Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Fort Myers, Florida: Econ from $38. – Sep-Nov (Including Fall Break) [SOLD OUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Cali, Colombia: Biz from $972 Econ from $161. – Sep-Nov (Including Fall Break) [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Fairbanks, Alaska: Biz from $895 Econ from $314. – Sep-Nov [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Denver, Colorado: Biz from $415 Econ from $64. – Oct-Dec [SOLD OUT]
If you visit Denver, be sure to drop me a note. I moved here from California 25 years ago, and…
ORD > Fort Lauderdale, Florida: Econ from $38. – Sep-Nov [SOLD OUT]
Be sure to check out the “cruises” link below to see if you could take advantage of this cheap flight,…
ORD > San Juan, Puerto Rico: Biz from $501 Econ from $86. – Sep-Nov (Including Fall Break) [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Seattle, Washington: Biz from $613 Econ from $126. – Sep-Nov [SOLD OUT]
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Philadelphia, Pennsylvania: Biz from $345 Econ from $74. – Sep-Nov [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Myrtle Beach, South Carolina: Biz from $445 Econ from $60. – Sep-Nov [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Oranjestad, Aruba: Biz from $1,035 Econ from $225. – Sep-Nov [SOLD OUT]
When we went to Aruba – we stayed at the Renaissance, and it was fantastic. They have their own private…
ORD > Bilbao, Spain: Econ from $464. – Oct-Dec [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Los Angeles, California: Econ from $60. – Sep-Nov [SOLD OUT]
Be sure to check out the “cruises” links below to see if you could grab this cheap flight, and hop…
ORD > New Orleans, Louisiana: Biz from $399 Econ from $60. – Sep-Nov [SOLD OUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > San Salvador, El Salvador: Biz from $695 Econ from $183. – Sep-Nov (Including Fall Break) [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Savannah, Georgia: Biz from $611 Econ from $65. – Sep-Nov (Including Fall Break) [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Boston, Massachusetts: Biz from $429 Econ from $63. – Sep-Nov [SOLD OUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Bogota, Colombia: Biz from $781 Econ from $192. – 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.…
ORD > Abu Dhabi, United Arab Emirates: Econ from $572. – Sep-Nov [SOLD OUT]
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Madrid, Spain: Econ from $380. – Sep-Nov [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Colorado Springs, Colorado: Biz from $448 Econ from $142. – Sep-Nov (Including Fall Break) [SOLD OUT]
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
ORD > Santiago de los Caballeros, Dominican Republic: Biz from $911 Econ from $230. – 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.…
ORD > Casablanca, Morocco: Econ from $583. – Sep-Nov [SOLD OUT]
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Porto, Portugal: Econ from $497. – Sep-Nov (Including Fall Break) [SOLD OUT]
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Manchester, New Hampshire: Biz from $419 Econ from $119. – Sep-Nov (Including Fall Break) [SOLD OUT]
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Portland, Oregon: Biz from $619 Econ from $95. – Sep-Nov [SOLD OUT]
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
ORD > Palma de Mallorca, Spain: Econ from $498. – Sep-Nov [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Des Moines, Iowa: Biz from $313 Econ from $133. – Sep-Nov (Including Fall Break) [SOLD OUT]
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
ORD > Managua, Nicaragua: Biz from $1,040 Econ from $352. – 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.…
ORD > Dubai, United Arab Emirates: Econ from $586. – Sep-Nov [SOLD OUT]
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Honolulu, Hawaii: Econ from $358. – Sep-Nov [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Cedar Rapids, Iowa: Econ from $133. – Sep-Nov [SOLD OUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
MDW > Atlanta, Georgia: Biz from $437 Econ from $117. – Oct-Dec [SOLD OUT]
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
ORD > Cozumel, Mexico: Biz from $701 Econ from $223. – Sep-Nov [SOLD OUT]
Cozumel is a completely separate part of mexico, and if you’ve ever thought about scuba diving, there isn’t a more…
MDW > Barcelona, Spain: Econ from $511. – Sep-Nov [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Peoria, Arizona: Biz from $349 Econ from $89. – Sep-Nov [SOLD OUT]
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
ORD > Burlington, Kentucky: Econ from $73. – Sep-Nov [SOLD OUT]
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Guatemala City, Guatemala: Biz from $695 Econ from $186. – Sep-Nov (Including Fall Break) [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Rome, Italy: Econ from $402. – Sep-Nov [SOLD OUT]
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Budapest, Hungary: Biz from $1,745 Econ from $561. – Sep-Nov [SOLD OUT]
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…