Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Dubrovnik, Croatia: Econ from $581. – May-Jul (Including Summer 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 > Hartford, Connecticut: Biz from $498 Econ from $138. – May-Jul (Including Summer 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…
IAH > Calgary, Canada: Econ from $281. – May-Jul (Including Summer 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 > Springfield, Massachusetts: Econ from $148. – May-Jul (Including Summer Break) [SOLD OUT]
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
ORD > Decatur, Georgia: Econ from $161. – Apr-Jun (Including Summer Break)
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
ORD > Ljubljana, Slovenia: Econ from $572. – Apr-Jun (Including Summer Break)
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Lisbon, Portugal: Econ from $392. – May-Jul (Including Summer 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 > Miami, Florida: Econ from $57. – May-Jul (Including Summer 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 > Tirana, Albania: Biz from $2,672 Econ from $552. – Apr-Jun (Including Summer Break)
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Chisinau, Moldova: Econ from $485. – Apr-Jun (Including Summer Break)
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
MDW > Ottawa, Canada: Econ from $203. – May-Jul (Including Summer 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 > Tbilisi, Georgia: Econ from $583. – Apr-Jun (Including Summer Break)
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Riga, Latvia: Econ from $461. – Jul-Sep (Including Summer Break) [SOLDOUT]
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Watertown, Massachusetts: Econ from $127. – May-Jul (Including Summer 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 > Brussels, Belgium: Econ from $370. – May-Jul (Including Summer Break) [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Ketchikan, Alaska: Econ from $362. – May-Jul (Including Summer Break) [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Juneau, Alaska: Econ from $316. – May-Jul (Including Summer Break) [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Louisville, Kentucky: Biz from $338 Econ from $118. – May-Jul (Including Summer Break) [SOLD OUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse search…
ORD > Washington, DC: Econ from $148. – May-Jul (Including Summer Break) [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
MDW > Asheville, North Carolina: Econ from $88. – May-Jul (Including Summer Break) [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
MDW > Savannah, Georgia: Econ from $104. – May-Jul (Including Summer Break) [SOLD OUT]
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
ORD > Bilbao, Spain: Econ from $414. – Apr-Jun (Including Summer Break)
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
MDW > Zagreb, Croatia: Econ from $502. – Apr-Jun (Including Summer Break)
* There only appear to be a few seats at this price and availability is spotty. It will take a…
MDW > Halifax, Canada: Econ from $253. – Jul-Sep (Including Summer Break) [SOLDOUT]
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
MDW > Toronto, Canada: Econ from $252. – May-Jul (Including Summer 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 > Puerto Escondido, Mexico: Econ from $210. – May-Jul (Including Summer 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 > Sitka, Alaska: Econ from $392. – May-Jul (Including Summer Break) [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
MDW > Atlanta, Georgia: Biz from $483 Econ from $58. – May-Jul (Including Summer 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 > Marrakesh, Morocco: Biz from $2,138 Econ from $417. – Apr-Jun (Including Summer Break)
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Palanga, Lithuania: Econ from $548. – May-Jul (Including Summer 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 $393. – May-Jul (Including Summer 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 > Burlington, Kentucky: Econ from $104. – Jun-Aug (Including Summer Break) [SOLDOUT]
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 $391. – Apr-Jun (Including Summer Break)
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Cairo, Egypt: Econ from $570. – Apr-Jun (Including Summer Break)
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Fairbanks, Alaska: Biz from $885 Econ from $338. – May-Jul (Including Summer Break) [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Sitka, Alaska: Biz from $970 Econ from $329. – May-Jul (Including Summer 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 > Puerto Escondido, Mexico: Econ from $210. – May-Jul (Including Summer 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 > Ketchikan, Alaska: Biz from $905 Econ from $347. – Jul-Sep (Including Summer Break) [SOLDOUT]
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Dubrovnik, Croatia: Biz from $2,334 Econ from $573. – May-Jul (Including Summer Break) [SOLD OUT]
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…