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ORD > Melbourne, Australia: Econ from $1043. – Feb-Apr 

ORD > Melbourne, Australia: Econ from $1043. – 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 > Dhaka, Bangladesh: Econ from $783. – Mar-May 

ORD > Dhaka, Bangladesh: Econ from $783. – 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 > Sapporo, Japan: Econ from $873. – Dec-Feb

ORD > Sapporo, Japan: Econ from $873. – Dec-Feb

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

ORD > Auckland, New Zealand: Econ from $961. – Jan-Mar

ORD > Auckland, New Zealand: Econ from $961. – 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 > Abu Dhabi, United Arab Emirates: Econ from $764. – Feb-Apr

ORD > Abu Dhabi, United Arab Emirates: Econ from $764. – 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 > Almaty, Kazakhstan: Econ from $821.- Feb-Apr

ORD > Almaty, Kazakhstan: Econ from $821.- 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 > Cairns, Australia: Econ from $1088. – Nov-Jan

ORD > Cairns, Australia: Econ from $1088. – Nov-Jan

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

ORD > George Town, Cayman Islands: Biz from $463. Econ from $271. – Nov-Jan

ORD > George Town, Cayman Islands: Biz from $463. Econ from $271. – Nov-Jan

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

ORD > Male, Maldives: Econ from $950. – Jan-Mar (Presidents day Weekend) 

ORD > Male, Maldives: Econ from $950. – Jan-Mar (Presidents day Weekend) 

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

ORD > Auckland, New Zealand: Econ from $1019. – Oct-Dec 

ORD > Auckland, New Zealand: Econ from $1019. – Oct-Dec 

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

ORD > Phu Quoc, Vietnam: Econ from $992. – Feb-Apr (Including Spring Break) 

ORD > Phu Quoc, Vietnam: Econ from $992. – Feb-Apr (Including Spring Break) 

Do you like Vietnamese Pho? Here is a recipe my childhood friend Hien taught me. * This is an airline…

ORD > Okinawa, Japan: Econ from $961. – Oct-Dec

ORD > Okinawa, Japan: Econ from $961. – 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 > Florianopolis, Brazil: Biz from $2102 Econ from $808. – Jan-Mar

ORD > Florianopolis, Brazil: Biz from $2102 Econ from $808. – Jan-Mar

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

ORD > George Town, Cayman Islands: Biz from $619 Econ from $320. – Nov-Jan 

ORD > George Town, Cayman Islands: Biz from $619 Econ from $320. – Nov-Jan 

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

ORD > Cape Town, South Africa: Econ from $1000. – Oct-Dec 

ORD > Cape Town, South Africa: Econ from $1000. – Oct-Dec  [SOLD OUT]

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

ORD > Male, Maldives: Econ from $942. – Oct-Dec 

ORD > Male, Maldives: Econ from $942. – Oct-Dec  [SOLD OUT]

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

ORD > Abu Dhabi, United Arab Emirates: Econ from $796. – Oct-Dec

ORD > Abu Dhabi, United Arab Emirates: Econ from $796. – Oct-Dec

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

ORD > Rabat, Morocco: Econ from $556. – Nov-Jan (Including Thanksgiving)

ORD > Rabat, Morocco: Econ from $556. – Nov-Jan (Including Thanksgiving)

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

ORD > Bangkok, Thailand: Econ from $674. – Jun-Aug (Including Fourth of July and Summer Break) 

ORD > Bangkok, Thailand: Econ from $674. – Jun-Aug (Including Fourth of July and Summer Break) 

* There only appear to be a few seats at this price and availability is spotty. It will take a…

ORD > Auckland, New Zealand: Econ from $1068. – Oct-Dec

ORD > Auckland, New Zealand: Econ from $1068. – 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 > Phu Quoc, Vietnam: Econ from $845. – Oct-Dec 

ORD > Phu Quoc, Vietnam: Econ from $845. – Oct-Dec  [SOLD OUT]

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

ORD > Innsbruck, Austria: Econ from $595. – Jan-Mar (Presidents day Weekend) 

ORD > Innsbruck, Austria: Econ from $595. – 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 > Tokyo, Japan: Econ from $741. – Apr-Jun

ORD > Tokyo, Japan: Econ from $741. – Apr-Jun

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

ORD > Cape Town, South Africa: Econ from $1009. – Oct-Dec

ORD > Cape Town, South Africa: Econ from $1009. – Oct-Dec

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

ORD > Florianopolis, Brazil: Biz from $1367 Econ from $716. – Jan-Mar

ORD > Florianopolis, Brazil: Biz from $1367 Econ from $716. – 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 > Male, Maldives: Econ from $940. – Dec-Feb 

ORD > Male, Maldives: Econ from $940. – Dec-Feb 

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

ORD > Krabi, Thailand: Econ from $920.- Sep-Nov (Including Fall Break)

ORD > Krabi, Thailand: Econ from $920.- Sep-Nov (Including Fall 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 > Nairobi, Kenya: Econ from $813.- Oct-Dec

ORD > Nairobi, Kenya: Econ from $813.- Oct-Dec

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

ORD > Cagliari, Italy: Econ from $699.- Sep-Nov

ORD > Cagliari, Italy: Econ from $699.- Sep-Nov [SOLD OUT]

Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…

MDW > Zagreb, Croatia: Econ from $608.- Oct-Dec (Including Fall Break)

MDW > Zagreb, Croatia: Econ from $608.- Oct-Dec (Including Fall Break) [SOLD OUT]

* There only appear to be a few seats at this price and availability is spotty. It will take a…

ORD > Innsbruck, Austria: Econ from $551. – Jan-Mar (Presidents day Weekend) 

ORD > Innsbruck, Austria: Econ from $551. – 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…

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