Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
MDW > Asheville, North Carolina: Econ from $97. – May-Jul (Including Summer Break)
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 $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 > 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 > Brasilia, Brazil: Biz from $2314 Econ from $636.- Jan-Mar (Presidents day Weekend)
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Fort Myers, Florida: Biz from $266 Econ from $61.- 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…
MDW > Asheville, North Carolina: Econ from $116. – May-Jul (Including Summer Break)
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
ORD > Orlando, Florida: Biz from $373 Econ from $68.- Jan-Mar (Presidents day Weekend)
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
ORD > Tokyo, Japan: Econ from $697.- Jan-Mar (Presidents day Weekend)
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Cuenca, Ecuador: Biz from $1007 Econ from $411.- Jan-Mar (Presidents day Weekend)
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 $436.- Jan-Mar (Presidents day Weekend)
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Montego Bay, Jamaica: Biz from $531 Econ from $278.- Jan-Mar (Presidents day Weekend)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Dubai, United Arab Emirates: Econ from $730.- Jan-Mar (Presidents day Weekend)
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
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,…
MDW > Lisbon, Portugal: Econ from $501.- Jan-Mar (Presidents day Weekend)
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
MDW > Denver, Colorado: Econ from $86.- 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 > 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 > Madrid, Spain: Econ from $387.- Dec-Feb (Including MLK Weekend) [SOLD OUT]
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Colombo, Sri Lanka: Econ from $748.- 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 > Norfolk, Virginia: Econ from $130.- Dec-Feb (Including MLK Weekend) [SOLD OUT]
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
ORD > Las Vegas, Nevada: Econ from $110.- Apr-Jun (Including Summer Break)
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
ORD > Kochi, India: Econ from $679.- Feb-Apr (Including Spring Break)
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
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 > San Diego, California: Econ from $151.- Dec-Feb (Including MLK Weekend) [SOLD OUT]
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Cairo, Egypt: Econ from $642.- Feb-Apr (Including Spring Break)
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
MDW > Orlando, Florida: Econ from $58.- Dec-Feb (Including MLK Weekend) [SOLD OUT]
JGOOT Subscriber tells us about his wife & his flight to Orlando that was cheaper than driving. * This is…
ORD > Krakow, Poland: Econ from $390.- Jan-Mar (Presidents day Weekend)
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
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 > Newark, New Jersey: Econ from $53. – 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 > Male, Maldives: Econ from $919.- 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 > Innsbruck, Austria: Econ from $613.- Jan-Mar (Presidents day Weekend)
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > San Diego, California: Econ from $122.- 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 > 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 > 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) [SOLD OUT]
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) [SOLD OUT]
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) [SOLD OUT]
When I went to Costa Rica, I flew into Liberia. Nothing special there, but you’re only about a half-hour from…
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 > Dallas, Texas: Biz from $311 Econ from $57.- Dec-Feb (Including Winter Break) [SOLD OUT]
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…