Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Porto, Portugal: Econ from $395. – Dec-Feb
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Guatemala City, Guatemala: Biz from $836 Econ from $231. – 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 $643. – 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 > Myrtle Beach, South Carolina: Econ from $83. – Aug-Oct
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
MDW > Punta Cana, Dominican Republic: Biz from $955 Econ from $236. – Jul-Sep
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 $66. – Jul-Sep
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 $470. – Aug-Oct (Including Labor Day)
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
ORD > Boston, Massachusetts: Biz from $427 Econ from $43. – Aug-Oct
I rarely post trips to Boston because they are typically so expensive and I advise using points instead of paying…
ORD > Pointe La Rue, Seychelles: Econ from $818. – Nov-Jan (Including Thanksgiving)
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Cancun, Mexico: Biz from $721 Econ from $185. – Sep-Nov
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
MDW > San Jose, Costa Rica: Biz from $1168 Econ from $273. – Jul-Sep
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 $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 > Santo Domingo, Dominican Republic: Biz from $745 Econ from $312. – 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 $86. – Jul-Sep (Including Summer Break)
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Luqa, Malta: Econ from $563. – Nov-Jan (Including Thanksgiving)
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 $256. – 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 $488. – Aug-Oct
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
ORD > Kingston, Jamaica: Biz from $853 Econ from $336. – 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 $562. – Sep-Nov (Including Fall Break)
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
MDW > San Francisco, California: Econ from $81. – Sep-Nov
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > San Salvador, El Salvador: Biz from $756 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 > Colombo, Sri Lanka: Econ from $845. – Oct-Dec
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Barcelona, Spain: Econ from $356. – Oct-Dec
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
MDW > San Juan, Puerto Rico: Econ from $168. – 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 > Heraklion, Greece: Econ from $662. – Oct-Dec (Including Fall Break)
Be sure to check the flight plus hotel price below! Sometimes, you can get your hotel for nearly free –…
ORD > Buenos Aires, Argentina: Econ from $831. – Jul-Sep
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Sao Paulo, Brazil: Econ from $642. – Jul-Sep
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Rio de Janeiro, Brazil: Econ from $599. – Sep-Nov
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Tampa, Florida: Econ from $64. – Sep-Nov
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > San Pedro Sula, Honduras: Biz from $715 Econ from $241. – Sep-Nov
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 $450 Econ from $87. – Aug-Oct
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
MDW > Guatemala City, Guatemala: Biz from $777 Econ from $304. – 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 $809. – Jul-Sep
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Las Palmas de Gran Canaria, Spain: Econ from $490. – Oct-Dec
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Punta Cana, Dominican Republic: Biz from $755 Econ from $246. – Aug-Oct
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Montego Bay, Jamaica: Biz from $1099 Econ from $342. – Sep-Nov
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 $713. – Sep-Nov (Including Fall Break)
Be sure to check the flight plus hotel price below! Sometimes, you can get your hotel for nearly free –…
MDW > San Jose, Costa Rica: Econ from $329. – Jul-Sep
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 $347. – Jul-Sep
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…