Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Budapest, Hungary: Econ from $506. – 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 > Venice, Italy: Econ from $491. – 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 > Sarajevo, Bosnia and Herzegovina: Econ from $614. – 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 > Athens, Greece: Econ from $487. – 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 > Simpson Bay, St. Maarten: Econ from $364. – 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 > Mumbai, India: Econ from $611. – 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 > Entebbe, Uganda: 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 > Warsaw, Poland: Econ from $471. – 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 > Tunis, Tunisia: Biz from $2,592 Econ from $721. – 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 > Nashville, Tennessee: Biz from $370 Econ from $118. – Sep-Nov (Including Fall Break) [SOLD OUT]
If you like live music, you’ve got to check out Nashville. We visited Broadway street every night we were there,…
ORD > Abuja, Nigeria: Biz from $2,774 Econ from $759. – Sep-Nov [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 > Cancun, Mexico: Biz from $936 Econ from $194. – 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 > Tallinn, Estonia: Econ from $471. – Sep-Nov [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 > Nairobi, Kenya: Econ from $644. – Sep-Nov (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 > Bucharest, Romania: Econ from $450. – 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 > Monterrey, Mexico: 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 > Riga, Latvia: Econ from $411. – 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 > Alicante, Spain: Econ from $429. – 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 > Colorado Springs, Colorado: Biz from $566 Econ from $168. – Oct-Dec [SOLD OUT]
Four words if you visit Colorado Springs: Garden of the gods. * This is an airline sale that is time-sensitive.…
ORD > Fort Lauderdale, Florida: Econ from $91. – 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…
MDW > Lima, Peru: Econ from $343. – 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 > Boston, Massachusetts: Biz from $438 Econ from $144. – 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 > Tirana, Albania: Econ from $577. – 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 > Houston, Texas: Econ from $180. – 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 > Guayaquil, Ecuador: Biz from $916 Econ from $367. – Sep-Nov (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 > Reykjavik, Iceland: Econ from $569. – 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 > Sarajevo, Bosnia and Herzegovina: Econ from $592. – 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 > Hamburg, Germany: Econ from $472. – 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 > Simpson Bay, St. Maarten: Econ from $414. – 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 > Torreon, Mexico: Econ from $254. – 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 > Boston, Massachusetts: Biz from $438 Econ from $150. – 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 > Hartford, Connecticut: Biz from $596 Econ from $176. – 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 > Krakow, Poland: Econ from $414. – 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 > Quito, Ecuador: Biz from $879 Econ from $355. – Sep-Nov (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 > Lisbon, Portugal: Econ from $365. – 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 > Peoria, Arizona: Econ from $168. – 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…
MDW > Knoxville, Tennessee: Econ from $42. – 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 > Naples, Italy: Econ from $425. – 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 > Oranjestad, Aruba: Econ from $459. – Sep-Nov (Including Fall Break) [SOLD OUT]
When we went to Aruba – we stayed at the Renaissance, and it was fantastic. They have their own private…