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ORD > Kralendijk, Caribbean Netherlands: Biz from $1168 Econ from $573. – Dec-Feb 

ORD > Kralendijk, Caribbean Netherlands: Biz from $1168 Econ from $573. – Dec-Feb 

Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

ORD > Innsbruck, Austria: Econ from $545. – Jan-Mar (Presidents day Weekend) 

ORD > Innsbruck, Austria: Econ from $545. – 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 > Tokyo, Japan: Econ from $680. – Oct-Dec 

ORD > Tokyo, Japan: Econ from $680. – Oct-Dec  [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 > Athens, Greece: Econ from $456. – Feb-Apr (Including Spring Break) 

ORD > Athens, Greece: Econ from $456. – 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 > Heraklion, Greece: Econ from $642. – Oct-Dec 

ORD > Heraklion, Greece: Econ from $642. – Oct-Dec 

Be sure to check the flight plus hotel price below! Sometimes, you can get your hotel for nearly free –…

ORD > Chennai, India: Econ from $751. – Oct-Dec 

ORD > Chennai, India: Econ from $751. – Oct-Dec  [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 > Bali, Indonesia: Econ from $687. – Oct-Dec 

ORD > Bali, Indonesia: Econ from $687. – Oct-Dec 

For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…

ORD > Dubai, United Arab Emirates: Econ from $553. – Oct-Dec (Including Thanksgiving) 

ORD > Dubai, United Arab Emirates: Econ from $553. – Oct-Dec (Including Thanksgiving) 

Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…

ORD > Kralendijk, Caribbean Netherlands: Biz from $1167 Econ from $573. – Dec-Feb 

ORD > Kralendijk, Caribbean Netherlands: Biz from $1167 Econ from $573. – Dec-Feb 

Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

ORD > George Town, Cayman Islands: Biz from $616 Econ from $311. – Nov-Jan

ORD > George Town, Cayman Islands: Biz from $616 Econ from $311. – Nov-Jan

Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

ORD > Algiers, Algeria: Econ from $580. – Nov-Jan (Including Thanksgiving) 

ORD > Algiers, Algeria: Econ from $580. – Nov-Jan (Including Thanksgiving) 

For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…

ORD > Abu Dhabi, United Arab Emirates: Econ from $569. – Sep-Nov (Including Fall Break)

ORD > Abu Dhabi, United Arab Emirates: Econ from $569. – Sep-Nov (Including Fall 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…

MDW > Tunis, Tunisia: Biz from $2627 Econ from $809. – Oct-Dec 

MDW > Tunis, Tunisia: Biz from $2627 Econ from $809. – Oct-Dec 

For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…

ORD > New Delhi, India: Econ from $661.- Oct-Dec

ORD > New Delhi, India: Econ from $661.- Oct-Dec

Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…

ORD > Colombo, Sri Lanka: Econ from $687.- Sep-Nov (Including Fall Break)

ORD > Colombo, Sri Lanka: Econ from $687.- Sep-Nov (Including Fall 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 > Chennai, India: Econ from $764.- Sep-Nov (Including Fall Break)

ORD > Chennai, India: Econ from $764.- Sep-Nov (Including Fall 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 > Kathmandu, Nepal: Econ from $744. – Feb-Apr 

ORD > Kathmandu, Nepal: Econ from $744. – Feb-Apr 

For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…

ORD > Dubrovnik, Croatia: Econ from $625. – Sep-Nov (Including Fall Break) 

ORD > Dubrovnik, Croatia: Econ from $625. – Sep-Nov (Including Fall Break)  [SOLD OUT]

* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…

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