For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
MDW > Wroclaw, Poland: Econ from $492.- Dec-Feb [SOLD OUT] [SOLD OUT]
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 $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 > Innsbruck, Austria: Econ from $700. – Jan-Mar [SOLD OUT]
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Ontario, California: Econ from $171. – Dec-Feb (Including MLK Weekend) [SOLD OUT]
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
ORD > Nashville, Tennessee: Biz from $323 Econ from $133.- Dec-Feb (Including MLK Weekend) [SOLD OUT]
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
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…
MDW > Budapest, Hungary: Econ from $517.- Mar-May
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Madrid, Spain: Econ from $387.- Dec-Feb (Including MLK Weekend) [SOLD OUT]
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Casablanca, Morocco: Econ from $549.- 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 > 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 > 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 > Las Vegas, Nevada: Econ from $110.- Apr-Jun (Including Summer Break)
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
ORD > Bogota, Colombia: Biz from $601 Econ from $264.- Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Kochi, India: Econ from $679.- Feb-Apr (Including Spring Break)
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Gdansk, Poland: Biz from $1767 Econ from $424.- Jan-Mar [SOLD OUT]
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
MDW > Poznan, Poland: Econ from $491.- Mar-May
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
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 > San Diego, California: Econ from $151.- Dec-Feb (Including MLK Weekend) [SOLD OUT]
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Cairo, Egypt: Econ from $642.- Feb-Apr (Including Spring Break)
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
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.…
MDW > Bucharest, Romania: Econ from $577.- 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 > 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 > 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 > Belgrade, Serbia: Econ from $516.- Mar-May
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
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 > Krakow, Poland: Econ from $390.- 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 > 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 > Phoenix, Arizona: Econ from $57.- Feb-Apr
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Athens, Greece: Econ from $452.- Jan-Mar
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Algiers, Algeria: Econ from $549.- 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 > 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.…