Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
MDW > San Salvador, El Salvador: Econ from $286. – 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 > Malaga, Spain: Econ from $390. – 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 > Auckland, New Zealand: Econ from $810. – Feb-Apr
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Belize City, Belize: Biz from $640. Econ from $303. – Dec-Feb [SOLD OUT]
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
ORD > Entebbe, Uganda: Econ from $870.- Mar-May
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > George Town, Cayman Islands: Biz from $555 Econ from $293.- 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 > Prague, Czech Republic: Econ from $410.- Dec-Feb [SOLD OUT]
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Phuket City, Thailand: Econ from $624.- Jan-Mar (Presidents day Weekend)
* There only appear to be a few seats at this price and availability is spotty. It will take a…
ORD > Gdansk, Poland: Econ from $389.- Jan-Mar [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
MDW > San Juan, Puerto Rico: Econ from $181.- 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 $627.- Feb-Apr
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Dublin, Ireland: Biz from $1056 Econ from $346.- Dec-Feb [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Cartagena, Colombia: Biz from $596 Econ from $251.- 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 $765 Econ from $330.- 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 > Cluj Napoca, Romania: Econ from $515.- Mar-May (Including Spring Break)
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Dubai, United Arab Emirates: Econ from $589.- 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 > Larnaca, Cyprus: Econ from $493.- 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 > Budapest, Hungary: Econ from $421.- Feb-Apr
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Cozumel, Mexico: Biz from $1003 Econ from $246.- Feb-Apr
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 $885. – 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 > Liberia, Costa Rica: Biz from $1038. Econ from $371. – Feb-Apr (Including Spring Break)
When I went to Costa Rica, I flew into Liberia. Nothing special there, but you’re only about a half-hour from…
ORD > Bucharest, Romania: Econ from $523. – 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…
MDW > Wroclaw, Poland: Econ from $491. – Jan-Mar
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Kralendijk, Caribbean Netherlands: Biz from $1508. Econ from $451. – Feb-Apr [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 $887. – 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 > Colombo, Sri Lanka: Econ from $735. – Mar-May (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 > Luqa, Malta: Econ from $492. – 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 > Guatemala City, Guatemala: Biz from $703 Econ from $225. – Mar-May
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Montego Bay, Jamaica: Biz from $566 Econ from $299.- Nov-Jan (Including Winter Break) [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Poznan, Poland: Econ from $385.- Feb-Apr (Including Spring Break)
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 $519.- 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 > Barcelona, Spain: Econ from $355.- Mar-May
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Marrakesh, Morocco: Econ from $509.- 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 > Managua, Nicaragua: Biz from $520 Econ from $214.- Nov-Jan [SOLD OUT]
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 $534.- Mar-May
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Krakow, Poland: Econ from $388. – Jan-Mar (Presidents day Weekend)
Want to stretch your vacation dollars two to three times farther? Consider Eastern Europe over Western Europe. You’ll stretch your…
ORD > Cancun, Mexico: Biz from $530 Econ from $202.- Dec-Feb [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
MDW > Casablanca, Morocco: Econ from $780. – Feb-Apr
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
MDW > Guadalajara, Mexico: Biz from $677 Econ from $301. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…