Our trip to Aruba was the beginning of JGOOT. I stumbled across ridiculously cheap flights, bundled that with quite a…
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 > 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.…
MDW > San Diego, California: Econ from $109. – Apr-Jun
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
MDW > San Francisco, California: Econ from $104. – Apr-Jun
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
MDW > Orlando, Florida: Econ from $51. – Apr-Jun
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
ORD > Medellin, Colombia: Biz from $814 Econ from $237. – Apr-Jun
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Miami, Florida: Econ from $56. – Apr-Jun
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Houston, Texas: Econ from $68. – Apr-Jun
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Cancun, Mexico: Biz from $703 Econ from $183. – Apr-Jun
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Seattle, Washington: Biz from $588 Econ from $139. – 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: Biz from $444 Econ from $58. – Apr-Jun
3 different flights to/from Raleigh – All under $100 round-trip. * This is a “fare dump” with a few alternate…
ORD > Guadalajara, Mexico: Biz from $803 Econ from $273. – 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 $429 Econ from $100. – Apr-Jun
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Los Angeles, California: Econ from $85. – Apr-Jun
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Bogota, Colombia: Biz from $729 Econ from $240. – Apr-Jun
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Washington, DC: Econ from $51. – Apr-Jun
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Atlantic City, New Jersey: Biz from $__ Econ from $93. – Apr-Jun
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
MDW > San Juan, Puerto Rico: Econ from $133. – Apr-Jun
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Myrtle Beach, South Carolina: Econ from $103. – Apr-Jun
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > New Orleans, Louisiana: Econ from $63. – 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 > 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,…