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 $702. – Oct-Dec (Including Thanksgiving)
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 $911 Econ from $238. – Mar-May
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Kralendijk, Caribbean Netherlands: Biz from $1181 Econ from $588. – Mar-May
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 $889 Econ from $231. – Mar-May
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Piarco, Trinidad and Tobago: Econ from $401. – Mar-May
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 $718 Econ from $318. – Mar-May
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 $629. – Mar-May
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
MDW > Punta Cana, Dominican Republic: Econ from $251. – Apr-Jun
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 $591. – Nov-Jan (Including Thanksgiving)
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 $1003 Econ from $261. – Mar-May
Our trip to Aruba was the beginning of JGOOT. I stumbled across ridiculously cheap flights, bundled that with quite a…
ORD > Thera, Greece: Econ from $507. – Mar-May
Be sure to check the flight plus hotel price below! Sometimes, you can get your hotel for nearly free –…
ORD > Kralendijk, Caribbean Netherlands: Biz from $1498 Econ from $588. – Mar-May
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 $668. – Mar-May
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 $911 Econ from $234. – Mar-May
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 $1166. – Mar-May
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Male, Maldives: Econ from $903. – Oct-Dec
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Kingston, Jamaica: Biz from $738 Econ from $310. – Mar-May
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 $763. – Jul-Sep
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Cozumel, Mexico: Biz from $645 Econ from $172. – Apr-Jun
Cozumel is a completely separate part of mexico, and if you’ve ever thought about scuba diving, there isn’t a more…
MDW > San Juan, Puerto Rico: Biz from $804 Econ from $147. – Apr-Jun
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 $687. – Apr-Jun
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Punta Cana, Dominican Republic: Biz from $755 Econ from $179. – Mar-May
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 $648. – Sep-Nov (Including Fall Break)
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Thera, Greece: Econ from $686. – Mar-May
Be sure to check the flight plus hotel price below! Sometimes, you can get your hotel for nearly free –…
ORD > Oranjestad, Aruba: Biz from $1124 Econ from $255. – Feb-Apr (Including Spring Break)
When we went to Aruba – we stayed at the Renaissance, and it was fantastic. They have their own private…
ORD > Kralendijk, Caribbean Netherlands: Biz from $1760 Econ from $538. – Mar-May
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 $698. – Mar-May
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
MDW > Saint Thomas Island, U.S. Virgin Islands: Econ from $181. – Mar-May
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 $760. – Aug-Oct
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 $911 Econ from $253. – Feb-Apr (Including Spring Break)
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 $965. – Mar-May
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > San Juan, Puerto Rico: Biz from $804 Econ from $162. – Apr-Jun
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 $818 Econ from $325. – Feb-Apr (Including Spring Break)
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 $580. – Mar-May
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 $641 Econ from $244. – Mar-May
Cozumel is a completely separate part of mexico, and if you’ve ever thought about scuba diving, there isn’t a more…
MDW > Punta Cana, Dominican Republic: Biz from $960 Econ from $210. – Mar-May
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Reykjavik, Iceland: Econ from $397. – Nov-Jan (Including Thanksgiving)
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Thera, Greece: Econ from $689. – Mar-May
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Oranjestad, Aruba: Biz from $1038 Econ from $261. – Feb-Apr (Including Spring Break)
If you visit Aruba, be sure to visit Flying Fishbone. Best dining experience Michelle and I have ever had. *…