With two major airports within the Chicago area (O'Hare and Midway), it is easy to find flights from anywhere in the country on sale. Get a City Pass, and you will be able to see some of the major sites in the city, including the Art Institute, the Shedd Aquarium, the Field Natural History Museum, Skydeck Chicago, The Adler Planetarium , etc. at a hugely discounted rate. Don't forget about Millenium Park, Navy Pier, and the great jazz clubs too. If blues music is your thing, head on over to Rush Street. The views from Lake Michigan are free, as is window shopping on the miracle mile. Whatever you would like to do, whether it involves nature, culture, or some awesome international cuisine, Chicago is the stop for you.