Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Larnaca, Cyprus: Econ from $550. – Mar-May
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Los Angeles, California: Biz from $468 Econ from $144. – Feb-Apr
Have you ever booked a cruise only to find out that the flight to get there was going to be…
ORD > Florianopolis, Brazil: Biz from $1350 Econ from $738. – Nov-Jan (Including Thanksgiving)
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Bali, Indonesia: Econ from $671. – 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 > Mykonos, Greece: Econ from $598. – Jul-Sep
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Punta Cana, Dominican Republic: Biz from $807 Econ from $215. – Feb-Apr (Including Spring Break)
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 $331 Econ from $116.- Jan-Mar [SOLD OUT]
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > George Town, Cayman Islands: Biz from $488 Econ from $219.- 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 > Jakarta, Indonesia: Econ from $697. – 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 > Malaga, Spain: Econ from $393. – Mar-May
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 $543 Econ from $267.- 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 > Cancun, Mexico: Biz from $398 Econ from $202.- Jan-Mar
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Riga, Latvia: Econ from $420.- 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 > San Salvador, El Salvador: Biz from $472 Econ from $174.- Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Liberia, Costa Rica: Biz from $1166 Econ from $341. – Mar-May (Including Spring Break)
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 > Georgetown, Guyana: Biz from $789 Econ from $412. – Jan-Mar
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Atlantic City, New Jersey: Biz from $467 Econ from $146. – Jan-Mar [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
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 > Jacksonville, Florida: Biz from $577 Econ from $150.- Dec-Feb [SOLD OUT]
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
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 > Fort Myers, Florida: Biz from $315 Econ from $57.- Feb-Apr
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
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 –…