Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Louisville, Kentucky: Biz from $267 Econ from $97.- Nov-Jan
Bourbon Anyone? Click here to read a blog post from our Director of Support – Brooke Merkle – about her…
ORD > Lisbon, Portugal: Econ from $369.- Feb-Apr (Including Spring Break)
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Cancun, Mexico: Biz from $510 Econ from $200.- Dec-Feb
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Sao Paulo, Brazil: Biz from $1920 Econ from $432.- 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 > Philadelphia, Pennsylvania: Biz from $263 Econ from $61.- Dec-Feb (Including MLK Weekend)
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Baltimore, Maryland: Biz from $297 Econ from $58. – 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 > 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 > Bucharest, Romania: Econ from $517.- Dec-Feb
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Belgrade, Serbia: Econ from $512.- Apr-Jun
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
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 > Poznan, Poland: Econ from $375.- Feb-Apr (Including Spring Break)
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
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 > Krakow, Poland: Econ from $378.- 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 > 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 > Palanga, Lithuania: Econ from $401.- Dec-Feb
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
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 > Athens, Greece: Econ from $448.- Jan-Mar
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Marrakesh, Morocco: Econ from $508.- 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 > 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 > Osaka, Japan: Econ from $760. – Dec-Feb (Including MLK Weekend)
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
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 > Corfu, Greece: Econ from $692. – Feb-Apr (Including Spring Break)
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
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 > Malaga, Spain: Econ from $390. – Jan-Mar
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Auckland, New Zealand: Econ from $810. – Feb-Apr
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
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 > Phoenix, Arizona: Econ from $73. – Jan-Mar (Presidents day Weekend)
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 > Entebbe, Uganda: Econ from $870.- Mar-May
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
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 > Prague, Czech Republic: Econ from $410.- Dec-Feb
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Phuket City, Thailand: Econ from $624.- Jan-Mar (Presidents day Weekend)
* There only appear to be a few seats at this price and availability is spotty. It will take a…