* This is a “fare dump” with a few alternate dates available.
ORD > Florianopolis, Brazil: Econ from $716. – 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…
ORD > Malaga, Spain: Econ from $416.- Feb-Apr
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Riga, Latvia: Econ from $509.- Jan-Mar [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 > Montego Bay, Jamaica: Biz from $531 Econ from $278.- Jan-Mar (Presidents day Weekend)
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 $287 Econ from $117.- Jan-Mar
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 $455 Econ from $196.- Feb-Apr
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > George Town, Cayman Islands: Biz from $461 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.…
MDW > Barcelona, Spain: Econ from $492. – Feb-Apr
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 $588 Econ from $237. – Feb-Apr
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 $456 Econ from $211. – Jan-Mar (Presidents day Weekend)
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 $176.- Jan-Mar [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 $490 Econ from $214.- 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.…
MDW > Dubai, United Arab Emirates: Econ from $730.- Jan-Mar (Presidents day Weekend)
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > San Salvador, El Salvador: Biz from $402 Econ from $180.- 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 > Boracay, Philippines: Econ from $855. – Aug-Oct
Have I mentioned that the Philippines has some of the best diving in the world? The beaches are amazing too.…
ORD > Fort Lauderdale, Florida: Biz from $278 Econ from $64. – Dec-Feb (Including MLK Weekend) [SOLD OUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Cozumel, Mexico: Biz from $1125 Econ from $332. – Feb-Apr (Including Spring Break)
Cozumel is a completely separate part of mexico, and if you’ve ever thought about scuba diving, there isn’t a more…
MDW > Lisbon, Portugal: Econ from $501.- Jan-Mar (Presidents day Weekend)
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Kingston, Jamaica: Biz from $650 Econ from $337.- Jan-Mar [SOLD OUT]
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 > Fort Myers, Florida: Biz from $265 Econ from $59.- Jan-Mar
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
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 > Riga, Latvia: Econ from $460.- Jan-Mar [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 > 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 > Chennai, India: Econ from $604.- Feb-Apr
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 $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.…