Normally I'm all about staying in Chicago for the summer because we live in the most beautiful city in the world when the weather's gorgeous. After the last month or two of schizophrenic weather, it's time to think about going somewhere warm and sunny. American, Continental and United are showing round trip airfares in September onwards for $441 all-in.
But Nick! you say - I'm cold NOW! well yes, but the weather will get better. However, when winter rolls around and we're faced with the threat of another snowpocalypse, it's best to go somewhere warm. Even when it's in the high 70's in Hawaii, you're still in Hawaii.