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 $586. – 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 > Santiago, Chile: Biz from $1990 Econ from $685. – Jul-Sep (Including Summer Break)
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Santo Domingo, Dominican Republic: Biz from $937 Econ from $282. – Jul-Sep
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Split, Croatia: Econ from $613. – Jul-Sep
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
ORD > Dubrovnik, Croatia: Econ from $567. – Sep-Nov
* This is a “fare dump” with a few alternate dates available.
ORD > Saint Thomas Island, U.S. Virgin Islands: Biz from $948 Econ from $212. – Jul-Sep (Including Summer Break)
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 $875. – Jan-Mar
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > San Francisco, California: Econ from $165. – Sep-Nov (Including Fall Break)
Beaches, Sunsets, Redwoods, Golden Gate Bridge, fine dining, night life, Lombard Street, & cable cars… San Francisco is one of…
ORD > Barcelona, Spain: Econ from $374. – Jul-Sep
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
MDW > San Juan, Puerto Rico: Econ from $161. – Jul-Sep (Including Summer Break)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Ponta Delgada, Portugal: Econ from $566. – Oct-Dec
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > San Salvador, El Salvador: Biz from $721 Econ from $255. – 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 > Heraklion, Greece: Econ from $662. – 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 > Buenos Aires, Argentina: Biz from $2172 Econ from $677. – Jul-Sep
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Managua, Nicaragua: Biz from $852 Econ from $226. – Aug-Oct
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Tampa, Florida: Econ from $64. – Jul-Sep (Including Summer Break)
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
ORD > San Pedro Sula, Honduras: Biz from $832 Econ from $285. – Jun-Aug (Including Summer Break)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Durban, South Africa: Econ from $1017. – Apr-Jun
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Corfu, Greece: Econ from $672. – Jul-Sep
Be sure to check the flight plus hotel price below! Sometimes, you can get your hotel for nearly free –…
ORD > Cartagena, Colombia: Biz from $869 Econ from $269. – Jul-Sep
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Guatemala City, Guatemala: Biz from $807 Econ from $213. – Aug-Oct
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Myrtle Beach, South Carolina: Biz from $437 Econ from $92. – Jul-Sep
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
MDW > Punta Cana, Dominican Republic: Econ from $239. – Jun-Aug (Including Summer Break)
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 $654. – Apr-Jun
Be sure to check the flight plus hotel price below! Sometimes, you can get your hotel for nearly free –…
ORD > Montego Bay, Jamaica: Biz from $928 Econ from $253. – Aug-Oct
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Bridgetown, Barbados: Econ from $259. – Aug-Oct
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 $315. – Aug-Oct
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Miami, Florida: Econ from $48. – Aug-Oct
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
MDW > Luqa, Malta: Econ from $532. – 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 > Santo Domingo, Dominican Republic: Biz from $822 Econ from $272. – Aug-Oct
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 $184. – Aug-Oct
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Split, Croatia: Econ from $499. – Apr-Jun
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
MDW > San Juan, Puerto Rico: Econ from $168. – May-Jul (Including Summer Break)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Barcelona, Spain: Econ from $455. – Nov-Jan
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
MDW > San Francisco, California: Econ from $78. – Aug-Oct
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
MDW > San Salvador, El Salvador: Biz from $840 Econ from $280. – 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 > Dubrovnik, Croatia: Econ from $547. – Sep-Nov (Including Fall Break)
* This is a “fare dump” with a few alternate dates available.
ORD > Ponta Delgada, Portugal: Econ from $585. – 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 > Colombo, Sri Lanka: Econ from $895. – Mar-May
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…