When we went to Aruba – we stayed at the Renaissance, and it was fantastic. They have their own private…
ORD > Thera, Greece: Econ from $698. – Sep-Nov
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Luqa, Malta: Econ from $563. – Apr-Jun
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Simpson Bay, St. Maarten: Econ from $247. – Feb-Apr
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Saint Thomas Island, U.S. Virgin Islands: Biz from $1078 Econ from $178. – 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 $973 Econ from $252. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Christiansted, U.S. Virgin Islands: 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 > Santo Domingo, Dominican Republic: Biz from $836 Econ from $243. – Jan-Mar (Including President’s Day Weekend)
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 $655. – Sep-Nov (Including Fall Break)
Be sure to check the flight plus hotel price below! Sometimes, you can get your hotel for nearly free –…
ORD > Reykjavik, Iceland: Biz from $908 Econ from $389. – Mar-May
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Kingston, Jamaica: Biz from $698 Econ from $296. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Pointe La Rue, Seychelles: Econ from $921. – 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 > Punta Cana, Dominican Republic: Biz from $751 Econ from $229. – Jan-Mar
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 $1044 Econ from $219. – Jan-Mar (Including President’s Day Weekend)
If you visit Aruba, be sure to visit Flying Fishbone. Best dining experience Michelle and I have ever had. *…
MDW > San Juan, Puerto Rico: Biz from $887 Econ from $126. – Jan-Mar
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 $634. – Mar-May
Be sure to check the flight plus hotel price below! Sometimes, you can get your hotel for nearly free –…
ORD > Palma de Mallorca, Spain: Econ from $536. – Aug-Oct
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
MDW > Christiansted, U.S. Virgin Islands: Econ from $184. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Saint Thomas Island, U.S. Virgin Islands: Econ from $178. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Simpson Bay, St. Maarten: Econ from $243. – Jan-Mar
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 $1028. – Aug-Oct (Including Labor Day)
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Christiansted, U.S. Virgin Islands: Econ from $184. – 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 $673. – Jul-Sep
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Kingston, Jamaica: Biz from $696 Econ from $295. – Dec-Feb
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 $621. – Feb-Apr
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
MDW > Punta Cana, Dominican Republic: Biz from $824 Econ from $239. – Jan-Mar
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 $1036 Econ from $218. – Jan-Mar
If you visit Aruba, be sure to visit Flying Fishbone. Best dining experience Michelle and I have ever had. *…
MDW > Montego Bay, Jamaica: Biz from $1075 Econ from $255. – Jan-Mar
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: Biz from $697 Econ from $117. – Dec-Feb
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Thera, Greece: Econ from $620. – Sep-Nov
Be sure to check the flight plus hotel price below! Sometimes, you can get your hotel for nearly free –…
ORD > Saint Thomas Island, U.S. Virgin Islands: Biz from $1036 Econ from $175. – 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: Biz from $797 Econ from $111. – 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 $405. – Aug-Oct
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Christiansted, U.S. Virgin Islands: Biz from $1058 Econ from $184. – Dec-Feb
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Honolulu, Hawaii: Econ from $321. – Dec-Feb
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
ORD > Aguadilla, Puerto Rico: Biz from $739. Econ from $145. – Jan-Mar
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 $820 Econ from $226. – Dec-Feb
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 $1113 Econ from $213. – Jan-Mar
When we went to Aruba – we stayed at the Renaissance, and it was fantastic. They have their own private…
ORD > Montego Bay, Jamaica: Biz from $974 Econ from $243. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Thera, Greece: Econ from $620. – Jul-Sep
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…