Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
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 > Barranquilla, Colombia: Biz from $565 Econ from $313.- Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
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 > Budapest, Hungary: Econ from $422.- 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 > 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 > Denver, Colorado: Biz from $438 Econ from $107.- Jan-Mar
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Madrid, Spain: Econ from $372.- Apr-Jun
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Brasilia, Brazil: Biz from $2056 Econ from $569.- Jan-Mar [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 > Kochi, India: Econ from $759. – Apr-Jun
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
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 > New York, New York: Biz from $205 Econ from $72. – Jan-Mar
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
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 > Norfolk, Virginia: Econ from $126.- Dec-Feb [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 > Cincinnati, Ohio: Biz from $363 Econ from $152.- Jan-Mar
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
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 > Belgrade, Serbia: Econ from $515.- Apr-Jun
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Bogota, Colombia: Biz from $561 Econ from $236.- Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Austin, Texas: Biz from $359 Econ from $66.- 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 > 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 > Gdansk, Poland: Econ from $438.- Feb-Apr (Including Spring Break)
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 > Las Vegas, Nevada: Biz from $344 Econ from $91. – Jan-Mar
Grab this flight and spend the savings on several shows. (I highly recommend the Michael Jackson show, as well as…
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 > Poznan, Poland: Econ from $477. – Mar-May
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
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.
MDW > Knoxville, Tennessee: Econ from $167. – Jun-Aug (Including Fourth of July and Summer Break)
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Asheville, North Carolina: Biz from $411 Econ from $164. – Jan-Mar (Presidents day Weekend)
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
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 > Baltimore, Maryland: Biz from $269 Econ from $58.- Jan-Mar
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
ORD > San Diego, California: Econ from $122.- Jan-Mar
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Riga, Latvia: Econ from $509.- Jan-Mar [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 > 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 > Philadelphia, Pennsylvania: Biz from $283 Econ from $78.- Jan-Mar
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
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…