Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Philadelphia, Pennsylvania: Econ from $70. Biz from $349 (Business Bargain). – Nov-Jan
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
ORD > San Salvador, El Salvador: Econ from $172. Biz from $458 (Business Bargain). – Nov-Jan
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Panama City, Panama: Econ from $187. Biz from $935 (Business Bargain). – Nov-Jan
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Orlando, Florida: Econ from $51. – Nov-Jan
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
ORD > Santo Domingo, Dominican Republic: Econ from $229. Biz from $540 (Business Bargain). – Nov-Jan
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Lihue, Hawaii: Econ from $303. – Nov-Jan
Lihue is the main city of Kauai. I’ve been to Hawaii three times, and Kauai is my favorite by far.…
ORD > Punta Cana, Dominican Republic: Econ from $219. Biz from $688 (Business Bargain). – Nov-Jan
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > New York, New York: Econ from $58. Biz from $275 (Business Bargain). – Nov-Jan
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: Econ from $165. Biz from $635 (Business Bargain). – Nov-Jan
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Baltimore, Maryland: Econ from $51. Biz from $345 (Business Bargain). – Nov-Jan
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 $256. Biz from $841 (Business Bargain). – Nov-Jan [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Anchorage, Alaska: Econ from $355. Biz from $722 (Business Bargain). – Nov-Jan [SOLD OUT]
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Oranjestad, Aruba: Econ from $236. Biz from $1,114 (Business Bargain). – Nov-Jan [SOLD OUT]
Our trip to Aruba was the beginning of JGOOT. I stumbled across ridiculously cheap flights, bundled that with quite a…
MDW > Thunder Bay, Canada: Econ from $211. – Nov-Jan [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Panama City, Panama: Econ from $257. Biz from $935 (Business Bargain). – Nov-Jan [SOLD OUT]
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
MDW > Lima, Peru: Econ from $387. – Nov-Jan [SOLD OUT]
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
MDW > Cancun, Mexico: Econ from $291. Biz from $673 (Business Bargain). – Nov-Jan [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Cusco, Peru: Econ from $383. Biz from $735 (Business Bargain). – Oct-Dec [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 > San Pedro Sula, Honduras: Econ from $256. Biz from $682 (Business Bargain). – Nov-Jan [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Austin, Texas: Econ from $26. Biz from $475 (Business Bargain). – Nov-Jan [SOLD OUT]
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
ORD > New York, New York: Econ from $73. Biz from $295 (Business Bargain). – Nov-Jan [SOLD OUT]
Have you ever booked a cruise only to find out that the flight to get there was going to be…
ORD > Phoenix, Arizona: Econ from $74. – Nov-Jan [SOLD OUT]
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
MDW > Toronto, Canada: Econ from $229. Biz from $551 (Business Bargain). – Nov-Jan [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Baltimore, Maryland: Econ from $50. Biz from $345 (Business Bargain). – Nov-Jan [SOLD OUT]
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 $479. Biz from $1,679 (Business Bargain). – Nov-Jan (Including Winter Break) [SOLD OUT]
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Minneapolis, Minnesota: Econ from $61. Biz from $259 (Business Bargain). – Nov-Jan [SOLD OUT]
JGOOT Subscriber tells us about his $63 round-trip direct flight to Minneapolis (among other adventures). * This is an airline…
ORD > Malaga, Spain: Econ from $372. – Nov-Jan [SOLD OUT]
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Bogota, Colombia: Econ from $220. Biz from $565 (Business Bargain). – Nov-Jan [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Fort Myers, Florida: Econ from $56. – Nov-Jan [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Panama City, Panama: Econ from $289. Biz from $974 (Business Bargain). – Nov-Jan [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Lima, Peru: Econ from $237. Biz from $472 (Business Bargain). – Nov-Jan [SOLD OUT]
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Philadelphia, Pennsylvania: Econ from $57. Biz from $349 (Business Bargain). – Nov-Jan [SOLD OUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Santiago, Chile: From $457 round-trip – Nov-Jan “Biz from $863” [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 > Copenhagen, Denmark: From $268 round-trip – Nov-Jan [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Mayaguez, Puerto Rico: From $288 round-trip – Nov-Jan *BB [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Dublin, Ireland: From $371 round-trip – Nov-Jan *BB [SOLD OUT]
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Odessa, Ukraine: From $401 round-trip – Nov-Jan [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 > Hamburg, Germany: From $358 round-trip – Nov-Jan [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
MDW > Knoxville, Tennessee: From $72 round-trip – Nov-Jan *BB [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…