Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Cartagena, Colombia: Biz from $625 Econ from $247. – Dec-Feb [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Denver, Colorado: Biz from $345 Econ from $93. – Feb-Apr
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: Biz from $402 Econ from $58. – Dec-Feb [SOLD OUT]
Be sure to check out the “cruises” link below to see if you could take advantage of this cheap flight,…
ORD > Kingston, Jamaica: Biz from $930 Econ from $355. – Dec-Feb [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Minneapolis, Minnesota: Biz from $376 Econ from $88. – Dec-Feb (Including Winter Break) [SOLD OUT]
JGOOT Subscriber tells us about his $63 round-trip direct flight to Minneapolis (among other adventures). * This is a “fare…
ORD > Austin, Texas: Biz from $290 Econ from $80. – Dec-Feb (Including MLK Weekend) [SOLD OUT]
JGOOT Subscriber tells us about his $97 round-trip direct flight to Austin (that he has paid $350 for in the…
ORD > Cozumel, Mexico: Biz from $1025 Econ from $332. – Aug-Oct
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 $281 Econ from $71.- Dec-Feb [SOLD OUT]
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Oranjestad, Aruba: Biz from $486 Econ from $238.- Dec-Feb [SOLD OUT]
Our trip to Aruba was the beginning of JGOOT. I stumbled across ridiculously cheap flights, bundled that with quite a…
ORD > Kralendijk, Caribbean Netherlands: Biz from $1284 Econ from $519. – Dec-Feb [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Leon, Mexico: Biz from $652. Econ from $264. – Dec-Feb [SOLD OUT]
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: Biz from $367. Econ from $135. – Nov-Jan (Including Winter Break) [SOLD OUT]
Have you ever booked a cruise only to find out that the flight to get there was going to be…
ORD > Kansas City, Kansas: Biz from $421. Econ from $153. – Dec-Feb [SOLD OUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Nassau, The Bahamas: Biz from $810. Econ from $240. – Jan-Mar
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 $401. Econ from $137. – Dec-Feb (Including MLK Weekend) [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Louisville, Kentucky: Biz from $267 Econ from $97.- Nov-Jan [SOLD OUT]
Bourbon Anyone? Click here to read a blog post from our Director of Support – Brooke Merkle – about her…
ORD > Cancun, Mexico: Biz from $510 Econ from $200.- Dec-Feb [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Sao Paulo, Brazil: Biz from $1920 Econ from $432.- Feb-Apr (Including Spring Break)
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Philadelphia, Pennsylvania: Biz from $263 Econ from $61.- Dec-Feb (Including MLK Weekend) [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Baltimore, Maryland: Biz from $297 Econ from $58. – Dec-Feb (Including MLK Weekend) [SOLD OUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Liberia, Costa Rica: Biz from $976 Econ from $345.- Dec-Feb (Including MLK Weekend) [SOLD OUT]
When I went to Costa Rica, I flew into Liberia. Nothing special there, but you’re only about a half-hour from…
ORD > Boston, Massachusetts: Biz from $334 Econ from $117.- Dec-Feb [SOLD OUT]
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Fort Myers, Florida: Biz from $265 Econ from $59.- Dec-Feb [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Montego Bay, Jamaica: Biz from $537 Econ from $289.- Dec-Feb [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Riga, Latvia: Biz from $1991 Econ from $426.- Dec-Feb [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 > Orlando, Florida: Biz from $325 Econ from $58.- Jan-Mar [SOLD OUT]
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
ORD > Dallas, Texas: Biz from $311 Econ from $57.- Dec-Feb (Including Winter Break) [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Managua, Nicaragua: Biz from $505 Econ from $261.- Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Houston, Texas: Biz from $487 Econ from $57.- Dec-Feb [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 > Atlanta, Georgia: Biz from $567 Econ from $58.- Dec-Feb [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > San Pedro Sula, Honduras: Biz from $588 Econ from $246.- Jan-Mar [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Norfolk, Virginia: Biz from $463. Econ from $115. – 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 > Hartford, Connecticut: Biz from $427. Econ from $157. – Dec-Feb [SOLD OUT]
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
ORD > Charlotte, North Carolina: Biz from $237. Econ from $57. – Jan-Mar
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Belize City, Belize: Biz from $640. Econ from $303. – Dec-Feb [SOLD OUT]
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
ORD > Charleston, South Carolina: Biz from $378 Econ from $134.- Jan-Mar
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
ORD > George Town, Cayman Islands: Biz from $555 Econ from $293.- Dec-Feb [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 Lauderdale, Florida: Biz from $237 Econ from $61.- 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 > Dublin, Ireland: Biz from $1056 Econ from $346.- Dec-Feb [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…