Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Charlotte, North Carolina: Biz from $281 Econ from $94.- Feb-Apr (Including Spring Break)
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Fort Lauderdale, Florida: Biz from $295 Econ from $51.- Feb-Apr
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 $769 Econ from $387.- Mar-May
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Newark, New Jersey: Biz from $423 Econ from $56. – Feb-Apr
Be sure to check out the “cruises” link below to see if you could take advantage of this cheap flight,…
ORD > Cartagena, Colombia: Biz from $577 Econ from $237. – Feb-Apr (Including Spring Break)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Raleigh, North Carolina: Biz from $406 Econ from $110.- Feb-Apr
3 different flights to/from Raleigh – All under $100 round-trip. * There only appear to be a few seats at…
ORD > Guatemala City, Guatemala: Biz from $667 Econ from $233.- Apr-Jun
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 $352 Econ from $150. – Feb-Apr
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Willemstad, Curaçao: Biz from $1086 Econ from $377. – Feb-Apr (Including Spring Break)
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 $499 Econ from $87.- Feb-Apr
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Miami, Florida: Biz from $212 Econ from $50.- Feb-Apr (Including Spring Break)
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
ORD > Punta Cana, Dominican Republic: Biz from $682 Econ from $191.- Feb-Apr (Including Spring Break)
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 $458 Econ from $88.- Feb-Apr
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Oranjestad, Aruba: Biz from $531 Econ from $218.- Feb-Apr
If you visit Aruba, be sure to visit Flying Fishbone. Best dining experience Michelle and I have ever had. *…
ORD > Jacksonville, Florida: Biz from $517 Econ from $128.- Feb-Apr
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Los Angeles, California: Biz from $344 Econ from $88.- Feb-Apr (Including Spring Break)
Be sure to check out the “cruises” links below to see if you could grab this cheap flight, and hop…
ORD > Mexico City, Mexico: Biz from $680 Econ from $208.- Feb-Apr
Although I’ve been to about half a dozen cities in Mexico, Mexico City isn’t one of them. Several of my…
ORD > Fort Myers, Florida: Biz from $271 Econ from $52.- Feb-Apr
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > New York, New York: Biz from $170 Econ from $50.- Feb-Apr
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Cuenca, Ecuador: Biz from $1007 Econ from $440.- 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 Jose, Costa Rica: Biz from $557 Econ from $214.- Feb-Apr
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 $286 Econ from $104.- Feb-Apr (Including Spring Break)
I rarely post trips to Boston because they are typically so expensive and I advise using points instead of paying…
ORD > Baltimore, Maryland: Biz from $279 Econ from $73.- Feb-Apr
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 $556 Econ from $251.- Feb-Apr
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 $354 Econ from $112. – Jan-Mar (Presidents day Weekend)
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Seattle, Washington: Biz from $616 Econ from $177. – Jan-Mar (Presidents day Weekend)
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Houston, Texas: Biz from $303 Econ from $60. – 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 $582 Econ from $266. – Mar-May
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Dallas, Texas: Biz from $309 Econ from $83. – Apr-Jun
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Orlando, Florida: Biz from $238 Econ from $65. – Feb-Apr
JGOOT Subscriber tells us about his wife & his flight to Orlando that was cheaper than driving. * This is…
ORD > Liberia, Costa Rica: Biz from $1094 Econ from $392. – Mar-May
When I went to Costa Rica, I flew into Liberia. Nothing special there, but you’re only about a half-hour from…
ORD > Atlantic City, New Jersey: Biz from $651 Econ from $150. – Jan-Mar
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Georgetown, Guyana: Biz from $742 Econ from $401. – Feb-Apr
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Cancun, Mexico: Biz from $494 Econ from $239. – Feb-Apr (Including Spring Break)
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
MDW > Atlanta, Georgia: Biz from $557 Econ from $58.- Jan-Mar (Presidents day Weekend)
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > San Salvador, El Salvador: Biz from $499 Econ from $206.- Feb-Apr
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Guadalajara, Mexico: Biz from $736 Econ from $239.- Feb-Apr (Including Spring Break)
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 $304 Econ from $54.- Feb-Apr
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Guayaquil, Ecuador: Biz from $613 Econ from $265.- Apr-Jun
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…