Bourbon Anyone? Click here to read a blog post from our Director of Support – Brooke Merkle – about her…
ORD > Asheville, North Carolina: Econ from $166.- Dec-Feb
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > New Delhi, India: Econ from $661.- Jan-Mar
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Cincinnati, Ohio: Biz from $383 Econ from $135.- Dec-Feb
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > San Diego, California: Econ from $151.- Dec-Feb (Including MLK Weekend)
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Philadelphia, Pennsylvania: Biz from $288 Econ from $61.- Dec-Feb
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Baltimore, Maryland: Biz from $285 Econ from $57.- Dec-Feb
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
MDW > Bucharest, Romania: Econ from $577.- Jan-Mar
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Riga, Latvia: Econ from $460.- Jan-Mar
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Cancun, Mexico: Biz from $386 Econ from $198.- Jan-Mar
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Boston, Massachusetts: Biz from $289 Econ from $127.- Dec-Feb
I rarely post trips to Boston because they are typically so expensive and I advise using points instead of paying…
ORD > Malaga, Spain: Econ from $376.- Jan-Mar
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > George Town, Cayman Islands: Biz from $524 Econ from $248.- Dec-Feb
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Orlando, Florida: Econ from $58.- Dec-Feb (Including MLK Weekend)
JGOOT Subscriber tells us about his wife & his flight to Orlando that was cheaper than driving. * This is…
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.…
MDW > Atlanta, Georgia: Biz from $567 Econ from $48.- Jan-Mar
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Algiers, Algeria: Econ from $549.- Jan-Mar
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 $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.…
MDW > Newark, New Jersey: Econ from $53. – Dec-Feb (Including MLK Weekend)
Have you ever booked a cruise only to find out that the flight to get there was going to be…
MDW > Tunis, Tunisia: Econ from $849. – Jan-Mar
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Jacksonville, Florida: Biz from $509. Econ from $162. – 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 > Hong Kong, Hong Kong: Econ from $710. – Jan-Mar
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
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 > Dublin, Ireland: Econ from $346. – Jan-Mar
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 $589. – 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 > Cluj Napoca, Romania: Econ from $497. – Jan-Mar
On a tight budget? Consider Eastern Europe over Western Europe. You’ll stretch your travel budget two or three times as…
ORD > Cartagena, Colombia: Biz from $625 Econ from $247. – Dec-Feb
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Wroclaw, Poland: Econ from $385. – Dec-Feb (Including MLK Weekend)
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > New York, New York: Biz from $402 Econ from $58. – Dec-Feb
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 $930 Econ from $355. – Dec-Feb
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Minneapolis, Minnesota: Biz from $376 Econ from $88. – Dec-Feb (Including Winter Break)
JGOOT Subscriber tells us about his $63 round-trip direct flight to Minneapolis (among other adventures). * This is a “fare…
ORD > Austin, Texas: Biz from $290 Econ from $80. – Dec-Feb (Including MLK Weekend)
JGOOT Subscriber tells us about his $97 round-trip direct flight to Austin (that he has paid $350 for in the…
ORD > Nadi, Fiji: Econ from $1074. – Dec-Feb (Including MLK 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 $281 Econ from $71.- Dec-Feb
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Kralendijk, Caribbean Netherlands: Biz from $1284 Econ from $519. – Dec-Feb
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Portland, Oregon: Econ from $180. – Dec-Feb
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Las Vegas, Nevada: Econ from $87. – Dec-Feb
Grab this flight and spend the savings on several shows. (I highly recommend the Michael Jackson show, as well as…
ORD > Leon, Mexico: Biz from $652. Econ from $264. – Dec-Feb
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Kansas City, Kansas: Biz from $421. Econ from $153. – Dec-Feb
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Reno, Nevada: Econ from $161. – Dec-Feb (Including Winter Break)
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…