Chicago

According to Brian Ek (also known as "The Travel Ekspert") of Priceline, 2012 is the year to see the Windy City on the cheap during summer. Writes Ek, "The average summer airfare to O'Hare is $339 (down 4.4 percent vs. last year), while Midway is an even more affordable $305." Ek also spotted several discounted prices for Chicago stays, including cheap rates (as low as $163 per night) at Hotel 71, a downtown Chicago property with high ratings on Priceline.

To double the discounts, bundle hotel and airfare together with an all-around affordable vacation package. Packages often offer an easy way to save on travel, and they also simplify the trip-planning process. We found a weeklong package on Southwest Vacations, including round-trip airfare from New York, at Hotel Lincoln for $1,258 (including all taxes and fees, from July 11 through 18). Hotel Lincoln is located in Chicago's North Side and has a four-and-a-half rating (out of five) on our sister site TripAdvisor.

We also spotted weeklong Southwest Vacations packages as cheap as $529 per person, but the hotels featured in these exceedingly economical trips were located a ways outside of Chicago. Still, the savings are considerable. If you're willing to travel a bit to get into the city, you can plan a seven-night Chicago escape for two for just over $1,000.