* There only appear to be a few seats at this price and availability is spotty. It will take a…

ORD > Managua, Nicaragua: Biz from $436 Econ from $211.- Dec-Feb (Including MLK Weekend)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

ORD > San Pedro Sula, Honduras: Biz from $460 Econ from $229.- Dec-Feb
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 $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 > Coxen Hole, Honduras: Biz from $952. Econ from $472. – Dec-Feb (Including MLK Weekend)
A lot of people are concerned about travel to Honduras, but Coxen Hole (AKA “Roatan”) is an island off of…

ORD > Liberia, Costa Rica: Biz from $976 Econ from $345.- Dec-Feb (Including MLK Weekend)
When I went to Costa Rica, I flew into Liberia. Nothing special there, but you’re only about a half-hour from…

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 > 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.…

MDW > San Salvador, El Salvador: Econ from $286. – Dec-Feb (Including MLK Weekend)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

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 > 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 > 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 > Coxen Hole, Honduras: Biz from $1424. Econ from $489. – Nov-Jan
A lot of people are concerned about travel to Honduras, but Coxen Hole (AKA “Roatan”) is an island off of…

ORD > San Pedro Sula, Honduras: Biz from $503 Econ from $237. – Nov-Jan
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

ORD > Guatemala City, Guatemala: Biz from $436. Econ from $218. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

MDW > Saint Thomas Island, U.S. Virgin Islands: Econ from $275. – Dec-Feb
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

ORD > Managua, Nicaragua: Biz from $639 Econ from $262.- Nov-Jan
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

ORD > San Pedro Sula, Honduras: Biz from $489 Econ from $243.- Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

ORD > Belize City, Belize: Econ from $363. – Dec-Feb (Including Winter Break)
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…

ORD > Managua, Nicaragua: Biz from $774 Econ from $234. – Oct-Dec
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

ORD > Liberia, Costa Rica: Biz from $952. Econ from $307. – Dec-Feb
When I went to Costa Rica, I flew into Liberia. Nothing special there, but you’re only about a half-hour from…

ORD > Belize City, Belize: Biz from $696. Econ from $376. – Nov-Jan
* This is a “fare dump” with a few alternate dates available.

MDW > San Jose, Costa Rica: Biz from $702 Econ from $326. – Oct-Dec
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

MDW > San Pedro Sula, Honduras: Biz from $1259. Econ from $267. – Oct-Dec
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 $759. Econ from $214. – Oct-Dec
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

ORD > Liberia, Costa Rica: Biz from $1257 Econ from $309. – Sep-Nov (Including Fall Break) [SOLD OUT]
When I went to Costa Rica, I flew into Liberia. Nothing special there, but you’re only about a half-hour from…

MDW > San Jose, Costa Rica: Econ from $344. – 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 > Managua, Nicaragua: Biz from $1012 Econ from $234. – Apr-Jun
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

ORD > Guatemala City, Guatemala: Biz from $508 Econ from $196.- Sep-Nov [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

ORD > Liberia, Costa Rica: Biz from $1190 Econ from $369. – Nov-Jan
When I went to Costa Rica, I flew into Liberia. Nothing special there, but you’re only about a half-hour from…
