Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Malaga, Spain: Econ from $390. – Jan-Mar [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
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 > 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 > Prague, Czech Republic: Econ from $410.- Dec-Feb [SOLD OUT]
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…
ORD > Gdansk, Poland: Econ from $389.- Jan-Mar [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Ontario, California: Econ from $142.- Nov-Jan [SOLD OUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Dublin, Ireland: Biz from $1056 Econ from $346.- Dec-Feb [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Cartagena, Colombia: Biz from $596 Econ from $251.- Dec-Feb [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Cluj Napoca, Romania: Econ from $515.- Mar-May (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 > Dubai, United Arab Emirates: Econ from $589.- 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 > Larnaca, Cyprus: Econ from $493.- 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 > Budapest, Hungary: Econ from $421.- Feb-Apr
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Minneapolis, Minnesota: Biz from $343. Econ from $62. – Nov-Jan [SOLD OUT]
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Male, Maldives: Econ from $885. – 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 > Bucharest, Romania: Econ from $523. – 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 > Wroclaw, Poland: Econ from $491. – Jan-Mar
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Portland, Oregon: Econ from $142. – Nov-Jan [SOLD OUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Kralendijk, Caribbean Netherlands: Biz from $1508. Econ from $451. – Feb-Apr [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Nadi, Fiji: Econ from $887. – 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 > Luqa, Malta: Econ from $492. – Jan-Mar [SOLD OUT]
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Boston, Massachusetts: Biz from $343 Econ from $110.- Dec-Feb (Including MLK Weekend) [SOLD OUT]
I rarely post trips to Boston because they are typically so expensive and I advise using points instead of paying…
ORD > Montego Bay, Jamaica: Biz from $566 Econ from $299.- 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 > Poznan, Poland: Econ from $385.- 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…
MDW > Orlando, Florida: Econ from $57.- Dec-Feb [SOLD OUT]
JGOOT Subscriber tells us about his wife & his flight to Orlando that was cheaper than driving. * There only…
ORD > Barcelona, Spain: Econ from $355.- Mar-May
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Marrakesh, Morocco: Econ from $509.- 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 > Managua, Nicaragua: Biz from $520 Econ from $214.- Nov-Jan [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Houston, Texas: Biz from $286 Econ from $57.- 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 > Atlanta, Georgia: Biz from $249 Econ from $57.- 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 > Riga, Latvia: Econ from $534.- 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 > Krakow, Poland: Econ from $388. – Jan-Mar (Presidents day Weekend)
Want to stretch your vacation dollars two to three times farther? Consider Eastern Europe over Western Europe. You’ll stretch your…
MDW > Casablanca, Morocco: Econ from $780. – Feb-Apr
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
MDW > San Diego, California: Econ from $155. – Nov-Jan (Including Thanksgiving) [SOLD OUT]
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Prague, Czech Republic: Econ from $447. – 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 > Reno, Nevada: Econ from $130. – Nov-Jan [SOLD OUT] [SOLD OUT]
Whether boating in the summer, skiing in the winter, hiking to take in the beautiful scenery, or gambling at the…
ORD > Bangkok, Thailand: Econ from $682. – Jan-Mar [SOLD OUT]
* This is a “fare dump” with a few alternate dates available.
ORD > Coxen Hole, Honduras: Biz from $1424. Econ from $489. – Nov-Jan
A lot of people are concerned about travel to Honduras, but Coxen Hole (AKA “Roatan”) is an island off of…