Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Charleston, South Carolina: Biz from $332 Econ from $100.- 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 > Charlotte, North Carolina: Biz from $260 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 > New Orleans, Louisiana: Biz from $231 Econ from $78.- Jan-Mar
Have you ever booked a cruise only to find out that the flight to get there was going to be…
ORD > Newark, New Jersey: Biz from $188 Econ from $72.- Jan-Mar
Be sure to check out the “cruises” link below to see if you could take advantage of this cheap flight,…
ORD > Cuenca, Ecuador: Biz from $1027 Econ from $430.- Feb-Apr (Including Spring Break)
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > San Pedro Sula, Honduras: Biz from $490 Econ from $214.- 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 > San Salvador, El Salvador: Biz from $402 Econ from $180.- 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 $278 Econ from $64. – 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 > Cozumel, Mexico: Biz from $1125 Econ from $332. – Feb-Apr (Including Spring 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 $323 Econ from $133.- Dec-Feb (Including MLK Weekend) [SOLD OUT]
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
ORD > Kingston, Jamaica: Biz from $650 Econ from $337.- 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 > New York, New York: Biz from $388 Econ from $57.- Dec-Feb (Including MLK Weekend) [SOLD OUT]
Have you ever booked a cruise only to find out that the flight to get there was going to be…
ORD > Cartagena, Colombia: Biz from $574 Econ from $229.- 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 > Austin, Texas: Biz from $311 Econ from $73.- Dec-Feb [SOLD OUT]
JGOOT Subscriber tells us about his $97 round-trip direct flight to Austin (that he has paid $350 for in the…
ORD > Fort Myers, Florida: Biz from $265 Econ from $59.- Jan-Mar
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Guatemala City, Guatemala: Biz from $685 Econ from $207.- Apr-Jun
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Palanga, Lithuania: Biz from $2242 Econ from $436.- Jan-Mar [SOLD OUT]
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Oranjestad, Aruba: Biz from $475 Econ from $229.- Dec-Feb [SOLD OUT]
When we went to Aruba – we stayed at the Renaissance, and it was fantastic. They have their own private…
ORD > Bogota, Colombia: Biz from $601 Econ from $264.- Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Gdansk, Poland: Biz from $1767 Econ from $424.- Jan-Mar [SOLD OUT]
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Louisville, Kentucky: Biz from $329 Econ from $166.- Dec-Feb (Including MLK Weekend) [SOLD OUT]
Bourbon Anyone? Click here to read a blog post from our Director of Support – Brooke Merkle – about her…
ORD > Belize City, Belize: Biz from $521 Econ from $281.- Jan-Mar
* There only appear to be a few seats at this price and availability is spotty. It will take a…
ORD > Cincinnati, Ohio: Biz from $383 Econ from $135.- Dec-Feb [SOLD OUT]
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Montego Bay, Jamaica: Biz from $513 Econ from $276.- Jan-Mar
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 $288 Econ from $61.- 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 > Baltimore, Maryland: Biz from $285 Econ from $57.- 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 > Cancun, Mexico: Biz from $386 Econ from $198.- Jan-Mar [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Boston, Massachusetts: Biz from $289 Econ from $127.- Dec-Feb [SOLD OUT]
I rarely post trips to Boston because they are typically so expensive and I advise using points instead of paying…
MDW > Dallas, Texas: Biz from $487 Econ from $62.- Jan-Mar
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > George Town, Cayman Islands: Biz from $524 Econ from $248.- 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 > Houston, Texas: Biz from $261 Econ from $72.- 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 > Managua, Nicaragua: Biz from $436 Econ from $211.- Dec-Feb (Including MLK Weekend) [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Atlanta, Georgia: Biz from $567 Econ from $48.- Jan-Mar [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 $460 Econ from $229.- 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 > Charlotte, North Carolina: Biz from $351 Econ from $94.- Jan-Mar
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > San Salvador, El Salvador: Biz from $446 Econ from $216.- Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Jacksonville, Florida: Biz from $509. Econ from $162. – 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 > New Orleans, Louisiana: Biz from $231. Econ from $75. – 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 > Coxen Hole, Honduras: Biz from $952. Econ from $472. – Dec-Feb (Including MLK Weekend) [SOLD OUT]
A lot of people are concerned about travel to Honduras, but Coxen Hole (AKA “Roatan”) is an island off of…