Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
ORD > San Salvador, El Salvador: Biz from $743 Econ from $178. – Apr-Jun
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Philadelphia, Pennsylvania: Econ from $48. – Apr-Jun
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Dallas, Texas: Biz from $429 Econ from $51. – Apr-Jun
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Cali, Colombia: Biz from $939 Econ from $264. – Apr-Jun
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Charlotte, North Carolina: Biz from $387 Econ from $60. – Apr-Jun
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
MDW > Ontario, California: Econ from $89. – Apr-Jun
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
ORD > Montego Bay, Jamaica: Econ from $913. – Apr-Jun
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > San Antonio, Texas: Econ from $99. – Apr-Jun
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Baltimore, Maryland: Econ from $61. – Apr-Jun
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Port Au Prince, Haiti: Biz from $882 Econ from $377. – Apr-Jun
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Phoenix, Arizona: Econ from $68. – Apr-Jun
If you ever go to Phoenix, consider staying in Scottsdale. It’s a really cute town slightly North of Phoenix, away…
ORD > Guatemala City, Guatemala: Biz from $854 Econ from $176. – Apr-Jun
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 $900. Econ from $198. – Apr-Jun
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Atlanta, Georgia: Biz from $409. Econ from $39. – Apr-Jun
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Santo Domingo, Dominican Republic: Biz from $836. Econ from $217. – Apr-Jun
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > San Diego, California: Econ from $86. – Apr-Jun
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Kingston, Jamaica: Biz from $814 Econ from $259. – Apr-Jun
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Sacramento, California: Econ from $101. – Apr-Jun
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
ORD > Nashville, Tennessee: Biz from $328. Econ from $48. – May-Jul (Including Summer Break)
If you like live music, you’ve got to check out Nashville. We visited Broadway street every night we were there,…
MDW > Guatemala City, Guatemala: Econ from $158. – Apr-Jun
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Cincinnati, Ohio: Biz from $416 Econ from $117. – Apr-Jun
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Fort Lauderdale, Florida: Econ from $66. – Apr-Jun
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
MDW > Punta Cana, Dominican Republic: Biz from $923 Econ from $233. – Apr-Jun
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Santa Ana, California: Econ from $129. – Apr-Jun
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
MDW > Oranjestad, Aruba: Econ from $263. – Apr-Jun
Our trip to Aruba was the beginning of JGOOT. I stumbled across ridiculously cheap flights, bundled that with quite a…
MDW > Boston, Massachusetts: Biz from $459 Econ from $101. – Apr-Jun
I rarely post trips to Boston because they are typically so expensive and I advise using points instead of paying…
ORD > Buenos Aires, Argentina: Biz from $2596 Econ from $742. – 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 > Seattle, Washington: Biz from $499 Econ from $117. – Apr-Jun
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
MDW > Raleigh, North Carolina: Econ from $50. – Apr-Jun
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
MDW > San Jose, Costa Rica: Biz from $1276 Econ from $198. – Apr-Jun
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Salt Lake City, Utah: Econ from $95. – Apr-Jun
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
MDW > Houston, Texas: Econ from $68. – Apr-Jun
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Managua, Nicaragua: Biz from $931 Econ from $241. – Apr-Jun
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Richmond, Virginia: Biz from $407 Econ from $125. – Apr-Jun
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
MDW > Panama City, Panama: Biz from $914 Econ from $446. – Apr-Jun
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
MDW > Bogota, Colombia: Biz from $783 Econ from $314. – Apr-Jun
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Los Angeles, California: Econ from $94. – Apr-Jun
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
MDW > Dallas, Texas: Econ from $63. – Apr-Jun (Including Summer Break)
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Cartagena, Colombia: Biz from $977 Econ from $266. – Apr-Jun
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…