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ORD > Larnaca, Cyprus: Econ from $496.- Jan-Mar

ORD > Larnaca, Cyprus: Econ from $496.- Jan-Mar

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

ORD > Oranjestad, Aruba: Biz from $554 Econ from $247.- Nov-Jan

ORD > Oranjestad, Aruba: Biz from $554 Econ from $247.- Nov-Jan

When we went to Aruba – we stayed at the Renaissance, and it was fantastic. They have their own private…

ORD > Colombo, Sri Lanka: Econ from $774. – Mar-May (Including Spring Break) 

ORD > Colombo, Sri Lanka: Econ from $774. – Mar-May (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 > Kingston, Jamaica: Biz from $805 Econ from $367. – Jan-Mar 

ORD > Kingston, Jamaica: Biz from $805 Econ from $367. – Jan-Mar 

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

ORD > Montego Bay, Jamaica: Biz from $610 Econ from $298.- Dec-Feb (Including MLK Weekend)

ORD > Montego Bay, Jamaica: Biz from $610 Econ from $298.- 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 > Luqa, Malta: Econ from $544. – Nov-Jan

MDW > Luqa, Malta: Econ from $544. – Nov-Jan

Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…

MDW > Saint Thomas Island, U.S. Virgin Islands: Econ from $275. – Dec-Feb

MDW > Saint Thomas Island, U.S. Virgin Islands: Econ from $275. – Dec-Feb

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

ORD > Santo Domingo, Dominican Republic: Biz from $521. Econ from $292. – Nov-Jan

ORD > Santo Domingo, Dominican Republic: Biz from $521. Econ from $292. – Nov-Jan

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

ORD > Kos, Greece: Econ from $667. – Nov-Jan

ORD > Kos, Greece: Econ from $667. – Nov-Jan

Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…

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 > Oranjestad, Aruba: Biz from $957 Econ from $311. – Dec-Feb

ORD > Oranjestad, Aruba: Biz from $957 Econ from $311. – Dec-Feb

When we went to Aruba – we stayed at the Renaissance, and it was fantastic. They have their own private…

MDW > Simpson Bay, St. Maarten: Econ from $375. – Oct-Dec (Including Thanksgiving)

MDW > Simpson Bay, St. Maarten: Econ from $375. – Oct-Dec (Including Thanksgiving)

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

ORD > Kingston, Jamaica: Biz from $925. Econ from $352. – Nov-Jan

ORD > Kingston, Jamaica: Biz from $925. Econ from $352. – Nov-Jan

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

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 > Colombo, Sri Lanka: Econ from $733. – Oct-Dec

ORD > Colombo, Sri Lanka: Econ from $733. – Oct-Dec

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

ORD > Punta Cana, Dominican Republic: Econ from $201. – Nov-Jan 

ORD > Punta Cana, Dominican Republic: Econ from $201. – Nov-Jan 

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

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…

MDW > Willemstad, Curaçao: Biz from $1399 Econ from $454. – Nov-Jan

MDW > Willemstad, Curaçao: Biz from $1399 Econ from $454. – Nov-Jan

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

ORD > Luqa, Malta: Econ from $397. – Nov-Jan 

ORD > Luqa, Malta: Econ from $397. – Nov-Jan 

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

ORD > Palma de Mallorca, Spain: Econ from $402. – Feb-Apr (Including Spring Break)

ORD > Palma de Mallorca, Spain: Econ from $402. – 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 > 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 > 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 > 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 > 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 > 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 > Montego Bay, Jamaica: Biz from $535 Econ from $266.- Oct-Dec

ORD > Montego Bay, Jamaica: Biz from $535 Econ from $266.- Oct-Dec [SOLD OUT]

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

ORD > Oranjestad, Aruba: Biz from $968. Econ from $346. – Nov-Jan

ORD > Oranjestad, Aruba: Biz from $968. Econ from $346. – Nov-Jan

If you visit Aruba, be sure to visit Flying Fishbone. Best dining experience Michelle and I have ever had. *…

ORD > Punta Cana, Dominican Republic: Biz from $770 Econ from $205. – Dec-Feb (Including MLK Weekend) 

ORD > Punta Cana, Dominican Republic: Biz from $770 Econ from $205. – 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.…

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 > Willemstad, Curaçao: Biz from $1074. Econ from $350. – Oct-Dec

ORD > Willemstad, Curaçao: Biz from $1074. Econ from $350. – Oct-Dec

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

ORD > Luqa, Malta: Econ from $464. – Nov-Jan

ORD > Luqa, Malta: Econ from $464. – Nov-Jan

Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…

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 > Palma de Mallorca, Spain: Econ from $422. – Feb-Apr (Including Spring Break) 

ORD > Palma de Mallorca, Spain: Econ from $422. – 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…

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 > 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 > Heraklion, Greece: Econ from $549. – Oct-Dec (Including Fall Break)

ORD > Heraklion, Greece: Econ from $549. – Oct-Dec (Including Fall Break) [SOLD OUT]

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

ORD > Kingston, Jamaica: Biz from $780. Econ from $342. – Oct-Dec

ORD > Kingston, Jamaica: Biz from $780. Econ from $342. – Oct-Dec

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 $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 > Mykonos, Greece: Econ from $569. – Sep-Nov (Including Fall Break) 

ORD > Mykonos, Greece: Econ from $569. – Sep-Nov (Including Fall Break)  [SOLD OUT]

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

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