Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Oranjestad, Aruba: Biz from $1061 Econ from $285. – Apr-Jun (Including Summer Break)
Our trip to Aruba was the beginning of JGOOT. I stumbled across ridiculously cheap flights, bundled that with quite a…
ORD > Boston, Massachusetts: Biz from $417 Econ from $74. – May-Jul (Including Summer Break)
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
MDW > Savannah, Georgia: Biz from $630 Econ from $75. – Apr-Jun (Including Summer Break)
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Reno, Nevada: Econ from $149. – Apr-Jun (Including Summer Break)
Whether boating in the summer, skiing in the winter, hiking to take in the beautiful scenery, or gambling at the…
ORD > Cincinnati, Ohio: Biz from $264 Econ from $119. – May-Jul (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 > Managua, Nicaragua: Biz from $933 Econ from $192. – 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 > Piarco, Trinidad and Tobago: Biz from $899 Econ from $427. – May-Jul (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 > Portland, Oregon: Econ from $107. – May-Jul (Including Summer Break)
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
MDW > Knoxville, Tennessee: Econ from $79. – May-Jul (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…
(Including Summer Break) ORD > Belo Horizonte, Brazil: Econ from $643. – May-Jul
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
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 > 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…
MDW > Christiansted, U.S. Virgin Islands: Econ from $342. – May-Jul (Including Summer Break)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Baltimore, Maryland: Econ from $78. – May-Jul (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…
MDW > Buenos Aires, Argentina: Econ from $858. – 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…
ORD > Thiruvananthapuram, India: Econ from $811. – 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 > Savannah, Georgia: Biz from $587 Econ from $131. – Jul-Sep (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…
MDW > Raleigh, North Carolina: Econ from $80. – Jul-Sep (Including Summer Break) [SOLD OUT]
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Saint Thomas Island, U.S. Virgin Islands: Econ from $214. – Jul-Sep (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 > Atlantic City, New Jersey: Biz from $622 Econ from $126. – Jul-Sep (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 > Lexington, Kentucky: Biz from $328 Econ from $148. – Jul-Sep (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…
MDW > Asheville, North Carolina: Econ from $92. – Jun-Aug (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…
ORD > Atlanta, Georgia: Biz from $398 Econ from $45. – Jul-Sep (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 > Managua, Nicaragua: Biz from $1147 Econ from $291. – Jul-Sep (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 > Cincinnati, Ohio: Biz from $368 Econ from $170. – Jul-Sep (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 > San Pedro Sula, Honduras: Biz from $791 Econ from $302. – Jul-Sep (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 > Christiansted, U.S. Virgin Islands: Econ from $294. – Jun-Aug (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 > Madison, Wisconsin: Biz from $298 Econ from $138. – Jul-Sep (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…
MDW > Houston, Texas: Econ from $119. – Jul-Sep (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…
MDW > Savannah, Georgia: Econ from $78. – Jun-Aug (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…
ORD > Cincinnati, Ohio: Biz from $436 Econ from $153. – Jun-Aug (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 > San Salvador, El Salvador: Biz from $723 Econ from $272. – Jun-Aug (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 > Raleigh, North Carolina: Biz from $430 Econ from $80. – Jun-Aug (Including Summer Break) [SOLD OUT]
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Chattanooga, Tennessee: Biz from $406 Econ from $148. – Jun-Aug (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 > Lincoln, Nebraska: Econ from $148. – Jun-Aug (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…
MDW > Dallas, Texas: Biz from $557 Econ from $88. – Jun-Aug (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 > Philadelphia, Pennsylvania: Econ from $98. – Jun-Aug (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…
ORD > New York, New York: Biz from $427 Econ from $162. – Jun-Aug (Including Summer Break) [SOLD OUT]
Have you ever booked a cruise only to find out that the flight to get there was going to be…
ORD > Fort Lauderdale, Florida: Econ from $99. – 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…