Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Dubrovnik, Croatia: Biz from $2622 Econ from $600. – Sep-Nov
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
ORD > Thera, Greece: Econ from $698. – Sep-Nov
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Mykonos, Greece: Econ from $655. – Sep-Nov (Including Fall Break)
Be sure to check the flight plus hotel price below! Sometimes, you can get your hotel for nearly free –…
ORD > Thera, Greece: Econ from $620. – Sep-Nov
Be sure to check the flight plus hotel price below! Sometimes, you can get your hotel for nearly free –…
MDW > Dallas, Texas: Biz from $448 Econ from $40. – Oct-Dec [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
MDW > Jacksonville, Florida: Biz from $560 Econ from $118. – Oct-Dec [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
MDW > Boston, Massachusetts: Biz from $418 Econ from $78. – 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 > Kinshasa, Democratic Republic of the Congo: Econ from $847. – Oct-Dec [SOLD OUT]
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
MDW > Santa Ana, California: Econ from $104. – 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 > Algiers, Algeria: Econ from $673. – Oct-Dec [SOLD OUT]
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
MDW > San Pedro Sula, Honduras: Biz from $951 Econ from $224. – 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 > Oakland, California: Econ from $83. – 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 > Kingston, Jamaica: Biz from $940 Econ from $282. – 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 > Cartagena, Colombia: Biz from $924 Econ from $226. – 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 > Palanga, Lithuania: Econ from $412. – 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…
MDW > Sacramento, California: Econ from $116. – 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…
RD > Fortaleza, Brazil: Econ from $638. – Sep-Nov (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 > Washington, DC: Econ from $69. – Oct-Dec [SOLD OUT]
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
ORD > Iasi, Romania: Econ from $550. – 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…
MDW > Boise, Idaho: Biz from $692 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 > San Diego, California: Econ from $88. – 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 > Philadelphia, Pennsylvania: Biz from $378 Econ from $40. – 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 > Guatemala City, Guatemala: Econ from $199. – Oct-Dec (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 > Atlantic City, New Jersey: Biz from $590 Econ from $96. – 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 > Cincinnati, Ohio: Biz from $318 Econ from $90. – 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 > Abuja, Nigeria: Biz from $3413 Econ from $923. – 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 > Kansas City, Kansas: Biz from $380 Econ from $153. – 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 > Bogota, Colombia: Biz from $858 Econ from $287. – 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 > Georgetown, Guyana: Biz from $1292 Econ from $462. – Sep-Nov (Including Fall Break) [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > San Jose, California: Econ from $112. – 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: Econ from $122. – 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 > San Francisco, California: Econ from $60. – Sep-Nov [SOLD OUT]
Beaches, Sunsets, Redwoods, Golden Gate Bridge, fine dining, night life, Lombard Street, & cable cars… San Francisco is one of…
ORD > Toluca, Mexico: Econ from $240. – 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 > Salt Lake City, Utah: Econ from $88. – 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 > Armenia, Colombia: Econ from $257. – 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 > Tunis, Tunisia: Econ from $774. – 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…
MDW > Raleigh, North Carolina: Biz from $378 Econ from $40. – Sep-Nov (Including Fall Break) [SOLD OUT]
3 different flights to/from Raleigh – All under $100 round-trip. * This is a “fare dump” with a few alternate…
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 > Santa Ana, California: Econ from $100. – 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…