Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Bogota, Colombia: Biz from $724 Econ from $167. – 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 > Los Angeles, California: Econ from $56. – Sep-Nov (Including Fall Break) [SOLD OUT]
Be sure to check out the “cruises” links below to see if you could grab this cheap flight, and hop…
ORD > Dallas, Texas: Biz from $409 Econ from $52. – Oct-Dec [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Fort Lauderdale, Florida: Econ from $40. – 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 > San Jose, Costa Rica: Biz from $799 Econ from $172. – 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 > Budapest, Hungary: Biz from $1,735 Econ from $297. – Oct-Dec [SOLD OUT]
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Oakland, California: Econ from $72. – Oct-Dec [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Atlanta, Georgia: Biz from $325 Econ from $42. – Oct-Dec [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > San Diego, California: Econ from $50. – 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…
ORD > Beirut, Lebanon: Econ from $523. – Oct-Dec (Including Fall Break) [SOLD OUT]
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Cali, Colombia: Biz from $1,000 Econ from $165. – Oct-Dec [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Panama City, Panama: Biz from $900 Econ from $185. – 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 > Memphis, Tennessee: Biz from $313 Econ from $133. – 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…
ORD > Dayton, Ohio: Biz from $333 Econ from $128. – 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 > Des Moines, Iowa: Biz from $313 Econ from $133. – Oct-Dec [SOLD OUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Fairbanks, Alaska: Biz from $986 Econ from $320. – Oct-Dec (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 > Port Au Prince, Haiti: Biz from $1,015 Econ from $177. – Oct-Dec [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Manchester, New Hampshire: Biz from $587 Econ from $95. – 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 > Seattle, Washington: Biz from $604 Econ from $80. – 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 > San Jose del Cabo, Mexico: Biz from $769 Econ from $212. – Sep-Nov [SOLD OUT]
When you go to Cabo, you’ll get approached by dozens of locals offering the best deals possible for snorkeling, sailing,…
ORD > Malaga, Spain: Econ from $382. – 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 > New York, New York: Biz from $347 Econ from $75. – Sep-Nov [SOLD OUT]
Have you ever booked a cruise only to find out that the flight to get there was going to be…
ORD > Fort Myers, Florida: Econ from $39. – 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 > San Pedro Sula, Honduras: Biz from $631 Econ from $177. – 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 > Moscow, Russia: Biz from $1,857 Econ from $485. – Oct-Dec (Including Fall Break) [SOLD OUT]
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Philadelphia, Pennsylvania: Biz from $313 Econ from $75. – 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 > Denver, Colorado: Biz from $415 Econ from $65. – Sep-Nov (Including Fall Break) [SOLD OUT]
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Merida, Mexico: Biz from $675 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.…
ORD > Split, Croatia: Biz from $2,335 Econ from $515. – 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…
ORD > Richmond, Virginia: Biz from $445 Econ from $79. – Sep-Nov [SOLD OUT]
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
MDW > Savannah, Georgia: Biz from $515 Econ from $65. – 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 $615 Econ from $174. – 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 > Charlotte, North Carolina: Econ from $66. – 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 > Dallas, Texas: Biz from $376 Econ from $57. – 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 > Odessa, Ukraine: Biz from $1,732 Econ from $491. – Sep-Nov (Including Fall Break) [SOLD OUT]
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > New Orleans, Louisiana: Biz from $415 Econ from $41. – Sep-Nov [SOLD OUT]
Have you ever booked a cruise only to find out that the flight to get there was going to be…
ORD > Pristina, Kosovo: Econ from $494. – Sep-Nov [SOLD OUT]
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Bari, Italy: Econ from $442. – 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 > Los Angeles, California: Econ from $53. – Sep-Nov (Including Fall Break) [SOLD OUT]
Be sure to check out the “cruises” links below to see if you could grab this cheap flight, and hop…