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 $884 Econ from $206. – Sep-Nov
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 $1028 Econ from $204. – Sep-Nov
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 $634. – 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…
MDW > Jacksonville, Florida: Econ from $108. – Oct-Dec
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > San Jose, Costa Rica: Biz from $1171 Econ from $213. – Oct-Dec
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 $1101 Econ from $322. – Oct-Dec
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 $341. – Feb-Apr (Including Spring Break)
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Dubai, United Arab Emirates: Econ from $591. – Jan-Mar
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 $929 Econ from $328. – 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: Econ from $48. – Aug-Oct
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
MDW > San Pedro Sula, Honduras: Biz from $1076 Econ from $291. – 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 > Fort Lauderdale, Florida: Econ from $66. – Sep-Nov
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
MDW > San Juan, Puerto Rico: Econ from $124. – Aug-Oct
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Willemstad, Curaçao: Biz from $1172 Econ from $444. – 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 $647. – 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 > Cozumel, Mexico: Biz from $896 Econ from $199. – Sep-Nov
Cozumel is a completely separate part of mexico, and if you’ve ever thought about scuba diving, there isn’t a more…
ORD > Thera, Greece: Econ from $633. – 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 > Heraklion, Greece: Econ from $634. – 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…
MDW > Punta Cana, Dominican Republic: Econ from $234. – Oct-Dec
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 $643. – Jan-Mar
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
ORD > Oranjestad, Aruba: Econ from $302. – Aug-Oct
Our trip to Aruba was the beginning of JGOOT. I stumbled across ridiculously cheap flights, bundled that with quite a…
ORD > Corfu, Greece: Econ from $642. – 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…
MDW > Los Angeles, California: Econ from $77. – Oct-Dec
Have you ever booked a cruise only to find out that the flight to get there was going to be…
ORD > Pointe La Rue, Seychelles: Econ from $816. – Nov-Jan
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Piarco, Trinidad and Tobago: Biz from $934 Econ from $306. – Aug-Oct
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Boston, Massachusetts: Biz from $387 Econ from $47. – Sep-Nov (Including Fall Break)
I rarely post trips to Boston because they are typically so expensive and I advise using points instead of paying…
ORD > San Salvador, El Salvador: Biz from $841 Econ from $236. – Nov-Jan
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. – Sep-Nov
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
ORD > Myrtle Beach, South Carolina: Econ from $45. – Aug-Oct
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Cancun, Mexico: Biz from $731 Econ from $199. – Sep-Nov
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Miami, Florida: Econ from $55. – 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 > Kingston, Jamaica: Biz from $788 Econ from $277. – Aug-Oct
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: Biz from $974 Econ from $282. – 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: Biz from $994 Econ from $215. – Aug-Oct
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: Econ from $173. – Jan-Mar
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 $353. – Feb-Apr (Including Spring Break)
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Dubai, United Arab Emirates: Econ from $609. – Oct-Dec (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 > San Jose, Costa Rica: Biz from $1118 Econ from $211. – 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.…
MDW > Jacksonville, Florida: Biz from $521 Econ from $120. – Aug-Oct
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…