Round-trip flight to London, $162, STA Travel
I didn't discover STA Travel until I was in business school, and once I did I felt like kicking myself. What are all these fantastic deals?!? And I was almost at the end of my scholastic career. And now STA Travel has weekly deals to the sorts of places that you and I want to go -- for amazing deals.
London in the winter may not be the best place for a tan, but it's fantastic if you're into art, theatre, shopping, funky culture, Indian food ... my tongue is watering at the memory of those amazing raitas at Rasa. Ready to go yet? STA Travel's weekly deal will take you to London (and back!) any time between now and March for $162 from Chicago ; $169 from Boston and New York, and $188 from L.A. The cheapest I could find a similar ticket on Orbitz was $245 for Chicago to London (still a great deal, by the way!) for a week picked at random from among STA's travel dates.