours are tying the knot on Oct 13th. I don't want it to be too close, it'll be the same big group of friends going to each one.
It's a tough choice.. end of May or beginning of September?
What would the bees pick??