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 [SOLD OUT]
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) [SOLD OUT]
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 [SOLD OUT]
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 [SOLD OUT]
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 [SOLD OUT]
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 [SOLD OUT]
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 [SOLD OUT]
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 [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 > 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…
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 [SOLD OUT]
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)
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 [SOLD OUT]
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) [SOLD OUT]
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 [SOLD OUT]
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 [SOLD OUT]
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 [SOLD OUT]
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 [SOLD OUT]
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)
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 [SOLD OUT]
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) [SOLD OUT]
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 [SOLD OUT]
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 [SOLD OUT]
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 [SOLD OUT]
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 [SOLD OUT]
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)
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 [SOLD OUT]
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 [SOLD OUT]
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)
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 [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 > Kralendijk, Caribbean Netherlands: Biz from $1168 Econ from $573. – 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 > George Town, Cayman Islands: Biz from $619 Econ from $320. – 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 > Heraklion, Greece: Econ from $642. – Oct-Dec [SOLD OUT]
Be sure to check the flight plus hotel price below! Sometimes, you can get your hotel for nearly free –…