For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Palanga, Lithuania: Econ from $507. – Dec-Feb (Including Winter Break)
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Cozumel, Mexico: Biz from $1109 Econ from $318. – Dec-Feb (Including Winter Break)
Cozumel is a completely separate part of mexico, and if you’ve ever thought about scuba diving, there isn’t a more…
MDW > Philadelphia, Pennsylvania: Econ from $80. – Nov-Jan (Including Winter Break) [SOLD OUT]
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
MDW > Atlanta, Georgia: Econ from $74. – Nov-Jan (Including Winter Break) [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 > Palanga, Lithuania: Econ from $557. – Dec-Feb (Including Winter Break) [SOLD OUT]
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Cluj Napoca, Romania: Econ from $464. – Dec-Feb (Including Winter Break) [SOLD OUT]
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 $510. – Nov-Jan (Including Winter Break) [SOLD OUT]
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
MDW > Toronto, Canada: Econ from $238. – Nov-Jan (Including Winter Break) [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Burbank, California: Econ from $81. – Dec-Feb (Including Winter Break) [SOLD OUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Burlington, Kentucky: Econ from $116. – 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 > Decatur, Georgia: Econ from $115. – Nov-Jan (Including Winter Break) [SOLD OUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Denver, Colorado: Biz from $425 Econ from $108. – Dec-Feb (Including Winter Break) [SOLD OUT]
If you visit Denver, be sure to drop me a note. I moved here from California 25 years ago, and…
ORD > Burlington, Kentucky: Econ from $119. – Dec-Feb (Including Winter Break) [SOLD OUT]
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
MDW > Kansas City, Kansas: Biz from $445 Econ from $145. – Dec-Feb (Including Winter Break) [SOLD OUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Sacramento, California: Econ from $127. – 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 > Peoria, Arizona: Biz from $289 Econ from $89. – 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 > Moscow, Russia: Biz from $1,822 Econ from $554. – Dec-Feb (Including Winter Break) [SOLD OUT]
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Memphis, Tennessee: Biz from $337 Econ from $117. – Dec-Feb (Including Winter Break) [SOLD OUT]
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Philadelphia, Pennsylvania: Econ from $63. – Dec-Feb (Including Winter Break) [SOLD OUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Marrakesh, Morocco: Econ from $567. – Dec-Feb (Including Winter Break) [SOLD OUT]
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Riga, Latvia: Biz from $1,934 Econ from $460. – Dec-Feb (Including Winter Break) [SOLD OUT]
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Stockholm, Sweden: Econ from $350. – Nov-Jan (Including Winter Break) [SOLD OUT]
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Decatur, Georgia: Econ from $115. – Nov-Jan (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 > Lviv, Ukraine: Biz from $1714 Econ from $432. – Jan-Mar (Including Winter Break) [SOLD OUT]
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Decatur, Georgia: Econ from $115. – Nov-Jan (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 > Burlington, Kentucky: Econ from $72. – 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 > Denver, Colorado: Biz from $355 Econ from $34. – Dec-Feb (Including Winter Break) [SOLD OUT]
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
ORD > Orlando, Florida: Econ from $31. – Nov-Jan (Including Winter Break) [SOLD OUT]
JGOOT Subscriber tells us about his wife & his flight to Orlando that was cheaper than driving. * This is…
ORD > Guayaquil, Ecuador: Biz from $1,059 Econ from $171. – Dec-Feb (Including Winter Break) [SOLD OUT]
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > San Diego, California: Biz from $432 Econ from $59. – Dec-Feb (Including Winter Break) [SOLD OUT]
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
ORD > Cancun, Mexico: Biz from $491 Econ from $141. – 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 > Oranjestad, Aruba: Biz from $888 Econ from $229. – Dec-Feb (Including Winter Break) [SOLD OUT]
When we went to Aruba – we stayed at the Renaissance, and it was fantastic. They have their own private…
ORD > Honolulu, Hawaii: Econ from $380. – Nov-Jan (Including Winter Break) [SOLD OUT]
* This is a “fare dump” with a few alternate dates available.
ORD > Phoenix, Arizona: Econ from $60. Biz from $487 (Business Bargain). – Nov-Jan (Including Winter Break) [SOLD OUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Decatur, Georgia: Econ from $98. – Nov-Jan (Including Winter Break) [SOLD OUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
MDW > Punta Gorda, Florida: Econ from $58. – Nov-Jan (Including Winter Break)
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
ORD > Las Vegas, Nevada: Econ from $53. – Nov-Jan (Including Winter Break)
Vegas Baby! * There only appear to be a few seats at this price and availability is spotty. It will…
ORD > Algiers, Algeria: Econ from $593. Biz from $2,430 (Business Bargain). – Nov-Jan (Including Winter Break)
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Riga, Latvia: Econ from $479. Biz from $1,679 (Business Bargain). – Nov-Jan (Including Winter Break) [SOLD OUT]
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…