Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Seattle, Washington: Biz from $538 Econ from $149. – Jul-Sep
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Piarco, Trinidad and Tobago: Biz from $925 Econ from $452. – Jan-Mar (Including President’s Day Weekend)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Belgrade, Serbia: Biz from $1848 Econ from $605. – Oct-Dec
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
MDW > Raleigh, North Carolina: Biz from $439 Econ from $99. – May-Jul (Including Summer Break)
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
ORD > Guadalajara, Mexico: Biz from $760 Econ from $248. – Aug-Oct
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Dallas, Texas: Biz from $545 Econ from $52. – May-Jul (Including Summer Break)
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
MDW > Tunis, Tunisia: Biz from $2835 Econ from $897. – Feb-Apr
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > San Salvador, El Salvador: Biz from $812 Econ from $227. – 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 > Kingston, Jamaica: Biz from $800 Econ from $490. – Oct-Dec (Including Thanksgiving)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Monterrey, Mexico: Biz from $686 Econ from $231. – 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 > Philadelphia, Pennsylvania: Biz from $409 Econ from $67. – May-Jul (Including Summer Break)
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
ORD > Abuja, Nigeria: Biz from $3510 Econ from $972. – Sep-Nov
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Cali, Colombia: Biz from $890 Econ from $251. – 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 > Kansas City, Kansas: Biz from $297 Econ from $141. – 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…
ORD > Charlotte, North Carolina: Biz from $397 Econ from $51. – May-Jul (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 > Barranquilla, Colombia: Biz from $834 Econ from $328. – Aug-Oct
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Toronto, Canada: Biz from $676 Econ from $267. – May-Jul (Including Summer Break)
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Minneapolis, Minnesota: Biz from $287 Econ from $84. – Jun-Aug (Including Summer Break)
JGOOT Subscriber tells us about his $63 round-trip direct flight to Minneapolis (among other adventures). * This is a “fare…
MDW > Denver, Colorado: Biz from $502 Econ from $58. – Aug-Oct
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
ORD > Cozumel, Mexico: Biz from $715 Econ from $315. – Sep-Nov (Including Fall Break)
Cozumel is a completely separate part of mexico, and if you’ve ever thought about scuba diving, there isn’t a more…
ORD > Nashville, Tennessee: Biz from $417 Econ from $67. – May-Jul (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 > Atlanta, Georgia: Biz from $506 Econ from $47. – 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 > Santo Domingo, Dominican Republic: Biz from $836 Econ from $259. – 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 > 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 > Pula, Croatia: Biz from $2298 Econ from $589. – Aug-Oct
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
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 > 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.…
ORD > Belgrade, Serbia: Biz from $2210 Econ from $607. – Sep-Nov (Including Fall Break)
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
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 > 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.…
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.…