Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Montego Bay, Jamaica: Biz from $522 Econ from $243.- Sep-Nov [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > San Diego, California: Econ from $154. – Oct-Dec [SOLD OUT]
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
MDW > Jacksonville, Florida: Econ from $142. – Aug-Oct [SOLD OUT]
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
MDW > Newark, New Jersey: Econ from $105. – Oct-Dec [SOLD OUT]
Be sure to check out the “cruises” link below to see if you could take advantage of this cheap flight,…
ORD > Denver, Colorado: Biz from $412 Econ from $104. – Sep-Nov [SOLD OUT]
If you visit Denver, be sure to drop me a note. I moved here from California 25 years ago, and…