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
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
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
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
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
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)
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
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
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
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
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
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
* 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
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
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
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Cartagena, Colombia: Biz from $596 Econ from $251.- Dec-Feb
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Kingston, Jamaica: Biz from $765 Econ from $330.- Dec-Feb
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > New Orleans, Louisiana: Biz from $427 Econ from $45.- 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 > New York, New York: Biz from $412 Econ from $73. – Dec-Feb (Including Winter Break)
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Denver, Colorado: Biz from $484 Econ from $49.- Nov-Jan
Looking for a more unique bar than one of dozens of national chains on 16th street? Here are several amazing…
ORD > Austin, Texas: Biz from $302 Econ from $65.- Jan-Mar
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 $1003 Econ from $246.- Feb-Apr
Cozumel is a completely separate part of mexico, and if you’ve ever thought about scuba diving, there isn’t a more…
ORD > Minneapolis, Minnesota: Biz from $343. Econ from $62. – Nov-Jan
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Liberia, Costa Rica: Biz from $1038. Econ from $371. – Feb-Apr (Including Spring Break)
When I went to Costa Rica, I flew into Liberia. Nothing special there, but you’re only about a half-hour from…
ORD > Baltimore, Maryland: Biz from $345. Econ from $58. – Nov-Jan
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Kralendijk, Caribbean Netherlands: Biz from $1508. Econ from $451. – Feb-Apr
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 $419 Econ from $138. – 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: Biz from $703 Econ from $225. – Mar-May
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Boston, Massachusetts: Biz from $343 Econ from $110.- Dec-Feb (Including MLK Weekend)
I rarely post trips to Boston because they are typically so expensive and I advise using points instead of paying…
ORD > Los Angeles, California: Biz from $290 Econ from $72.- Nov-Jan
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Montego Bay, Jamaica: Biz from $566 Econ from $299.- Nov-Jan (Including Winter Break)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Newark, New Jersey: Biz from $191 Econ from $84.- Jan-Mar
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 $520 Econ from $214.- Nov-Jan
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 $286 Econ from $57.- Dec-Feb (Including MLK Weekend)
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
ORD > Atlanta, Georgia: Biz from $249 Econ from $57.- Dec-Feb (Including MLK Weekend)
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Cancun, Mexico: Biz from $530 Econ from $202.- Dec-Feb
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…