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 $612. – Oct-Dec
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 $877. Econ from $249. – Sep-Nov (Including Fall Break)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > San Juan, Puerto Rico: Biz from $743. Econ from $132. – Sep-Nov
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Fort Lauderdale, Florida: Econ from $71. – Aug-Oct
Be sure to check out the “cruises” link below to see if you could take advantage of this cheap flight,…
ORD > Puerto Escondido, Mexico: Econ from $247. – 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 $613. – 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 > San Francisco, California: Econ from $126. – Aug-Oct
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Thera, Greece: Econ from $614. – Sep-Nov (Including Fall Break)
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > San Jose del Cabo, Mexico: Econ from $272. – Jan-Mar
When you go to Cabo, you’ll get approached by dozens of locals offering the best deals possible for snorkeling, sailing,…
ORD > Rijeka, Croatia: Econ from $725. – Aug-Oct
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Oakland, California: Econ from $97. – Aug-Oct
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
ORD > Mykonos, Greece: Econ from $653. – Sep-Nov
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Managua, Nicaragua: Biz from $868. Econ from $281. – Sep-Nov (Including Fall Break)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Los Angeles, California: Econ from $75. – Aug-Oct
Beaches, Hollywood, 5 amusement parks, home to the Lakers, Dodgers, Rams, Ducks, Kings, Angels, and quick access to Mexico cruises…
ORD > Split, Croatia: Econ from $490. – Oct-Dec
* This is a “fare dump” with a few alternate dates available.
ORD > Pointe La Rue, Seychelles: Econ from $889. – Nov-Jan
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Boston, Massachusetts: Biz from $387 Econ from $43. – Oct-Dec
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
ORD > Cancun, Mexico: Biz from $711 Econ from $204. – Aug-Oct
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Myrtle Beach, South Carolina: Biz from $480 Econ from $80. – Aug-Oct
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Piarco, Trinidad and Tobago: Biz from $914 Econ from $422. – Oct-Dec
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 $562. – 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 > San Salvador, El Salvador: Biz from $724 Econ from $264. – Aug-Oct
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Port Au Prince, Haiti: Biz from $835 Econ from $286. – Aug-Oct (Including Labor Day)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Miami, Florida: Econ from $52. – Jul-Sep
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Kingston, Jamaica: Biz from $998 Econ from $278.- Jul-Sep
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Colombo, Sri Lanka: Econ from $832. – Aug-Oct
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Oranjestad, Aruba: Biz from $1074 Econ from $290. – Jul-Sep
Our trip to Aruba was the beginning of JGOOT. I stumbled across ridiculously cheap flights, bundled that with quite a…
MDW > Saint Thomas Island, U.S. Virgin Islands: Econ from $220. – Jul-Sep
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Jacksonville, Florida: Biz from $478 Econ from $144. – Jul-Sep
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Larnaca, Cyprus: Econ from $622. – 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 > Dubrovnik, Croatia: Econ from $554. – Oct-Dec (Including Thanksgiving)
* This is a “fare dump” with a few alternate dates available.
ORD > San Juan, Puerto Rico: Biz from $794 Econ from $161. – Aug-Oct
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Barcelona, Spain: Econ from $345. – Dec-Feb
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Montego Bay, Jamaica: Biz from $950 Econ from $243. – Jul-Sep
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 $625. – 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 > Christiansted, U.S. Virgin Islands: Biz from $896 Econ from $270. – Jul-Sep
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 $643. – Jul-Sep
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Managua, Nicaragua: Biz from $836 Econ from $296. – Jul-Sep
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > San Pedro Sula, Honduras: Biz from $800 Econ from $258. – Sep-Nov (Including Fall Break)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…