ChicagHos

SarahBethBR

We are planning on a trip up there sometime next year, but were tentatively thinking of Spring or Fall.  But now we're tempted to take advantage of the Southwest sale and go in January or February.Am I crazy for considering a vacation to Chicago in the winter?  I've been to Chicago once, when I was 14.  It was late November and it snowed, and I thought I was going to die of shock.  We weren't outside a ton but when we were, I remember how insanely cold it was.The price difference in the flights is about $200.  I haven't checked hotel prices so I don't know if tey're any cheaper in the winter.  I think it is important to note that neither of us has a real coat or any winter gear, so we may have to invest more than $200 in order to not die of hypothermia.

lindsayll

Pay a little more and go in the spring.

FallinAgain

I like winter.  Snow is pretty. Sweaters are soft. But, man, Chicago is bleak in January and February.  It's cold and gloomy.  The pretty Christmas decoratons are gone and the city is just pretty much hanging in there waiting for spring. As far as costs, I think you are right that the winter gear you'd need will cost more than the ticket difference.

SarahBethBR

I like winter. Snow is pretty. Sweaters are soft.This is really the only thing that's making us even consider it.  We've never really experienced winter and we'd like to.  But I think I'd rather experience winter from a log cabin with a hot tub with lots of warm stuff around me.  And maybe the option to ski or play in clean snow.  I'm worried that a Chicago winter will just scare us and make us miserable. :/I think we'll just wait. Thanks for the advice.

FallinAgain

Yeah, I think for a good winter experience, you want country not city winter.  Concrete is just cold and gray.

lindsayll

Yep, I loved December, hated January and February.  I feel the same way about NY.  Even though people complain that Chicago is the worst place for winter, it's not that much worse than NY.Chicago in the spring is really pretty.  I love how the parks come alive and all the pretty flowers planted along Michigan Ave.  (assuming the city still has some money left in the coffers to do it)

MamaKin

i wouldn't do it, only because there's so much outside-time on a chi-town trip.  you're always walking somewhere, even if it's to get to the bus/train/cab.  especially if you aren't used to cold, you'll probably be sorry.  i'd wait until the spring... you just don't know how beautiful chicago is until you're there on a 72-and-sunny day and can walk(/shop!) for miles and miles and not even think about it.  totally worth spending a little more, imo.   

heatherkj

We just went in early September and it was so perfect. We walked around EVERYWHERE, so there is no way I'd want to do that in the winter.I have also been a few times in June, which was beautiful as well. I'd definitely hold out for the spring. Flight prices could change, too. Looking at spring airfare right now is at least 6+ months in advance, which always seems to be more expensive. Keep an eye on the airfare, and you could probably get a good deal. We're obviously closer, but we only paid like $130 roundtrip from Buffalo for September. And check out Priceline for hotels. We got a great one for $75/night.

SarahBethBR

Thanks for the advice everybody!  I think we'll either do spring or early fall.That is if we go.  Brett just called and mentioned that he would like to go somewhere in Europe if I didn't mind.  OF COURSE I DON'T MIND!