Be sure to check the flight plus hotel price below! Sometimes, you can get your hotel for nearly free –…
ORD > Montego Bay, Jamaica: Biz from $513 Econ from $276.- Jan-Mar
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 $524 Econ from $248.- Dec-Feb
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > San Juan, Puerto Rico: Econ from $180. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Coxen Hole, Honduras: Biz from $952. Econ from $472. – Dec-Feb (Including MLK Weekend)
A lot of people are concerned about travel to Honduras, but Coxen Hole (AKA “Roatan”) is an island off of…
ORD > Kingston, Jamaica: Biz from $930 Econ from $355. – Dec-Feb
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 $1074. – Dec-Feb (Including MLK Weekend)
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Cozumel, Mexico: Biz from $1025 Econ from $332. – Aug-Oct
Cozumel is a completely separate part of mexico, and if you’ve ever thought about scuba diving, there isn’t a more…
ORD > Male, Maldives: Econ from $919.- 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 > Colombo, Sri Lanka: Econ from $748. – 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 > Kralendijk, Caribbean Netherlands: Biz from $1284 Econ from $519. – Dec-Feb
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Larnaca, Cyprus: Econ from $452. – Mar-May
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Nassau, The Bahamas: Biz from $810. Econ from $240. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Mykonos, Greece: Econ from $587. – Jan-Mar
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Montego Bay, Jamaica: Biz from $537 Econ from $289.- Dec-Feb
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Corfu, Greece: Econ from $692. – 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 > Auckland, New Zealand: Econ from $810. – Feb-Apr
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 $555 Econ from $293.- Dec-Feb
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
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…
MDW > San Juan, Puerto Rico: Econ from $181.- Dec-Feb
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 $765 Econ from $330.- Dec-Feb
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
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 > Cozumel, Mexico: Biz from $1003 Econ from $246.- Feb-Apr
Cozumel is a completely separate part of mexico, and if you’ve ever thought about scuba diving, there isn’t a more…
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 > Kralendijk, Caribbean Netherlands: Biz from $1508. Econ from $451. – Feb-Apr
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 > Colombo, Sri Lanka: Econ from $735. – Mar-May (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 > Luqa, Malta: Econ from $492. – Jan-Mar
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Montego Bay, Jamaica: Biz from $566 Econ from $299.- Nov-Jan (Including Winter Break)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
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…
ORD > Thera, Greece: Econ from $674. – Feb-Apr
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Willemstad, Curaçao: Biz from $1080. Econ from $428. – Nov-Jan
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 $596 Econ from $287. – Nov-Jan
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 $660 Econ from $305. – Dec-Feb
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Palma de Mallorca, Spain: Econ from $414. – 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 > Cozumel, Mexico: Biz from $1071 Econ from $323. – Jan-Mar
Cozumel is a completely separate part of mexico, and if you’ve ever thought about scuba diving, there isn’t a more…
ORD > Philadelphia, Pennsylvania: Biz from $327 Econ from $101. – Nov-Jan
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
MDW > San Juan, Puerto Rico: Econ from $138. – Dec-Feb
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 $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 > Phuket City, Thailand: Econ from $562.- Mar-May
* There only appear to be a few seats at this price and availability is spotty. It will take a…