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 > Gdansk, Poland: Econ from $439.- 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 > 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 > Malaga, Spain: Econ from $393. – Mar-May
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Palanga, Lithuania: Econ from $472. – 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 > Jakarta, Indonesia: Econ from $705. – Apr-Jun
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Bucharest, Romania: Econ from $496. – Apr-Jun
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
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 > Dublin, Ireland: Econ from $387. – Mar-May
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Dubai, United Arab Emirates: Econ from $566. – Mar-May
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Tokyo, Japan: Econ from $847. – Apr-Jun
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
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 > Krakow, Poland: Econ from $428.- Nov-Jan
Want to stretch your vacation dollars two to three times farther? Consider Eastern Europe over Western Europe. You’ll stretch your…
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 > Riga, Latvia: Econ from $424.- Mar-May
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > San Antonio, Texas: Econ from $144.- Feb-Apr
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Charleston, South Carolina: Econ from $119.- Feb-Apr
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
MDW > Tunis, Tunisia: Econ from $856.- Feb-Apr (Including Spring Break)
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Luqa, Malta: Econ from $523.- Feb-Apr
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
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 > Ontario, California: Econ from $182.- Mar-May
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
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 > Paphos, Cyprus: Econ from $614.- Apr-Jun
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
MDW > San Juan, Puerto Rico: Econ from $190.- Feb-Apr
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
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…
ORD > Newark, New Jersey: Biz from $213 Econ from $80.- Jan-Mar (Presidents day Weekend)
Be sure to check out the “cruises” link below to see if you could take advantage of this cheap flight,…
ORD > New Orleans, Louisiana: Biz from $210 Econ from $69.- 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 > Rzeszow, Poland: Econ from $451. – Feb-Apr
On a tight budget? Consider Eastern Europe over Western Europe. You’ll stretch your travel budget two or three times as…
ORD > Budapest, Hungary: Econ from $454.- Feb-Apr (Including Spring Break)
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > San Pedro Sula, Honduras: Biz from $720 Econ from $263.- Apr-Jun
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…