When I went to Costa Rica, I flew into Liberia. Nothing special there, but you’re only about a half-hour from…
ORD > Dubai, United Arab Emirates: Econ from $618. – Feb-Apr (Including Spring Break)
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Managua, Nicaragua: Biz from $469 Econ from $212. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Boracay, Philippines: Econ from $1083. – Jan-Mar
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
MDW > San Juan, Puerto Rico: Biz from $406 Econ from $178. – Jan-Mar (Presidents day Weekend)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > San Pedro Sula, Honduras: Biz from $446 Econ from $213.- Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Colombo, Sri Lanka: Econ from $865. – Feb-Apr (Including Spring Break)
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Cozumel, Mexico: Biz from $1028 Econ from $323. – Feb-Apr (Including Spring Break)
Cozumel is a completely separate part of mexico, and if you’ve ever thought about scuba diving, there isn’t a more…
ORD > Lisbon, Portugal: Econ from $432.- Jan-Mar
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Cartagena, Colombia: Biz from $606 Econ from $238.- Feb-Apr
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Fort Lauderdale, Florida: Biz from $272 Econ from $58.- Jan-Mar
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Luqa, Malta: Econ from $519. – Jan-Mar
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Miami, Florida: Biz from $236 Econ from $66. – Jan-Mar
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Guatemala City, Guatemala: Biz from $657 Econ from $208. – Mar-May
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Larnaca, Cyprus: Econ from $585.- Mar-May
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Oranjestad, Aruba: Biz from $474 Econ from $223.- Dec-Feb [SOLD OUT]
Our trip to Aruba was the beginning of JGOOT. I stumbled across ridiculously cheap flights, bundled that with quite a…
ORD > Palanga, Lithuania: Econ from $436.- Jan-Mar (Presidents day Weekend)
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Los Angeles, California: Econ from $124. – Jan-Mar (Presidents day Weekend)
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Bali, Indonesia: Econ from $668. – Feb-Apr
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Punta Cana, Dominican Republic: Biz from $871 Econ from $219. – Apr-Jun (Including Summer Break)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Mykonos, Greece: Econ from $701. – Jul-Sep
Be sure to check the flight plus hotel price below! Sometimes, you can get your hotel for nearly free –…
ORD > Belize City, Belize: Biz from $859 Econ from $321. – Feb-Apr
* This is a “fare dump” with a few alternate dates available.
ORD > Florianopolis, Brazil: Econ from $716. – Feb-Apr (Including Spring Break)
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Malaga, Spain: Econ from $416.- Feb-Apr
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Montego Bay, Jamaica: Biz from $531 Econ from $278.- Jan-Mar (Presidents day Weekend)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Boston, Massachusetts: Biz from $287 Econ from $117.- Jan-Mar
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Cancun, Mexico: Biz from $455 Econ from $196.- Feb-Apr
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > George Town, Cayman Islands: Biz from $461 Econ from $247. – Dec-Feb [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Barcelona, Spain: Econ from $492. – Feb-Apr
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > San Jose, Costa Rica: Biz from $588 Econ from $237. – Feb-Apr
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Managua, Nicaragua: Biz from $456 Econ from $211. – Jan-Mar (Presidents day Weekend)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > San Juan, Puerto Rico: Econ from $176.- Jan-Mar [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > San Pedro Sula, Honduras: Biz from $490 Econ from $214.- Dec-Feb [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Dubai, United Arab Emirates: Econ from $730.- Jan-Mar (Presidents day Weekend)
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > San Salvador, El Salvador: Biz from $402 Econ from $180.- Dec-Feb [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Boracay, Philippines: Econ from $855. – Aug-Oct
Have I mentioned that the Philippines has some of the best diving in the world? The beaches are amazing too.…
ORD > Fort Lauderdale, Florida: Biz from $278 Econ from $64. – Dec-Feb (Including MLK Weekend) [SOLD OUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Cozumel, Mexico: Biz from $1125 Econ from $332. – Feb-Apr (Including Spring Break)
Cozumel is a completely separate part of mexico, and if you’ve ever thought about scuba diving, there isn’t a more…
MDW > Lisbon, Portugal: Econ from $501.- Jan-Mar (Presidents day Weekend)
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Kingston, Jamaica: Biz from $650 Econ from $337.- Jan-Mar [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…