Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
MDW > Charlotte, North Carolina: Econ from $139. – Nov-Jan [SOLD OUT]
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
ORD > Luqa, Malta: Econ from $464. – 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 > George Town, Cayman Islands: Biz from $616 Econ from $311. – 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 > Algiers, Algeria: Econ from $580. – Nov-Jan (Including Thanksgiving) [SOLD OUT]
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
MDW > Krakow, Poland: Econ from $526. – 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 > Dallas, Texas: Biz from $211 Econ from $90.- Nov-Jan [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Liberia, Costa Rica: Biz from $1190 Econ from $369. – Nov-Jan [SOLD OUT]
When I went to Costa Rica, I flew into Liberia. Nothing special there, but you’re only about a half-hour from…