Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Lisbon, Portugal: Econ from $389.- Oct-Dec
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
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
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…
ORD > Kathmandu, Nepal: Econ from $744. – Feb-Apr
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Palma de Mallorca, Spain: Econ from $414. – Feb-Apr (Including Spring Break)
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Liberia, Costa Rica: Biz from $1190 Econ from $369. – Nov-Jan
When I went to Costa Rica, I flew into Liberia. Nothing special there, but you’re only about a half-hour from…
ORD > Mexico City, Mexico: Econ from $238. – Sep-Nov (Including Fall Break) [SOLD OUT]
Although I’ve been to about half a dozen cities in Mexico, Mexico City isn’t one of them. Several of my…
ORD > Innsbruck, Austria: Econ from $551. – Jan-Mar (Presidents day Weekend)
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
MDW > Newark, New Jersey: Econ from $105. – Oct-Dec
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…
ORD > Dubrovnik, Croatia: Econ from $625. – Sep-Nov (Including Fall Break) [SOLD OUT]
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…