In the weather sense? Things usually start cooling off abruptly around the end of October. posted by thomas j wise at 10:09 AM on February 23, 2011
Yes. It might be chilly, but it's beautiful. And there's plenty to do here, no matter what you're into. posted by phunniemee at 10:13 AM on February 23, 2011
It could be pretty cold (probably in the 40s but maybe warmer). But it (almost certainly) won't be snowing, and Chicago is pretty in the fall and not full of tourists. posted by geegollygosh at 10:30 AM on February 23, 2011
Why the hell not? It'll be crisp and easy to walk around, and Chicago is a great city at any time of the year -- even in grody winter slush.
Pack a few layers; the temperature can change dramatically in one day. Even on warm fall days, the mornings can be colder than expected.
Chicago is so nicely compact, though, that you'll be able to duck in and out of someplace warm no matter what. posted by Madamina at 10:37 AM on February 23, 2011
Why wouldn't it be? (Well, unless you're the type who wants an outdoor laze-about-in-the-sun honeymoon, in which case you shouldn't be considering any northern city in October.) You're unlikely to get stormed in (or out), and there's so much to do that if the weather is crappy you can do museums/etc; and if it's nice you can do zoos/tours. Bring appropriate clothing (include rain gear!) and you'll be fine. posted by jlkr at 11:05 AM on February 23, 2011
This is an excellent time to be in Chicago- it stays relatively dry, and about this time you start to get nice crisp fall days with really amazing afternoon light. posted by TheWhiteSkull at 12:03 PM on February 23, 2011 [1 favorite]
October is probably the most reliably comfortable time of the year here. In June or July you're risking heat waves or thunderstorms, but October is thoroughly dry, crisp, and beautiful. posted by theodolite at 12:40 PM on February 23, 2011
Late October as in near Halloween? Maybe not so dry -- it frequently rains on or near Halloween here, and the temperature fluctuates greatly at that time of year. Late September/early October would be more reliable. posted by me3dia at 1:33 PM on February 23, 2011
I've lived in Chicago for most of my 40 years. I don't think it's a good idea weather-wise.
All of September and probably up to October 15th the weather is fantastic. After that it can get really cold and/or rain a lot. My wedding was at the very end of October eight years back and it was in the 20s F.
This last year we had really nice weather through mid November, and Halloween was actually warm. But you're really rolling the dice weather-wise. posted by jeff-o-matic at 2:32 PM on February 23, 2011
My parents always visit us in Chicago in October (from Atlanta) because of how nice our fall weather can be...it's crisp but not cold and the leaves are pretty. I recommend the Frank Lloyd Wright home and Studio tour in October; it seems to fit the season well. Also, as asuprenant said, we do cozy really well. I like restaurants like Nightwood, Lula, and Publican, (other threads have lots of other ideas) for seasonal menus. posted by shrimpsmalls at 9:04 PM on February 23, 2011
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posted by thomas j wise at 10:09 AM on February 23, 2011