Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Cartagena, Colombia: Biz from $574 Econ from $229.- Dec-Feb [SOLD OUT]
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 $591.- Mar-May
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Guatemala City, Guatemala: Biz from $685 Econ from $207.- Apr-Jun
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Palanga, Lithuania: Biz from $2242 Econ from $436.- Jan-Mar [SOLD OUT]
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Colombo, Sri Lanka: Econ from $748.- Feb-Apr (Including Spring Break)
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
MDW > Miami, Florida: Econ from $57.- Jan-Mar
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Luqa, Malta: Econ from $515.- Jan-Mar [SOLD OUT]
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 $475 Econ from $229.- Dec-Feb [SOLD OUT]
When we went to Aruba – we stayed at the Renaissance, and it was fantastic. They have their own private…
ORD > Los Angeles, California: Econ from $106.- Dec-Feb [SOLD OUT]
Have you ever booked a cruise only to find out that the flight to get there was going to be…
ORD > Belize City, Belize: Biz from $521 Econ from $281.- Jan-Mar
* There only appear to be a few seats at this price and availability is spotty. It will take a…
ORD > Mykonos, Greece: Econ from $639.- Jul-Sep
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 $513 Econ from $276.- Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Cancun, Mexico: Biz from $386 Econ from $198.- Jan-Mar [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Boston, Massachusetts: Biz from $289 Econ from $127.- Dec-Feb [SOLD OUT]
I rarely post trips to Boston because they are typically so expensive and I advise using points instead of paying…
ORD > Malaga, Spain: Econ from $376.- Jan-Mar [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > George Town, Cayman Islands: Biz from $524 Econ from $248.- Dec-Feb [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Managua, Nicaragua: Biz from $436 Econ from $211.- Dec-Feb (Including MLK Weekend) [SOLD OUT]
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 $460 Econ from $229.- Dec-Feb [SOLD OUT]
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 $352.
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > San Salvador, El Salvador: Biz from $446 Econ from $216.- Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > San Juan, Puerto Rico: Econ from $180. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Coxen Hole, Honduras: Biz from $952. Econ from $472. – Dec-Feb (Including MLK Weekend) [SOLD OUT]
A lot of people are concerned about travel to Honduras, but Coxen Hole (AKA “Roatan”) is an island off of…
ORD > Fort Lauderdale, Florida: Biz from $333 Econ from $56. – Jan-Mar (Presidents day Weekend)
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 $589. – Dec-Feb (Including MLK Weekend) [SOLD OUT]
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Cartagena, Colombia: Biz from $625 Econ from $247. – Dec-Feb [SOLD OUT]
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 $930 Econ from $355. – Dec-Feb [SOLD OUT]
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 $1074. – Dec-Feb (Including MLK Weekend) [SOLD OUT]
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Cozumel, Mexico: Biz from $1025 Econ from $332. – Aug-Oct
Cozumel is a completely separate part of mexico, and if you’ve ever thought about scuba diving, there isn’t a more…
ORD > Male, Maldives: Econ from $919.- Feb-Apr (Including Spring Break)
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
MDW > Miami, Florida: Econ from $47.- Jan-Mar
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Oranjestad, Aruba: Biz from $486 Econ from $238.- Dec-Feb [SOLD OUT]
Our trip to Aruba was the beginning of JGOOT. I stumbled across ridiculously cheap flights, bundled that with quite a…
ORD > Colombo, Sri Lanka: Econ from $748. – Feb-Apr (Including Spring Break)
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Kralendijk, Caribbean Netherlands: Biz from $1284 Econ from $519. – Dec-Feb [SOLD OUT]
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 $452. – Mar-May
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Los Angeles, California: Biz from $367. Econ from $135. – Nov-Jan (Including Winter Break) [SOLD OUT]
Have you ever booked a cruise only to find out that the flight to get there was going to be…
ORD > Nassau, The Bahamas: Biz from $810. Econ from $240. – 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 $587. – Jan-Mar
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Lisbon, Portugal: Econ from $369.- 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 > Cancun, Mexico: Biz from $510 Econ from $200.- Dec-Feb [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…